ORCID Profile
0000-0002-9713-9599
Current Organisation
University of Adelaide
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Research Topics
In Research Link Australia (RLA), "Research Topics" refer to ANZSRC FOR and SEO codes. These topics are either sourced from ANZSRC FOR and SEO codes listed in researchers' related grants or generated by a large language model (LLM) based on their publications.
Top 5 Research Topics
ANZSRC Field of Research (FoR)
Macromolecular and Materials Chemistry | Synthesis of Materials | Nanochemistry and Supramolecular Chemistry | Transition Metal Chemistry | Physical Chemistry (Incl. Structural) | Structural Chemistry and Spectroscopy | Mineralogy and Crystallography | Optical Physics | Organic Chemical Synthesis | Chemical Characterisation of Materials | Analytical Biochemistry | Transition Metal Chemistry | Solid State Chemistry | Supramolecular Chemistry | Materials engineering | Structural Chemistry | Reaction kinetics and dynamics | Biochemistry and Cell Biology | Organic Chemical Synthesis | Characterisation Of Macromolecules | Structural Biology (incl. Macromolecular Modelling) | Functional materials | Biophysics | Nanoscale characterisation | Photonics, Optoelectronics and Optical Communications | Analytical Spectrometry | Inorganic Chemistry | F-Block Chemistry | Optical Physics not elsewhere classified | Proteomics and Intermolecular Interactions (excl. Medical Proteomics) |
ANZSRC Socio-Economic Objective (SEO)
Expanding Knowledge in the Chemical Sciences | Chemical sciences | Biological sciences | Physical sciences | Expanding Knowledge in the Physical Sciences | Air Force | National Security | Treatments (e.g. chemicals, antibiotics) | Higher education | Inherited diseases (incl. gene therapy) | Expanding Knowledge in the Environmental Sciences | Diagnostic Methods | Expanding Knowledge in the Earth Sciences | Industrial Chemicals and Related Products not elsewhere classified | Expanding Knowledge in the Agricultural and Veterinary Sciences | Expanding Knowledge in the Biological Sciences
Related Links
Publications
A microstructured optical fiber sensor for ion-sensing based on the photoinduced electron transfer effect
Publisher: SPIE
Date: 31-01-2012
DOI: 10.1117/12.915959
Synthesis and crystal structure ofN-6-[(4-pyridylamino)carbonyl]-pyridine-2-carboxylic acid methyl ester zinc complex
Publisher: Informa UK Limited
Date: 17-03-2014
Staggered pillaring: a strategy to control layer–layer packing and enhance porosity in MOFs
Publisher: Informa UK Limited
Date: 08-04-2016
A bioinspired, one-step total synthesis of peshawaraquinone
Publisher: Royal Society of Chemistry (RSC)
Date: 2023
DOI: 10.1039/D2SC05377B
Abstract: A new proposal for the biosynthesis of peshawaraquinone via the unsymmetrical dimerization of dehydro-α-lapachone led to its total synthesis in one step from inexpensive starting materials.
Molecular design of amorphous porous organic cages for enhanced gas storage
Publisher: American Chemical Society (ACS)
Date: 04-2015
DOI: 10.1021/JP512944R
Probing post-synthetic metallation in metal-organic frameworks: Insights from X-ray crystallography
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C4CC09639H
Abstract: Post-synthetic metallation is a key route to modifying MOFs but as shown here the choice of solvent affects the extent of reaction and the form of the metallated product.
Hexa(2-pyridyl)[3]radialene: self-assembly of a hexanuclear silver array
Publisher: Royal Society of Chemistry (RSC)
Date: 22-01-2002
DOI: 10.1039/B109214F
Abstract: Reaction of the new ligand hexa(2-pyridyl)[3]radialene with silver tetrafluoroborate results in the formation of a M6L2 cage with an encapsulated mu 3-fluorido anion.
Elucidating pore chemistry within metal–organic frameworks via single crystal X-ray diffraction; from fundamental understanding to application
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D1CE00067E
Abstract: The application of metal–organic frameworks (MOFs) to erse chemical sectors is aided by their crystallinity, which permits the use of X-ray crystallography to characterise their pore chemistry and provides invaluable insight into their properties.
Mechanistic Studies on the Autoxidation of α-Guaiene: Structural Diversity of the Sesquiterpenoid Downstream Products
Publisher: American Chemical Society (ACS)
Date: 12-01-2015
DOI: 10.1021/NP500819F
Abstract: Two unstable hydroperoxides, 6b and 10a, and 13 downstream sesquiterpenoids have been isolated from the autoxidation mixture of the bicyclic sesquiterpene α-guaiene (1) on cellulose filter paper. One of the significant natural products isolated was rotundone (2), which is the only known impact odorant displaying a peppery aroma. Other products included corymbolone (4a) and its C-6 epimer 4b, the (2R)- and (2S)-rotundols (7a/b), and several hitherto unknown epimers of natural chabrolidione A, namely, 7-epi-chabrolidione A (3a) and 1,7-epi-chabrolidione A (3b). Two 4-hydroxyrotundones (8a/b) and a range of epoxides (9a/b and 5a/b) were also formed in significant amounts after autoxidation. Their structures were elucidated on the basis of spectroscopic data and X-ray crystallography, and a number of them were confirmed through total synthesis. The mechanisms of formation of the majority of the products may be accounted for by initial formation of the 2- and 4-hydroperoxyguaienes (6a/b and 10a/b) followed by various fragmentation or degradation pathways. Given that α-guaiene (1) is well known to exist in the essential oils of numerous plants, coupled with the fact that aerial oxidation to form this myriad of downstream oxidation products occurs readily at ambient temperature, suggests that many of them have been overlooked during previous isolation studies from natural sources.
Post-synthetic metalation of metal–organic frameworks
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C4CS00076E
Abstract: Post-synthetic metalation (PSMet) offers expansive scope for a targeted approach to tailoring the properties of MOFs.
Cyclometalated Compounds. XVII.1 The First Threefold Cyclopalladation of a Single Benzene Ring
Publisher: American Chemical Society (ACS)
Date: 07-05-2003
DOI: 10.1021/OM030110P
Enzyme Encapsulation in a Porous Hydrogen-Bonded Organic Framework
Publisher: American Chemical Society (ACS)
Date: 19-08-2019
DOI: 10.1021/JACS.9B06589
Abstract: Protection of biological assemblies is critical to applications in biotechnology, increasing the durability of enzymes in biocatalysis or potentially stabilizing biotherapeutics during transport and use. Here we show that a porous hydrogen-bonded organic framework (HOF) constructed from water-soluble tetra-amidinium (
Probing solid-state breathing and structural transformations in a series of silver(I) porous coordination polymers
Publisher: Wiley
Date: 02-07-2015
Norbornadiene‐Based Photoswitches with Exceptional Combination of Solar Spectrum Match and Long‐Term Energy Storage
Publisher: Wiley
Date: 16-08-2018
Abstract: Norbornadiene-quadricyclane (NBD-QC) photoswitches are candidates for applications in solar thermal energy storage. Functionally, they rely on an intramolecular [2+2] cycloaddition reaction, which couples the S
Desymmetrization and Kinetic Resolution of Endoperoxides Using a Bifunctional Organocatalyst
Publisher: American Chemical Society (ACS)
Date: 08-08-2023
Fluorescent hexaaryl- and hexa-heteroaryl[3]radialenes: Synthesis, structures, and properties
Publisher: Beilstein Institut
Date: 11-01-2012
DOI: 10.3762/BJOC.8.7
Abstract: The syntheses of three new [3]radialenes – hexakis(3,5-dimethylpyrazolyl)-, hexakis(3-cyanophenyl)-, and hexakis(3,4-dicyanophenyl)[3]radialene ( 1 – 3 ) – are reported. Compound 3 is obtained in five steps with an excellent yield of 76% in the key step. Compared to that, the respective steps of the syntheses of 1 and 2 result in lower yields. All compounds adopt a double bladed propeller conformation in solution. Compound 3 is considerably more electron deficient than previously reported hexaaryl[3]radialenes, with reduction potentials of −0.06 and −0.45 V in CH 2 Cl 2 . The compounds mostly display red fluorescence with large Stokes shifts.
Structural modulation of the photophysical and electronic properties of pyrene-based 3D metal–organic frameworks derived from s-block metals
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D0CE01505A
Abstract: Materials in which charge delocalization and migration can be tuned are critical for electronic applications.
Interaction of copper(II) and palladium(II) with linked 2,2′-dipyridylamine derivatives: Synthetic and structural studies
Publisher: Elsevier BV
Date: 09-2008
Revision of the Phytochemistry of Eremophila sturtii and E. mitchellii
Publisher: American Chemical Society (ACS)
Date: 24-01-2018
DOI: 10.1021/ACS.JNATPROD.7B00616
Abstract: Eremophila sturtii and E. mitchellii are found in the arid and temperate regions of Australia and, because of their similar appearances, are often confused. Previous phytochemical investigations have described mitchellene sesquiterpenes (1-5) reported from E. mitchellii but are here demonstrated to be from E. sturtii. A previous study that described serrulatic acids (16 and 17) from a species reported as E. sturtii actually used E. mitchellii. In addition, two new C-15 modified analogues, mitchellenes F (14) and G (15), were isolated from E. sturtii. The absolute configuration of 14 was determined with the first X-ray structure of a compound with the mitchellene skeleton.
Cover Feature: Norbornadiene‐Based Photoswitches with Exceptional Combination of Solar Spectrum Match and Long‐Term Energy Storage (Chem. Eur. J. 49/2018)
Publisher: Wiley
Date: 17-08-2018
Ruthenium(II) Complexes of New Chelating Indolizino[2,3-b]pyrazine- and Indolizino[2,3-b]quinoxaline-Derived Ligands: Syntheses, Electrochemistry and Absorption Spectroscopy
Publisher: CSIRO Publishing
Date: 2008
DOI: 10.1071/CH08339
Abstract: The highly conjugated chelating ligands 5-(2-pyridyl)indolizino[2,3-b]pyrazine 1, 5-(2-pyridyl)indolizino[2,3-b]quinoxaline 2, and 8,9-dimethyl-5-(2-pyridyl)indolizino[2,3-b]quinoxaline 3 were prepared in one step, with good yields, from di-2-pyridylmethane and 2,3-dichloropyrazine, 2,3-dichloroquinoxaline, and 8,9-dimethyl-2,3-dichloroquinoxaline, respectively. Compounds 1–3 display long-wavelength absorption maxima in the green (1) and yellow (2 and 3) to give intensely coloured red and purple solutions, respectively. Bis(2,2′-bipyridyl)ruthenium(ii) and bis(4,4′-dimethyl-2,2′-bipyridyl)ruthenium(ii) complexes were prepared in moderate to good yields, characterized by NMR spectroscopy and mass spectrometry, and studied by cyclic voltammetry and absorption spectroscopy. Copper(ii) and silver(i) nitrate complexes of the ligands were prepared and complexes [Cu(NO3)2(1)], [Cu(NO3)2(2)]2, and [Ag(NO3)(3)2] were characterized by X-ray crystallography. These structures revealed the planar nature of the ligands and confirmed the proposed chelating mode.
Particle size effects in the kinetic trapping of a structurally-locked form of a flexible MOF
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C6CE00082G
Abstract: Controlling the particle size of a flexible metal–organic framework demonstrates that a 2D to 3D transformation gives a kinetically-trapped, structurally-locked form.
Does functionalisation enhance CO2 uptake in interpenetrated MOFs? An examination of the IRMOF-9 series
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C4CC00700J
Abstract: Simulation and experimental data show that network topology and chemical functionality are crucial parameters for CO 2 adsorption in an interpenetrated MOF.
Endohedrally functionalised porous organic cages
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C6CC04423A
Abstract: The synthesis and characterisation of two novel, endohedrally functionalised porous organic cages are presented.
Ritonavir-boosted darunavir combined with raltegravir or tenofovir–emtricitabine in antiretroviral-naive adults infected with HIV-1: 96 week results from the NEAT001/ANRS143 randomised non-inferiority
Publisher: Elsevier BV
Date: 11-2014
Reprogramming Kinetic Phase Control and Tailoring Pore Environments in CoII and ZnII Metal–Organic Frameworks
Publisher: American Chemical Society (ACS)
Date: 23-09-2014
DOI: 10.1021/CG500978S
Solvent-modified dynamic porosity in chiral 3D kagome frameworks
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C3DT00096F
Abstract: Dynamically porous metal-organic frameworks (MOFs) with a chiral quartz-based structure have been synthesized from the multidentate ligand 2,2'-dihydroxybiphenyl-4,4'-dicarboxylate (H2diol). Compounds [Ni(II)(H2diol)(S)2]·xS (where S = DMF or DEF) show marked changes in 77 K N2 uptake between partially desolvated [Ni(II)(H2diol)(S)2] (only the pore solvent is removed) and fully desolvated [Ni(II)(H2diol)] forms. Furthermore, [Ni(II)(H2diol)(DMF)2] displays additional solvent-dependent porosity through the rotation of DMF molecules attached to the axial coordination sites of the Ni(II) centre. A unique feature of the four coordinate Ni(II) centre in [Ni(II)(H2diol)] is the dynamic response to its chemical environment. Exposure of [Ni(II)(H2diol)] to H2O and MeOH vapour leads to coordination of both axial sites of the Ni centres and to the generation of a solvated framework, whereas exposure to EtOH, DMF, acetone, and MeCN does not lead to any change in metal coordination or structure metrics. MeOH vapour adsorption was able to be tracked by time-dependent magnetometry as the solvated and desolvated structures have different magnetic moments. Solvated and desolvated forms of the MOF show remarkable differences in their thermal expansivities [Ni(II)(H2diol)(DMF)2]·DMF displays marked positive thermal expansion (PTE) in the c-axis, yet near to zero thermal expansion, between 90 and 450 K, is observed for [Ni(II)(H2diol)]. These new MOF architectures demonstrate a dynamic structural and colourimetric response to selected adsorbates via a unique mechanism that involves a reversible change in the coordination environment of the metal centre. These coordination changes are mediated throughout the MOF by rotational mobility about the biaryl bond of the ligand.
Continuous flow synthesis of a carbon-based molecular cage macrocycle via a three-fold homocoupling reaction
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C5CC05181A
Abstract: The facile synthesis of the cage molecule (C 110 H 56 Br 2 ) via a remarkable three-fold homo-coupling macrocyclization reaction using continuous flow methodology is reported.
A thin film opening
Publisher: Springer Science and Business Media LLC
Date: 22-03-2016
DOI: 10.1038/NCHEM.2481
Fused pyrazino[2,3-b]indolizine and indolizino[2,3-b]quinoxaline derivatives; synthesis, structures, and properties
Publisher: Elsevier BV
Date: 12-2011
Emerging applications of metal–organic frameworks
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C6CE01030J
Abstract: Metal–organic frameworks are highly crystalline porous materials which present emerging opportunities in biotechnology, catalysis, microelectronics and photonics.
Synthesis and Complexation of Multiarmed Cycloveratrylene-Type Ligands: Observation of the “Boat” and “Distorted-Cup” Conformations of a Cyclotetraveratrylene Derivative
Publisher: Wiley
Date: 29-04-2008
Abstract: Investigations of a previously reported ligand, hexakis(2-pyridylmethyl)cyclotricatechylene (1), and a new tetrameric bridging ligand, octakis(2-pyridylmethyl)cyclotetracatechylene (2), the latter constructed on a larger cyclotetraveratrylene (CTTV) scaffold, are described. Variable-temperature NMR studies support a "sofa" conformation for 2, akin to studies on the parent compound. The coordination chemistry of 2 and its smaller trimeric homologue have also been investigated with silver(I), copper(II) and palladium(II) salts. An unexpected chelating mode was observed for 1 in the structure of DMF subset[Pd(3)Cl(6)(1)] x DMF, whereby the palladium cations bridge two veratrole subunits rather than chelating within a single subunit. In the structure of [Ag(4)(2)][Co(C(2)B(9)H(11))(2)](4) x 2.8 CH(3)CN x H(2)O, ligand 2 adopts a "boat" conformation, whereas in [Pd(4)Cl(8)(2)] x 4 H(2)O, (1)H NMR spectroscopic studies and calculations indicate that the ligand is present in a previously unobserved "distorted-cup" conformation. This conformation was calculated to be approximately 90 kJ mol(-1) lower in energy than the alternative "sofa" conformation. Thus, coordination-induced conformational control over CTTV derivatives offers new routes to exploit the host-guest chemistry of these compounds.
Fortuitousin vitrocompound degradation produces a tractable hit againstMycobacterium tuberculosisdethiobiotin synthetase: a cautionary tale of what goes in, does not always come out
Publisher: Cold Spring Harbor Laboratory
Date: 27-03-2023
DOI: 10.1101/2023.03.26.531482
Abstract: We previously reported potent ligands and inhibitors of Mycobacterium tuberculosis dethiobiotin synthetase ( Mt DTBS), a promising target for antituberculosis drug development (Schumann et al., ACS Chem Biol. 2021, 16, 2339-2347) here the unconventional origin of the fragment compound they were derived from is described for the first time. Compound 1 (9b-hydroxy-6b,7,8,9,9a,9b-hexahydrocyclopenta[3,4]cyclobuta[1,2-c]chromen-6(6a H )-one), identified by in silico fragment screen, was subsequently shown by surface plasmon resonance to have dose-responsive binding ( K D 0.6 mM). Clear electron density was revealed in the DAPA substrate binding pocket, when 1 was soaked into Mt DTBS crystals, but the density was inconsistent with the structure of 1 . Here we show the lactone of 1 hydrolyses to carboxylic acid 2 under basic conditions, including those of the crystallography soak, with subsequent ring-opening of the component cyclobutane ring to form cyclopentylacetic acid 3 . Crystals soaked directly with authentic 3 produced electron density that matched that of crystals soaked with presumed 1 , confirming the identity of the bound ligand. The synthetic utility of fortuitously formed 3 enabled subsequent compound development into nanomolar inhibitors. Our findings represent an ex le of chemical modification within drug discovery assays and demonstrate the value of high-resolution structural data in the fragment hit validation process. A molecule flagged in an in silico docking screen against Mt DTBS, was inadvertently hydrolysed in the crystal conditions used for hit validation. The resulting fragment-sized molecule bound to the DAPA substrate binding pocket of the target enzyme ( Mt DTBS) with millimolar affinity, as measured by surface plasmon resonance, but was later modified to a highly potent (nanomolar) ligand and promising lead for the development of novel tuberculosis treatments.
New cylindrical peptide assemblies defined by extended parallel β-sheets
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C2OB26637G
Abstract: A new approach to non-covalent peptide-based nanotubular or rod-like structures is presented, whereby the monomeric units are preorganised into a β-strand geometry that templates the formation of an extended and unusual parallel β-sheet rod-like structure. The conformational constraint is introduced by Huisgen cycloaddition to give a triazole-based macrocycle, with the resulting self-assembled structures stabilized by a well-defined series of intermolecular hydrogen bonds.
Fortuitous In Vitro Compound Degradation Produces a Tractable Hit against Mycobacterium tuberculosis Dethiobiotin Synthetase: A Cautionary Tale of What Goes In Does Not Always Come Out
Publisher: American Chemical Society (ACS)
Date: 31-08-2023
Chelation-driven fluorescence deactivation in three alkali earth metal MOFs containing 2,2′-dihydroxybiphenyl-4,4′-dicarboxylate
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C3CE41253A
Control of Structure Topology and Spatial Distribution of Biomacromolecules in Protein@ZIF-8 Biocomposites
Publisher: American Chemical Society (ACS)
Date: 31-01-2018
Biomimetic Synthesis Enables the Structure Revision of Furoerioaustralasine
Publisher: American Chemical Society (ACS)
Date: 11-10-2019
DOI: 10.1021/ACS.ORGLETT.9B03392
Abstract: The structure of furoerioaustralasine, a unique Australian alkaloid, has been revised based on a concise, biomimetic synthesis. The key step is a stereospecific, intramolecular ring opening of an epoxide to form a central dihydrofuran fused to a quinoline ring system.
Influence of nanoscale structuralisation on the catalytic performance of ZIF-8: a cautionary surface catalysis study
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C8CE00746B
Abstract: Nanoscale structuralisation is demonstrated to influence the stability and catalytic properties of zeolitic imidazolate framework-8.
Self-assembled metallo-macrocycle based coordination polymers with unsymmetrical amide ligands
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C1DT10853K
Abstract: A series of metallo-macrocyclic based coordination polymers has been prepared from flexible amide ligands N-6-[(3-pyridylmethylamino)carbonyl]-pyridine-2-carboxylic acid (L1-CH(3)) and N-6-[(4-pyridylmethylamino)carbonyl]-pyridine-2-carboxylic acid (L2-CH(3)). In all but one case, self-assembled dinuclear metallo-macrocyclic units form the basis of the polymeric structures, whereby discrete metal centres, and dinuclear or trinuclear clusters, are linked by the self-assembled macrocycles to give 1D and 2D coordination polymers. In one instance, a 1D coordination polymer is formed in a reaction carried out under ambient conditions when the same reaction is conducted under solvothermal conditions a 2D structure is formed. In all but two of these structures, the polymeric chains and nets are close-packed within the crystals. In the case of a 6,3-connected 2D coordination polymer {[Cd(3)(L2-CH(3))(3)(NO(3))(L2)(CH(3)OH)](NO(3))(2)·12½H(2)O}(n) (9), small oval channels percolate down the a-axis of the unit cell.
‘All twisted up’: a dinuclear helicate with a highly contorted pyridazine bridge
Publisher: Elsevier BV
Date: 02-2003
Network structures of cyclotriveratrylene and its derivatives
Publisher: Royal Society of Chemistry (RSC)
Date: 2005
DOI: 10.1039/B505579B
Some reactions of azides with diynyl-bis(phosphine)ruthenium-cyclopentadienyl complexes
Publisher: Elsevier BV
Date: 11-2015
Protecting-Group-Free Site-Selective Reactions in a Metal–Organic Framework Reaction Vessel
Publisher: American Chemical Society (ACS)
Date: 26-04-2018
DOI: 10.1021/JACS.8B02896
Abstract: Site-selective organic transformations are commonly required in the synthesis of complex molecules. By employing a bespoke metal-organic framework (MOF, 1·[Mn(CO)
Synthesis of a Zinc(II) Imidazolium Dicarboxylate Ligand Metal−Organic Framework (MOF): a Potential Precursor to MOF-Tethered N-Heterocyclic Carbene Compounds
Publisher: American Chemical Society (ACS)
Date: 19-01-2010
DOI: 10.1021/IC9021118
Abstract: Two new isomeric dinitrile ligands containing imidazolium salt cores have been synthesized from cyanoanilines in good yield. These have been converted to the corresponding dicarboxylic acids using hydrobromic acid, or the dicarboxylic acids were synthesized directly from the analogous cyanoaniline starting material in a two-step, one-pot reaction. The crystal structures of three of the four compounds are reported. Two reaction pathways with metals are possible for the dicarboxylic acids, initially giving rise to metal carboxylate based metal-organic frameworks (MOFs) as described in this work or N-heterocyclic carbene (NHC) metal complexes en route to the synthesis of MOFs containing tethered NHC complexes. The reaction of 1,3-bis(4-carboxyphenyl)imidazolium bromide with zinc nitrate in dimethylformamide (DMF) gave a one-dimensional (1D) MOF containing the intact imidazolium salt. The potentially porous structure, formed from close packing of the 1D necklace-type polymers, contains channels occupied by disordered DMF solvate molecules. A formate anion also bridges the zinc secondary building units in the 1D polymer, which has an undulating structure resulting from the U-shaped conformation of the dicarboxylate imidazolium ligand.
Towards microstructured optical fibre sensors: surface analysis of silanised lead silicate glass
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C3TC31414F
Crystal-packing motifs of [Ag4L4]4+ star-burst tetrahedra
Publisher: Royal Society of Chemistry (RSC)
Date: 2006
DOI: 10.1039/B609356F
Solar Energy Storage by Molecular Norbornadiene–Quadricyclane Photoswitches: Polymer Film Devices
Publisher: Wiley
Date: 25-04-2019
Metal-Organic Framework-Based Enzyme Biocomposites
Publisher: American Chemical Society (ACS)
Date: 13-01-2021
Synthesis and Coordination Chemistry of 2-(Di-2-pyridylamino)pyrimidine; Structural Aspects of Spin Crossover in an FeII Complex
Publisher: CSIRO Publishing
Date: 2012
DOI: 10.1071/CH12045
Abstract: 2-(Di-2-pyridylamino)pyrimidine (L), a potentially ditopic tetradentate ligand, was synthesized from commercially available di-2-pyridylamine and 2-chloropyrimidine. Despite being capable of bridging two metal atoms with bidentate chelation of both metal centres, L prefers to chelate or bridge through the more basic pyridyl donors of the di-2-pyridylamine moiety. Mononuclear trans-[Fe(NCS)2(L)2] and [Cu(L)2(H2O)](BF4)2·H2O complexes, and a discrete [Ag2(L)4](PF6)2 metallo-macrocycle, were isolated and structurally characterized by X-ray crystallography. A mononuclear palladium complex [PdCl2(L)]·(solvate), where solvate = 1/2H2O or CH2Cl2, was also readily obtained in 71 % yield. One ex le of the ligand acting as a bis(bidentate) bridging ligand was observed in a dinuclear [(PdCl2)2(L)]·3/4H2O complex that was obtained only in very low yield (~3 %) from the reaction that produced [PdCl2(L)]·1/2H2O. trans-[Fe(NCS)2(L)2] undergoes a temperature-dependent high-spin–low-spin crossover at ~205 K that was observed by X-ray crystallography and magnetic measurements, and attempts were made to understand the structural basis of this process. Despite efforts to isolate ex les of L bridging two iron(ii) centres, only the mononuclear trans-[Fe(NCS)2(L)2] species could be obtained.
Pre-organisation or a hydrogen bonding mismatch: silver(I) diamide ligand coordination polymers versus discrete metallo-macrocyclic assemblies
Publisher: Informa UK Limited
Date: 04-07-2012
Disentangling Disorder in the Three-Dimensional Coordination Network of {Ag 3 [Tris(2-pyridylmethyl)cyclotriguaiacylene] 2 }(PF 6 ) 3
Publisher: American Chemical Society (ACS)
Date: 25-05-2005
DOI: 10.1021/CG050061E
Anion-directed self-assembly of metallosupramolecular coordination polymers of the radialene ligand hexa(2-pyridyl)[3]radialene
Publisher: Elsevier BV
Date: 05-2002
A stable silver-based coordination polymer based on rod-like silver(I) nodes with contiguous Ag-S bonding
Publisher: MDPI AG
Date: 04-10-2020
DOI: 10.3390/MOLECULES25194548
Abstract: Silver(I)-based coordination polymers or metal-organic frameworks (MOFs) display useful antibacterial properties, whereby distinct materials with different bonding can afford control over the release of silver(I) ions. Such silver(I) materials are comprised of discrete secondary building units (SBUs), and typically formed with ligands possessing only soft or borderline donors. We postulated that a linker with four potential donor groups, comprising carboxylate and soft thioether donors, 2,5-bis (allylsulfanyl) benzene dicarboxylic acid (ASBDC), could be used to form stable, highly connected coordination polymers with silver(I). Here, we describe the synthesis of a new material, (Ag2(ASBDC)), which possesses a rod-like metal node-based 3D honeycomb structure, strongly π-stacked linkers, and steric bulk to protect the node. Due to the rod-like metal node and the blocking afforded by the ordered allyl groups, the material displays notable thermal and moisture stability. An interesting structural feature of (Ag2(ASBDC)) is contiguous Ag–S bonding, essentially a helical silver chalcogenide wire, which extends through the structure. These interesting structural features, coupled with the relative ease by which MOFs made with linear dicarboxylate linkers can be reticulated, suggests this may be a structure type worthy of further investigation.
Building blocks for coordination polymers: self-assembled cleft-like and planar discrete metallo-macrocyclic complexes
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C2DT12320G
Abstract: Discrete dinuclear metallo-macrocyclic complexes have been prepared from the flexible amide ligand N-6-[(3-pyridylmethylamino)carbonyl]pyridine-2-carboxylic acid (L1-CH(3)), and its more rigid analogue, N-6-[(3-pyridylamino)carbonyl]pyridine-2-carboxylic acid (L3-CH(3)). With ligands L1-CH(3) and L3-CH(3), discrete dinuclear metallo-macrocyclic complexes with the generic formula [Cu(2)(L1-CH(3))(2)(X)(2)(Y)(2)] (7, X = NO(3) 8, X = Cl, Y = H(2)O 9, X = ClO(4), Y = CH(3)OH) and [Cu(2)(L3-CH(3))(2)(X)(2)(Y)(2)] (10, X = NO(3), Y = H(2)O 11, X = ClO(4), Y = CH(3)OH) are obtained. For complexes 7-9, containing the more flexible link L1-CH(3), these complexes are cleft-shaped and hinged at the methylene spacer, which allows the cleft to widen and contract to accommodate different packing modes in the solid-state. In contrast, the rigid link L3-CH(3) gives near planar metallo-macrocyclic structures. These metallo-macrocyclic compounds may be useful building blocks for coordination polymers.
Synthesis and Applications of Porous Organic Cages
Publisher: The Chemical Society of Japan
Date: 05-05-2015
DOI: 10.1246/CL.150021
Feasibility of mixed matrix membrane gas separations employing porous organic cages
Publisher: American Chemical Society (ACS)
Date: 09-01-2014
DOI: 10.1021/JP4079184
Biomimetic Synthesis of Mitchellenes B–H from the Abundant Biological Precursor 14-Hydroxy-6,12-muuroloadien-15-oic Acid
Publisher: American Chemical Society (ACS)
Date: 11-07-2019
Abstract: A step-economic biomimetic synthesis of mitchellenes B-H found in
Biomimetic Synthetic Studies on the Bruceol Family of Meroterpenoid Natural Products
Publisher: American Chemical Society (ACS)
Date: 18-12-2019
Abstract: A biomimetic approach to total synthesis can offer several benefits, including the development of cascade reactions for the rapid generation of molecular complexity, and guidance in the structure revision of old natural products and the anticipation of new ones. Herein, we describe how a biomimetic synthesis of bruceol, a pentacyclic meroterpenoid, led to the anticipation, isolation, and synthesis of isobruceol. The key step in the synthesis of both bruceol and isobruceol was an intramolecular hetero-Diels-Alder reaction of an
Anion-π interactions of hexaaryl[3]radialenes
Publisher: American Chemical Society (ACS)
Date: 19-07-2012
DOI: 10.1021/JP301464S
Abstract: Coordination polymers and discrete metallo-supramolecular assemblies of hexaaryl[3]radialene compounds exhibit intriguing structures with short anion to π-centroid distances in the solid-state. Furthermore, these [3]radialene compounds display useful photophysical and electrochemical properties that make them ideal as potential platforms for anion receptors. In this study, hexafluoro[3]radialene was optimized to the MP2/aug-cc-pVTZ level of theory, and its complexes with halide anions were optimized to HF/6-31G++(d,p), MP2/6-31G++(d,p), M06-2X/6-31G++(d,p), and M06-2X/6-311G++(d,p) levels of theory. Hexafluoro[3]radialene was shown to have properties (large positive Qzz and areas of positive electrostatic surface potential) comparable to other compounds that show anion-π interactions. The interaction energies of complexes of hexafluoro[3]radialene with halide anions were calculated and found to be favorable and equivalent to those of fluorinated aromatic compounds. A series of synthetically accessible hexaaryl[3]radialenes were optimized to HF/6-31G++(d,p) theory and their complexes with halides optimized to the M06-2X/6-31G++(d,p) level of theory. The calculated properties of the electron-deficient hexaaryl[3]radialenes also show large positive Qzz quadrupole moments and two areas of positive potential at the [3]radialene core and the acidic aryl hydrogen atoms. The interaction energies of the complexes of hexaaryl[3]radialenes and halide anions were found to follow the trend F(-) > Cl(-) ≈ Br(-) and correlate with the electron-deficient nature of the [3]radialene. Close contacts were observed between the anion and the radialene core and the aryl hydrogen atoms, suggesting a combination of anion-π and hydrogen bonding is important. Mass spectrometry was used to experimentally observe the complexes of a number of hexaaryl[3]radialenes with F(-), Cl(-), and Br(-) predicted computationally. Anion-[3]radialene complexes were successfully detected, and the stability of the complexes in tandem MS/MS experiments was found to support the computational results.
Studying manganese carbonyl photochemistry in a permanently porous metal–organic framework
Publisher: Royal Society of Chemistry (RSC)
Date: 2023
DOI: 10.1039/D3SC03553K
Abstract: Photo-liberation of CO from a Mn(diimine)(CO) 3 Br moiety anchored within a permanently porous MOF support is studied. The crystallinity and structural flexibility of the MOF allows crystallographic snapshots of the photolysis products to be obtained.
2,3,7,8,12,13-Hexahydroxy-10,15-dihydro-5 H -tribenzo[ a , d , g ]cyclononene acetone disolvate
Publisher: International Union of Crystallography (IUCr)
Date: 02-03-2007
Utilising hinged ligands in MOF synthesis: a covalent linking strategy for forming 3D MOFs
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C4CE00181H
Abstract: A strategy to covalently connect 2D MOFs by ligand design is reported that yields 3D MOFs topologically-related to the 2D structures without the need for a second ‘pillaring link’.
Templated synthesis of zirconium(iv)-based metal–organic layers (MOLs) with accessible chelating sites
Publisher: Royal Society of Chemistry (RSC)
Date: 2022
DOI: 10.1039/D1CC06443F
Abstract: A two-step templating/delamination strategy can provide access to metal–organic layers with accessible chelating sites poised for quantitative post-synthetic metalation.
Computational identification of organic porous molecular crystals
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C6CE00064A
Hexatriynediyl Chain Spanning Two Cp*(dppe)M Termini (M = Fe, Ru): Evidence for the Dependence of Electronic and Magnetic Couplings on the Relative Orientation of the Termini
Publisher: American Chemical Society (ACS)
Date: 07-05-2014
DOI: 10.1021/OM500328Y
Hetero-bimetallic metal–organic polyhedra
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C5CC08336B
Abstract: Porous metal–organic polyhedra (MOPs), constructed from heterometallic Pd II –M II (M = Cu, Ni, Zn) paddlewheel nodes and 5- tert -butyl-1,3-benzenedicarboxylate organic links, were prepared in which the Pd II ions preferentially line the inner surface of the cage molecules.
Metallo-gels and organo-gels with tripodal cyclotriveratrylene-type and 1,3,5-substituted benzene-type ligands
Publisher: Royal Society of Chemistry (RSC)
Date: 2009
DOI: 10.1039/B819352E
Synthesis and X-ray crystal structure of a bridging trispiran ligand
Publisher: ARKAT USA, Inc.
Date: 24-03-2004
Mixed‐Matrix Membranes
Publisher: Wiley
Date: 07-07-2017
Abstract: Research into extended porous materials such as metal-organic frameworks (MOFs) and porous organic frameworks (POFs), as well as the analogous metal-organic polyhedra (MOPs) and porous organic cages (POCs), has blossomed over the last decade. Given their chemical and structural variability and notable porosity, MOFs have been proposed as adsorbents for industrial gas separations and also as promising filler components for high-performance mixed-matrix membranes (MMMs). Research in this area has focused on enhancing the chemical compatibility of the MOF and polymer phases by judiciously functionalizing the organic linkers of the MOF, modifying the MOF surface chemistry, and, more recently, exploring how particle size, morphology, and distribution enhance separation performance. Other filler materials, including POFs, MOPs, and POCs, are also being explored as additives for MMMs and have shown remarkable anti-aging performance and excellent chemical compatibility with commercially available polymers. This Review briefly outlines the state-of-the-art in MOF-MMM fabrication, and the more recent use of POFs and molecular additives.
X-ray crystallographic insights into post-synthetic metalation products in a metal–organic framework
Publisher: The Royal Society
Date: 13-01-2017
Abstract: Post-synthetic modification of metal–organic frameworks (MOFs) facilitates a strategic transformation of potentially inert frameworks into functionalized materials, tailoring them for specific applications. In particular, the post-synthetic incorporation of transition-metal complexes within MOFs, a process known as ‘metalation’, is a particularly promising avenue towards functionalizing MOFs. Herein, we describe the post-synthetic metalation of a microporous MOF with various transition-metal nitrates. The parent framework, 1 , contains free-nitrogen donor chelation sites, which readily coordinate metal complexes in a single-crystal to single-crystal transformation which, remarkably, can be readily monitored by X-ray crystallography. The presence of an open void surrounding the chelation site in 1 prompted us to investigate the effect of the MOF pore environment on included metal complexes, particularly examining whether void space would induce changes in the coordination sphere of chelated complexes reminiscent of those found in the solution state. To test this hypothesis, we systematically metalated 1 with first-row transition-metal nitrates and elucidated the coordination environment of the respective transition-metal complexes using X-ray crystallography. Comparison of the coordination sphere parameters of coordinated transition-metal complexes in 1 against equivalent solid- and solution-state species suggests that the void space in 1 does not markedly influence the coordination sphere of chelated species but we show notably different post-synthetic metalation outcomes when different solvents are used. This article is part of the themed issue ‘Coordination polymers and metal–organic frameworks: materials by design’.
Bone mineral density and inflammatory and bone biomarkers after darunavir–ritonavir combined with either raltegravir or tenofovir–emtricitabine in antiretroviral-naive adults with HIV-1: a substudy of
Publisher: Elsevier BV
Date: 11-2015
Total Synthesis of Atrachinenins A and B
Publisher: American Chemical Society (ACS)
Date: 12-12-2022
DOI: 10.1021/JACS.2C09978
Total Synthesis of Naphterpin and Marinone Natural Products
Publisher: American Chemical Society (ACS)
Date: 24-09-2019
DOI: 10.1021/ACS.ORGLETT.9B03095
Abstract: A concise and ergent strategy for the synthesis of the naphterpin and marinone meroterpenoid families has been developed. The approach features a succession of pericyclic reactions-an aromatic Claisen rearrangement, a retro-6π-electrocyclization, and two Diels-Alder reactions-which facilitated the first total synthesis of naphterpin itself in five steps from 2,5-dimethoxyphenol, alongside similar syntheses of 7-demethylnaphterpin and debromomarinone. Late-stage oxidation and bromination reactions were also investigated, leading to the first total syntheses of naphterpins B and C and isomarinone.
Enhanced Activity of Enzymes Encapsulated in Hydrophilic Metal-Organic Frameworks
Publisher: American Chemical Society (ACS)
Date: 12-01-2019
DOI: 10.1021/JACS.8B10302
Abstract: Encapsulation of biomacromolecules in metal-organic frameworks (MOFs) can preserve biological functionality in harsh environments. Despite the success of this approach, termed biomimietic mineralization, limited consideration has been given to the chemistry of the MOF coating. Here, we show that enzymes encapsulated within hydrophilic MAF-7 or ZIF-90 retain enzymatic activity upon encapsulation and when exposed to high temperatures, denaturing or proteolytic agents, and organic solvents, whereas hydrophobic ZIF-8 affords inactive catalase and negligible protection to urease.
Investigating the Potential of Flexible and Pre-Organized Tetraamide Ligands to Encapsulate Anions in One-Dimensional Coordination Polymers: Synthesis, Spectroscopic Studies and Crystal Structures
Publisher: MDPI AG
Date: 19-01-2021
Abstract: The synthesis of amide-based molecules, possessing pre-organized structures, has received significant attention due to their potential applications as molecular receptors and as components of nanomaterials. In this study, four extended tetraamide ligands incorporating ethylene and propylene spacers, namely 1,2-bis[N,N′-6-(3-pyridylmethylamido)pyridyl-2-carboxyamido]ethane (L1), 1,2-bis[N,N′-6-(4-pyridylmethylamido)pyridyl-2-carboxyamido]ethane (L2), 1,2-bis[N,N′-6-(3-pyridylmethylamido)pyridyl-2-carboxyamido]propane (L3) and 1,2-bis[N,N′-6-(4-pyridylmethylamido)pyridyl-2-carboxyamido]propane (L4), were successfully synthesized. Further, reaction of L2 and L4, incorporating pendant 4-pyridyl donors as the metal coordinating sites, with cadmium salts, produced two close-packed one-dimensional coordination polymers, {[Cd3(L2)4(H2O)10](NO3)6·12H2O·CH3OH}n and {[Cd(SO4)(L4)(H2O)2]·4H2O·CH3OH}n. X-ray crystallography reveals that the flexible tetraamide ligands fold upon themselves in the coordination polymer structure. As a consequence, the anion pocket in {[Cd(SO4)(L4)(H2O)2]·4H2O·CH3OH}n incorporating the ligand with the propylene spacer was blocked from encapsulating charge-balancing anions, which were involved in bridging the di-cadmium units. Interestingly, a strong interaction between the 2,6-pyridine dicarboxamide moiety with the nitrate anions was found in {[Cd3(L2)4(H2O)10](NO3)6·12H2O·CH3OH}n, showing potential for materials made from these ligands to serve as anion receptors.
Syntheses and studies of flexible amide ligands: a toolkit for studying metallo-supramolecular assemblies for anion binding
Publisher: Elsevier BV
Date: 06-2009
Tris(pyridylmethylamino)cyclotriguaiacylene Cavitands: An Investigation of the Solution and Solid-State Behaviour of Metallo-Supramolecular Cages and Cavitand-Based Coordination Polymers
Publisher: Wiley
Date: 27-03-2006
Abstract: The synthesis of the three isomeric tris(pyridylmethylamino)cyclotriguaiacylene cavitands is reported, along with the crystal structures of the 2- and 4-pyridyl derivatives. The generality of a previously described [Ag(2){tris(3-pyridylmethylamino)cyclotriguaiacylene}(2)](2+) dimeric capsule motif and the [Ag(4){tris(4-pyridylmethylamino)cyclotriguaiacylene}(4)](4+) tetrahedron with several silver salts was confirmed in the solid state and the corresponding solution species were investigated by NMR spectroscopy. Host-guest interactions in these systems have been probed and these interactions are demonstrated to alter and influence the self-assembly outcome of the reaction. Notably, introduction of larger glutaronitrile guest molecules to the [Ag(4)L(4)](4+) tetrahedron system prevents formation of the tetrahedral structure, resulting instead in the formation of a 4.8(2) coordination network in the solid state. In the absence of templating acetonitrile guests in the [Ag(2)(3)(2)](2+) capsule system, formation of a cage-based one-dimensional coordination polymer is observed.
2-D coordination polymers of hexa(4-cyanophenyl)[3]-radialene and silver(I): Anion ···π-interactions and radialene C - H···anion hydrogen bonds in the solid-state interactions of hexaaryl[3]-radialenes with anions
Publisher: American Chemical Society (ACS)
Date: 23-04-2009
DOI: 10.1021/CG9002302
MOF matrix isolation: cooperative conformational mobility enables reliable single crystal transformations
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D0FD00012D
Abstract: Preordering of the linker site and utilising framework flexibility are critical to achieving high levels of metal loading during post-synthetic metalation.
Cross-Coupling of Amide and Amide Derivatives to Umbelliferone Nonaflates: Synthesis of Coumarin Derivatives and Fluorescent Materials
Publisher: American Chemical Society (ACS)
Date: 19-05-2020
Boronate Ester Bullvalenes
Publisher: American Chemical Society (ACS)
Date: 11-02-2020
DOI: 10.1021/JACS.9B12930
Silver(i ) complexation of linked 2,2′-dipyridylamine derivatives. Synthetic, solvent extraction, membrane transport and X-ray structural studies
Publisher: Royal Society of Chemistry (RSC)
Date: 2006
DOI: 10.1039/B609738C
Abstract: Synthesis of the 2,2'-dipyridylamine derivatives di-2-pyridylaminomethylbenzene 1, 1,2-bis(di-2-pyridylaminomethyl)benzene 2, 1,3-bis(di-2-pyridylaminomethyl)benzene 3, 2,6-bis(di-2-pyridylaminomethyl)pyridine 4, 1,4-bis(di-2-pyridylaminomethyl)benzene 5, and 1,3,5-tris(di-2-pyridylaminomethyl)benzene 6 are reported together with the single-crystal X-ray structures of 2, 3, and 5. Reaction of in idual salts of the type AgX (where X = NO(3)(-), PF(6)(-), ClO(4)(-), or BF(4)(-)) with the above ligands has led to the isolation of thirteen Ag(I) complexes, nine of which have also been characterised by X-ray diffraction. In part, the inherent flexibility of the respective ligands has resulted in the adoption of a range of coordination arrangements. A series of liquid-liquid (H(2)O/CHCl(3)) extraction experiments of Ag(I) with varying concentrations of 1-6 in the organic phase have been undertaken, with the counter ion in the aqueous phase being respectively picrate, perchlorate and nitrate. In general, extraction efficiencies for a given ionophore followed the Hofmeister order of picrate > perchlorate > nitrate in each case the tris-dpa derivative 6 acting as the most efficient extractant of the six systems investigated. Competitive seven-metal bulk membrane transport experiments (H(2)O/CHCl(3)/H(2)O) employing the above ligands as the ionophore in the organic phase and equimolar concentrations of Co(II), Ni(II), Zn(II), Cu(II), Cd(II), Pb(II) and Ag(I) in the aqueous source phase were also undertaken, with transport occurring against a pH gradient. Under the conditions employed 1 and 5 yielded negligible transport of any of the metals present in the source phase while sole transport selectivity for Ag(I) was observed for 2-4 and 6.
Capsules and Star-Burst Polyhedra: An [Ag2L2] Capsule and a Tetrahedral [Ag4L4] Metallosupramolecular Prism with Cyclotriveratrylene-Type Ligands
Publisher: Wiley
Date: 30-09-2005
Research Front on Coordination Polymers
Publisher: CSIRO Publishing
Date: 2013
DOI: 10.1071/CH13052
Guest-induced crystal-to-crystal expansion and contraction of a 3-D porous coordination polymer
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C2CC17440E
Abstract: A silver(I) 3-D porous coordination polymer (PCP, 1) with a sodalite topology undergoes a remarkable reversible crystal-to-crystal expansion and contraction upon exposure to different solvents. Notably, complete desolvation of 1 also facilitates a transformation to a non-porous 2-D coordination polymer (2).
Exploring the Use of Structure and Polymer Incorporation to Tune Silver Ion Release and Antibacterial Activity of Silver Coordination Polymers
Publisher: Wiley
Date: 10-08-2018
Complexation and structural studies of a sulfonamide aza-15-crown-5 derivative
Publisher: Elsevier BV
Date: 05-2010
Single-Crystal-to-Single-Crystal Transformations of Metal-Organic-Framework-Supported, Site-Isolated Trigonal-Planar Cu(I) Complexes with Labile Ligands
Publisher: American Chemical Society (ACS)
Date: 23-06-2021
An investigation of the coordination chemistry of the hexadentate ligand di-2-pyridylketone azine; the formation of a discrete tetranuclear complex with silver nitrate
Publisher: Royal Society of Chemistry (RSC)
Date: 2005
DOI: 10.1039/B400879K
Triazolium-Containing Metal–Organic Frameworks: Control of Catenation in 2D Copper(II) Paddlewheel Structures
Publisher: CSIRO Publishing
Date: 2013
DOI: 10.1071/CH12462
Abstract: One approach to exploit metal–organic frameworks (MOFs) as heterogeneous catalyst platforms requires the development of materials containing groups that can be utilised to anchor a catalytic moiety into the links within the structure. Here we report the synthesis of the first integrated triazolium-containing MOF linker and the first MOFs containing linkers of this type. 1,4-Bis(4-benzoic acid)-1-methyl-1H-1,2,3-triazolium chloride, H2L1Me, was synthesised in three steps by a ‘click’ reaction of methyl 4-ethynylbenzoate with methyl 4-azidobenzoate, methylation using methyl triflate, followed by ester hydrolysis in overall 74 % yield. The equivalent neutral triazole precursor, 1,4-bis(4-benzoic acid)-1H-1,2,3-triazole hydrochloride, H2L1(HCl), was also prepared and a comparison of the chemistry with Zn(NO3)2·6H2O and Cu(NO3)2·3H2O is presented. The results support the use of reaction conditions to control interpenetration and provide additional evidence that the charge on structurally similar ligands can drastically alter the types of structures that are accessible due to the requirements for charge balance in the final product.
Isomer Interconversion Studied through Single-Crystal to Single-Crystal Transformations in a Metal–Organic Framework Matrix
Publisher: American Chemical Society (ACS)
Date: 21-08-2019
Mono- and dinuclear ruthenium complexes of bridging ligands incorporating two di-2-pyridylamine motifs: Synthesis, spectroscopy and electrochemistry
Publisher: Elsevier BV
Date: 11-2007
A 3-D diamondoid MOF catalyst based on in situ generated [Cu(L)2] N-heterocyclic carbene (NHC) linkers: hydroboration of CO2
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C4CC04761C
Abstract: A new MOF, [Zn 4 O{Cu( L ) 2 } 2 ], with 14 Å channels lined by in situ generated [Cu( L ) 2 ] N-heterocyclic carbene linkers catalyses the hydroboration of CO 2 .
Silver(I) coordination polymers of the ‘hinged’ pyrazine containing ligand di-2-pyrazinylmethane
Publisher: Informa UK Limited
Date: 26-11-2015
Bioinspired Total Synthesis of Hyperireflexolides A and B
Publisher: American Chemical Society (ACS)
Date: 22-08-2023
Metal–organic framework catalysis
Publisher: Royal Society of Chemistry (RSC)
Date: 2017
DOI: 10.1039/C7CE90106B
Abstract: Welcome to this CrystEngComm themed issue entitled “Metal–organic framework catalysis.”
Discovery of (E)-3-((styrylsulfonyl)methyl)pyridine and (E)-2-((styrylsulfonyl)methyl)pyridine derivatives as anticancer agents: synthesis, structure-activity relationships, and biological activities
Publisher: American Chemical Society (ACS)
Date: 10-03-2014
DOI: 10.1021/JM4019614
Abstract: ON01910.Na is a highly effective anticancer agent that induces mitotic arrest and apoptosis. Clinical studies with ON01910 in cancer patients have shown efficacy along with an impressive safety profile. While ON01910 is highly active against cancer cells, it has a low oral availability and requires continuous intravenous infusion or multiple gram doses to ensure sufficient drug exposure for biological activity in patients. We have identified two novel series of styrylsulfonyl-methylpyridines. Lead compounds 8, 9a, 18 and 19a are highly potent mitotic inhibitors and selectively cytotoxic to cancer cells. Impressively, these compounds possess excellent pharmaceutical properties and two lead drug candidates 9a and 18 demonstrated antitumor activities in animal models.
Interwoven 2-D Coordination Network Prepared from the Molecular Host Tris(isonicotinoyl)cyclotriguaiacylene and Silver(I) Cobalt(III) Bis(dicarbollide)
Publisher: American Chemical Society (ACS)
Date: 05-10-2004
DOI: 10.1021/IC049160S
Abstract: A new 3-fold symmetric molecular host, tris(isonicotinoyl)cyclotriguaiacylene, has been synthesized from cyclotriguaiacylene and isonicotinoyl chloride hydrochloride in 70% yield. Its crystal structure shows dimerization of the host molecules into a capsule-like arrangement. When reacted with Ag[Co(C(2)B(9)H(11))(2)], the host forms a 1-D [ML(2)](n) coordination polymer, which assembles into a 2-D interwoven network through a similar dimerization of the host moieties around acetonitrile guests. Thus, the network structure represents an elegant ex le whereby the solid state structure of the building blocks is echoed in the resulting supramolecular assembly. The 2-D sheets are further stabilized by pi...pi stacking interactions between pyridyl donors of alternate 1-D coordination polymers.
Facile Multistep Synthesis of ZnO-Coated β-NaYF4:Yb/Tm Upconversion Nanoparticles as an Antimicrobial Photodynamic Therapy for Persistent Staphylococcus aureus Small Colony Variants
Publisher: American Chemical Society (ACS)
Date: 23-07-2021
Abstract: Antibacterial treatment strategies using functional nanomaterials, such as photodynamic therapy, are urgently required to combat persistent
UV Emission from Lanthanide-Doped Upconversion Nanoparticles in Super-Resolution Microscopy: Potential for Cellular Damage
Publisher: American Chemical Society (ACS)
Date: 13-04-2023
Capturing snapshots of post-synthetic metallation chemistry in metal-organic frameworks
Publisher: Springer Science and Business Media LLC
Date: 07-09-2014
DOI: 10.1038/NCHEM.2045
Abstract: Post-synthetic metallation is employed strategically to imbue metal-organic frameworks (MOFs) with enhanced performance characteristics. However, obtaining precise structural information for metal-centred reactions that take place within the pores of these materials has remained an elusive goal, because of issues with high symmetry in certain MOFs, lower initial crystallinity for some chemically robust MOFs, and the reduction in crystallinity that can result from carrying out post-synthetic reactions on parent crystals. Here, we report a new three-dimensional MOF possessing pore cavities that are lined with vacant di-pyrazole groups poised for post-synthetic metallation. These metallations occur quantitatively without appreciable loss of crystallinity, thereby enabling examination of the products by single-crystal X-ray diffraction. To illustrate the potential of this platform to garner fundamental insight into metal-catalysed reactions in porous solids we use single-crystal X-ray diffraction studies to structurally elucidate the reaction products of consecutive oxidative addition and methyl migration steps that occur within the pores of the Rh-metallated MOF, 1·[Rh(CO)2][Rh(CO)2Cl2].
Coordination chemistry of di-2-pyridylmethane and related bridging ligands with silver(i), copper(ii), palladium(ii) and zinc(ii)
Publisher: Royal Society of Chemistry (RSC)
Date: 2003
DOI: 10.1039/B309479K
Enamines from the biomass derivative Cyrene and reactions with isocyanates and ketenes
Publisher: Elsevier BV
Date: 10-2023
Understanding the structural landscape of Mn-based MOFs formed with hinged pyrazole carboxylate linkers
Publisher: Royal Society of Chemistry (RSC)
Date: 2023
DOI: 10.1039/D3CE00881A
Ruthenium complexes of hexakis(cyanophenyl)[3]radialenes and their di(cyanophenyl)methane precursors: synthesis, photophysical, and electrochemical properties
Publisher: Informa UK Limited
Date: 18-04-2014
Highly active catalyst for CO2 methanation derived from a metal organic framework template
Publisher: Royal Society of Chemistry (RSC)
Date: 2017
DOI: 10.1039/C7TA00958E
Abstract: MOF-derived nanocatalysts activated under reaction conditions display remarkable activity when compared to several controls.
The Dimeric “Hand-Shake” Motif in Complexes and Metallo-Supramolecular Assemblies of Cyclotriveratrylene-Based Ligands
Publisher: Wiley
Date: 10-11-2008
Abstract: A series of clathrate and metal complexes with cyclotriveratrylene-like molecular host ligands show a similar dimeric homomeric inclusion motif in which a ligand arm of one host is the intra-cavity guest of another and vice versa. This "hand-shake" motif is found in the trinuclear transition metal complex [Cu(3)Cl(6)(1)]CH(3)CN1.5 H(2)O in which 1 is tris(4-[2,2',6',2''-terpyridyl]benzyl)cyclotriguaiacylene in the self-included M(4)L(4) tetrahedral metallo-supramolecular assembly [Ag(4)(2)(4)] (BF(4))(4) in which 2 is tris-(2-quinolylmethyl)cyclotriguaiacylene in the 1D coordination chains [Ag(4)]ReO(4) CH(3)CN and [Ag(5)]SbF(6)3 DMFH(2)O in which 4 is tris(1H-imidazol-1-yl)cyclotriguaiacylene and 5 is tris{4-(2-pyridyl)benzyl}cyclotriguaiacylene and in the acetone clathrate of tris{4-(2-pyridyl)benzyl-amino}cyclotriguaiacylene. Clathrates of ligands 2 and 5 do not show the same dimeric motif, although 2 has an extended homomeric inclusion motif that gives a hexagonal network.
Site-specific metal and ligand substitutions in a microporous Mn2+-based metal–organic framework
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C5DT05023E
Abstract: Mixed-ligand syntheses and post-synthetic metal exchange performed on the Mn 3 L 3 structure type results in site-specific manipulations to the framework structure.
Encapsulation of polyoxometalates within layered metal–organic frameworks with topological and pore control
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C3CE41136B
Synthesis and Coordination Chemistry of Doubly-Tridentate Tripodal Pyridazine and Pyrimidine-Derived Ligands: Structural Interplay Between M2L and M2L2 (M = Ni and Pd) Complexes and Magnetic Propertie
Publisher: CSIRO Publishing
Date: 2009
DOI: 10.1071/CH09244
Abstract: The coordination chemistry of three bridging doubly-tridentate ligands, including the known compound 3,6-bis(di-2-pyridylmethyl)pyridazine (1), which is structurally similar to 1,4-bis(di-2-pyridylmethyl)phthalazine (2), and two pyrimidine-linked compounds 4,6-bis(di-2-pyridylmethyl)pyrimidine (3), and 4,6-bis(di-2-pyridylamino)pyrimidine (4), was investigated with FeII, NiII, and PdII metal salts. Ligands 3 and 4 were synthesized in one-pot reactions from easily obtained starting materials compound 3 was synthesized from di-2-pyridylmethane and 4,6-diiodopyrimidine in 48% yield, while ligand 4 was prepared by reacting di-2-pyridylamine with 4,6-dichloropyrimidine in 27% yield. During the synthesis of 4, an additional compound, 4-chloro-6-(di-2-pyridylamino)pyrimidine (5), with only one tridentate binding site was obtained in 30% yield. Reactions of 1, 3, and 4 with FeII or NiII salts gave two types of complexes, either discrete M2L or M2L2 assemblies. The PdII complexes obtained were also characterized as discrete M2L complexes. The compounds were characterized by a combination of NMR and IR spectroscopy, microanalysis and X-ray crystallography. Noticeable differences in the structures obtained for NiII coordination complexes with the carbon-linked (3) and nitrogen-linked (4) ligands were observed, whereby the nitrogen linker adopted a trigonal planar geometry and prevented tridentate facial coordination of the octahedral metal centres. The magnetic properties of dinuclear FeII complexes of 1 were examined to see if they showed spin-crossover effects, a feature recently observed by others in other dinuclear helicate complexes, but the complexes remained high-spin at all temperatures between 300 and 2 K.
Synthesis of Triple‐Stranded Diruthenium(II) Compounds
Publisher: Wiley
Date: 14-06-2022
Abstract: A series of ligands containing a 1,4‐disubstituted 1,2,3‐triazole unit have been used for the formation of triple‐stranded dinuclear Ru(II) complexes. In contrast to the previously reported complexes of labile metals, the use of inert Ru(II) enabled stereoisomeric mixtures of triple‐stranded diruthenium(II) complexes to be accessed. The chromatographic resolution of the enantiomers of a reported helicate containing a more rigid 1,4‐xylyl spacer was carried out on cellulose. The ligand spacer was modified and as the flexibility increased the production of isomeric mixtures was detected the mesocate and helicate forms were separated when an n ‐propyl spacer was used. This pair of diastereomers was found to exhibit photoconversion, a unique observation for Ru(II) compounds of this type. Partial separation via chromatographic resolution was achieved for compounds containing an n ‐butyl spacer, and the presence of a mesocate/helicate pair confirmed.
Kinetically Controlled Porosity in a Robust Organic Cage Material
Publisher: Wiley
Date: 20-02-2013
Using hinged ligands to target structurally flexible copper(II) MOFs
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C3CE41244J
Building blocks for cyclotriveratrylene-based coordination networks
Publisher: Royal Society of Chemistry (RSC)
Date: 2004
DOI: 10.1039/B407165D
Synthesis and X-ray crystal structures of three copper(II) complexes of 1,4- bis (di-2-pyridylmethyl)phthalazine
Publisher: Informa UK Limited
Date: 07-2008
Palladium-Catalyzed Suzuki-Miyaura, Heck and Hydroarylation Reactions on (-)-Levoglucosenone and Application to the Synthesis of Chiral y-Butyrolactones
Publisher: Wiley
Date: 12-10-2015
Bridging ligands comprising two or more di-2-pyridylmethyl or amine arms: Alternatives to 2,2′-bipyridyl-containing bridging ligands
Publisher: Elsevier BV
Date: 08-2011
Control of framework interpenetration for in situ modified hydroxyl functionalised IRMOFs
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C2CC35565E
Abstract: By intimate control of reaction conditions, phase-pure crystalline porous metal-organic framework materials [Zn(4)O(L)(3)] with interpenetrated and non-interpenetrated structures can be synthesised. Under certain conditions, these reactions occur with concomitant deprotection of masked alcohols located on the organic links which yield accessible 'metal-binding' functional groups within the frameworks.
Protein surface functionalisation as a general strategy for facilitating biomimetic mineralisation of ZIF-8
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C8SC00825F
Abstract: The surface charge and chemistry of a protein determines its ability to facilitate biomimetic mineralisation.
Coordination modulated on-off switching of flexibility in a metal–organic framework
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D1SC04712D
Abstract: Stimuli-responsive metal–organic frameworks (MOFs) exhibit dynamic structural changes upon exposure to external stimuli. Here the coordination geometry of a post-synthetically added metal ion drastically changes the adsorption properties.
Ruthenium(II) Complexes of Multidentate Ligands Derived from Di(2-pyridyl)methane
Publisher: CSIRO Publishing
Date: 2003
DOI: 10.1071/CH03019
Abstract: Bis(2,2′-bipyridyl)ruthenium complexes of the model ligand di(2-pyridyl)methane (1) and its multidentate derivatives 1,1,2,2-tetra(2-pyridyl)ethane (2), tetra(2-pyridyl)ethene (3), and hexa(2-pyridyl)[3]radialene (4) have been prepared and characterized by NMR, visible absorption spectroscopy, electrochemical measurements, and, in two cases, by X-ray crystallography. Complexes of (2) and (3) exist as conformationally rigid species with lower than expected symmetry. Ligands (2) and (3) proved surprisingly resistant to forming dinuclear ruthenium complexes. The two diastereoisomeric dinuclear complexes of (4), Δ Λ/Λ Δ and Δ Δ/Λ Λ (rac), are shown to be locked in conformations of C1 and C2 point-group symmetry, respectively. This represents a rare ex le where the Δ Λ/Λ Δ-dinuclear complex of a achiral, symmetrically bridging ligand is not a meso compound.
Tuning Molecular Solar Thermal Properties by Modification of a Promising Norbornadiene Photoswitch
Publisher: Wiley
Date: 21-03-2019
Isolating reactive metal-based species in Metal–Organic Frameworks – viable strategies and opportunities
Publisher: Royal Society of Chemistry (RSC)
Date: 2020
DOI: 10.1039/D0SC00485E
Abstract: Metal–organic frameworks can be used to stabilise reactive metal-based species, uncover new reactivity, and investigate metal-centred reactions responsible for catalysis.
Bisketene Equivalents as Diels–Alder Dienes
Publisher: American Chemical Society (ACS)
Date: 18-07-2020
DOI: 10.1021/JACS.0C06306
Front Cover: Synthesis of Triple‐Stranded Diruthenium(II) Compounds (Eur. J. Inorg. Chem. 25/2022)
Publisher: Wiley
Date: 27-07-2022
Synthesis and crystal structure of a 2nm long rectangular copper dimetallomacrocycle
Publisher: Informa UK Limited
Date: 12-12-2007
Coordination chemistry of di-2-pyridylamine-based bridging heterocyclic ligands: A structural study of coordination polymers and discrete dinuclear complexes
Publisher: Elsevier BV
Date: 04-2007
AIMs: a new strategy to control physical aging and gas transport in mixed-matrix membranes
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C5TA02286J
Abstract: The effect of controlling interactions between the components in a mixed-matrix membrane at the molecular level has been explored.
Photoinduced Electron Transfer Based Ion Sensing within an Optical Fiber
Publisher: MDPI AG
Date: 11-10-2011
DOI: 10.3390/S111009560
A metal–organic framework supported iridium catalyst for the gas phase hydrogenation of ethylene
Publisher: Royal Society of Chemistry (RSC)
Date: 2020
DOI: 10.1039/D0CC06058E
Abstract: Gas phase hydrogenation of ethylene by a MOF supported Iridium catalyst highlights the role of support and counteranion effects.
Kinetically controlled porosity in a robust organic cage material
Publisher: Wiley
Date: 20-02-2013
Highly Active Gas Phase Organometallic Catalysis Supported Within Metal–Organic Framework Pores
Publisher: American Chemical Society (ACS)
Date: 10-07-2020
DOI: 10.1021/JACS.0C05286
Protein-induced modifications in crystal morphology of a hydrogen-bonded organic framework
Publisher: Royal Society of Chemistry (RSC)
Date: 2023
DOI: 10.1039/D3TA04707E
Influence of the Synthesis and Storage Conditions on the Activity of Candida antarctica Lipase B ZIF-8 Biocomposites
Publisher: American Chemical Society (ACS)
Date: 07-05-2021
Two-Dimensional and Three-Dimensional Coordination Polymers of Hexakis(4-cyanophenyl)[3]radialene: The Role of Stoichiometry and Kinetics
Publisher: American Chemical Society (ACS)
Date: 16-05-2013
DOI: 10.1021/CG400036X
ortho-Quinone Methide Cyclizations Inspired by the Busseihydroquinone Family of Natural Products
Publisher: American Chemical Society (ACS)
Date: 08-10-2019
DOI: 10.1021/ACS.ORGLETT.9B03060
Abstract: A series of cascade reactions of
Synthesis of Guaia-4(5)-en-11-ol, Guaia-5(6)-en-11-ol, Aciphyllene, 1-epi-Melicodenones C and E, and Other Guaiane-Type Sesquiterpenoids via the Diastereoselective Epoxidation of Guaiol
Publisher: American Chemical Society (ACS)
Date: 20-10-2014
DOI: 10.1021/NP500611Z
Abstract: The diastereomeric ratio of epoxidation of the internally bridged carbon-carbon double bond of guaiol (1a) is strongly influenced by the combined effects of the types of remote protecting groups on the hydroxyisopropyl side chain, choice of solvent, and epoxidizing reagent. This observation has allowed us to devise concise stereoselective syntheses of a range of guaiane-type sesquiterpenoids via an epoxidation, ring-opening/elimination, and functionality manipulation sequence. Natural products guaia-4(5)-en-11-ol (2a), guaia-5(6)-en-11-ol (3), and aciphyllene (4a) and epimers of the recently isolated natural products, 1-epi-guaia-4(5)-en-11-ol (2b), 1-epi-aciphyllene (4b), and 1-epi-melicodenones C (5a) and E (6a), were synthesized in good yields in relatively few steps.
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