ORCID Profile
0000-0002-0585-0843
Current Organisation
University of Southampton
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Publisher: Elsevier BV
Date: 03-2006
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C9CC01666J
Abstract: A synthetic approach to chrysophaentin F is described featuring an array of metal catalysed coupling reactions (Cu, Ni, Pd, W, Mo).
Publisher: Royal Society of Chemistry (RSC)
Date: 2008
DOI: 10.1039/B803260B
Publisher: Wiley
Date: 21-04-2005
Publisher: Elsevier BV
Date: 02-2003
Publisher: Royal Society of Chemistry (RSC)
Date: 2006
DOI: 10.1039/B516238F
Publisher: Royal Society of Chemistry (RSC)
Date: 04-02-2003
DOI: 10.1039/B210847J
Abstract: The crystal structures of anion complexes of two nitroaromatic functionalised isophthalamides are reported the structures reveal assembly around anions in the solid-state and in the case of the fluoride complex of receptor 2, the formation of a double helix.
Publisher: Wiley
Date: 04-03-2021
Publisher: American Chemical Society (ACS)
Date: 25-08-2006
DOI: 10.1021/JA064012H
Publisher: Elsevier BV
Date: 07-2001
Publisher: American Chemical Society (ACS)
Date: 22-01-2004
DOI: 10.1021/OM034217O
Publisher: Royal Society of Chemistry (RSC)
Date: 2008
DOI: 10.1039/B802506A
Abstract: Metal complexes of 2,5-dicarboxamidopyrroles and 2,5-dicarbothioamidopyrroles have been structurally characterised for the first time, complementing the significant amount of work that has been reported for the analogous pyridine ligands. N,N'-Bis(3,5-dinitrophenyl)-3,4-diphenyl-1H-pyrrole-2,5-dicarboxamide forms octahedral bis(tridentate) complexes with cobalt(III) and nickel(II), where the ligands are bound to the metal centres through deprotonated pyrrole and amide N atoms. N,N'-Dibutyl-3,4-diphenyl-1H-pyrrole-2,5-dicarboxthioamide and N,N'-diphenyl-3,4-diphenyl-1H-pyrrole-2,5-dicarboxthioamide also form bis(tridentate) cobalt complexes but are only deprotonated at the pyrrole N atom, the remainder of the coordination sphere comprising the thioamide S atoms. The dibutyl derivative was isolated as a Co(II) complex, whereas the diphenyl system deposited a Co(III) complex. In contrast, N,N'-dibutyl-3,4-dichloro-1H-pyrrole-2,5-dicarboxamide was found to act as a bidentate ligand, in an octahedral cobalt(II) complex comprising of two bidentate pyrrole ligands, and two aqua ligands. Synthesis of N,N-bis(pyridin-2-ylmethyl)-3,4-diphenyl-1H-pyrrole-2,5-carboxamide gave a pyrrole ligand with increased denticity. Reaction with cobalt(II) chloride resulted in the isolation of a dinuclear helicate complex. The ligand was found to have undergone addition of a methoxy group to one of the linking methylene carbons, presumably as a result of the oxidative addition of solvent methanol.
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C8SC05155K
Abstract: A series of fluorinated tripodal tris-thioureas function as highly active anion transporters across lipid bilayers and cell membranes.
Publisher: Royal Society of Chemistry (RSC)
Date: 2009
DOI: 10.1039/B912942A
Abstract: The presence of Pt(II) allows pre-organisation of 4,4'-dicarboxamidoindole-2,2'-bipyridine, enhancing anion affinity with the resulting complex displaying selectivity for dihydrogen phosphate in DMSO-d6-0.5% water. Moreover the Pt(II) complex behaves as a colorimetic sensor for fluoride.
Publisher: Informa UK Limited
Date: 03-2007
Publisher: Royal Society of Chemistry (RSC)
Date: 2006
DOI: 10.1039/B610938A
Abstract: A macrocyclic amidourea shows anion dependent binding modes with a variety of different putative anionic guests.
Publisher: Informa UK Limited
Date: 11-11-2011
Publisher: Royal Society of Chemistry (RSC)
Date: 2010
DOI: 10.1039/C0OB00128G
Abstract: Three new bis-1,2,3-triazole strapped calix[4]pyrroles have been prepared via'click' chemistry and their anion complexation and lipid bilayer transport properties studied by a combination of single crystal X-ray diffraction studies, (1)H NMR titration techniques, isothermal titration calorimetry and lipid bilayer anion transport studies in POPC vesicles. Bilayer transport efficiency for transmembrane chloride transport was found to directly depend on the length of the alkyl chain present in the bis-triazole strap.
Publisher: Royal Society of Chemistry (RSC)
Date: 2006
DOI: 10.1039/B511963D
Publisher: International Union of Crystallography (IUCr)
Date: 09-04-2005
Publisher: Royal Society of Chemistry (RSC)
Date: 2007
DOI: 10.1039/B703259E
Publisher: Royal Society of Chemistry (RSC)
Date: 2004
DOI: 10.1039/B409115A
Publisher: Institute of Organic Chemistry & Biochemistry
Date: 2004
DOI: 10.1135/CCCC20041301
Abstract: Thiophene-2,4- and -2,5-biscarboxamides have been synthesised and shown to act as anion receptors in DMSO- d 6 /water solution. The crystal structure of the fluoride complex of a N , N' -diphenylthiophene-2,5-biscarboxamide derivative has been solved and reveals the involvement of the thiophene CH protons in anion complexation in the solid state.
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C3OB41522H
Publisher: Royal Society of Chemistry (RSC)
Date: 2008
DOI: 10.1039/B715125J
Publisher: Informa UK Limited
Date: 02-08-2013
Publisher: Royal Society of Chemistry (RSC)
Date: 2005
DOI: 10.1039/B503906A
Abstract: An amidopyrrole with appended imidazole group can bind and co-transport H+/Cl- across vesicle membranes much more effectively than an analogue with an appended pyridyl group.
Publisher: Royal Society of Chemistry (RSC)
Date: 2010
DOI: 10.1039/C0SC00202J
Publisher: American Chemical Society (ACS)
Date: 29-08-2002
DOI: 10.1021/JA027118V
Abstract: Two molecules containing two 2,5-diamido,3,4-dichloropyrrole units linked via 1,3- or 1,4-substituted benzene rings have been synthesized. The pyrrole groups in these compounds deprotonate in the presence of tetrabutylammonium fluoride and form pyrrole anion dimers via NH...N- hydrogen bonds. This dimerization process results in the formation of polyanionic chains linked via an unusual "orthogonal" hydrogen-bonding array.
Publisher: Royal Society of Chemistry (RSC)
Date: 19-08-2002
DOI: 10.1039/B204295A
Abstract: The propensity of amine, ammonium and amide pendant arm 2,5-diamidopyrrole derivatives to act as anion receptors has been investigated the anion-coordination ability of these species has been determined by 1H NMR titration techniques revealing a marked selectivity of the amine functionalised receptor for hydrogen sulfate anions.
Publisher: Royal Society of Chemistry (RSC)
Date: 2007
DOI: 10.1039/B616467F
Publisher: American Chemical Society (ACS)
Date: 16-08-2011
DOI: 10.1021/JA205884Y
Publisher: American Chemical Society (ACS)
Date: 07-12-2016
DOI: 10.1021/JACS.6B10694
Abstract: Fluoride has been overlooked as a target in the development of synthetic anion transporters despite natural fluoride transport channels being recently discovered. In this paper we report the direct measurement of fluoride transport across lipid bilayers facilitated by a series of strapped calix[4]pyrroles and show that these compounds facilitate transport via an electrogenic mechanism (determined using valinomycin and monensin coupled transport assays and an additional osmotic response assay). An HPTS transport assay was used to quantify this electrogenic process and assess the interference of naturally occurring fatty acids with the transport process and Cl
Publisher: Royal Society of Chemistry (RSC)
Date: 2009
DOI: 10.1039/B904089G
Abstract: A new triazole-strapped calix[4]pyrrole synthesised via'click' chemistry shows high affinity for chloride and lipid bilayer chloride transport properties.
Publisher: Royal Society of Chemistry (RSC)
Date: 2010
DOI: 10.1039/B916113A
Publisher: Royal Society of Chemistry (RSC)
Date: 2003
DOI: 10.1039/B303532H
Publisher: Royal Society of Chemistry (RSC)
Date: 2006
DOI: 10.1039/B600251J
Publisher: American Chemical Society (ACS)
Date: 28-06-2002
DOI: 10.1021/JA025572T
Abstract: A new "super-extended cavity" tetraacetylcalix[4]pyrrole derivative was synthesized and characterized, and X-ray crystal structures of complexes bound to fluoride and acetonitrile were obtained. The binding behavior of this receptor was investigated by NMR titration, and the complex was found to exclusively bind fluoride ions in DMSO-d(6). This unusual binding behavior was investigated by Monte Carlo free energy perturbation simulations and Poisson calculations, and the ion specificity was seen to result from the favorable electrostatic interactions that the fluoride gains by sitting lower in the phenolic cavity of the receptor. The effect of water present in the DMSO on the calculated free energies of binding was also investigated. Owing to the use of a saturated ion solution, the effect of contaminating water is small in this case however, it has the potential to be very significant at lower ion concentrations. Finally, the adaptive umbrella WHAM protocol was investigated and optimized for use in binding free energy calculations, and its efficiency was compared to that of the free energy perturbation calculations adaptive umbrella WHAM was found to be approximately two times more efficient. In addition, structural evidence demonstrates that the protocol explores a wider conformational range than free energy perturbation and should therefore be the method of choice. This paper represents the first complete application of this methodology to "alchemical" changes.
Publisher: American Chemical Society (ACS)
Date: 19-10-2001
DOI: 10.1021/JO016020G
Abstract: Four new 2-amidopyrroles and 2,5-diamidopyrroles have been synthesized and their anion complexation properties investigated. The crystal structures of these receptors have been elucidated and reveal hydrogen bonding in the solid state leading to dimer and network formation. Selectivity for oxo-anions has been demonstrated by (1)H NMR titration techniques.
Publisher: Royal Society of Chemistry (RSC)
Date: 2008
DOI: 10.1039/B806238B
Abstract: Neutral 1,3-di(1H-indol-7-yl)ureas are selective dihydrogen phosphate receptors in polar solvent mixtures (DMSO-d(6)-25% water).
Publisher: Wiley
Date: 04-03-2021
Publisher: American Chemical Society (ACS)
Date: 25-01-2007
DOI: 10.1021/JA068067V
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C3SC51023A
Publisher: Informa UK Limited
Date: 2008
Publisher: Royal Society of Chemistry (RSC)
Date: 12-03-2002
DOI: 10.1039/B200980C
Abstract: 3,4-Dichoro-1H-pyrrole-2,5-dicarboxylic acid bis-phenylamide 3 and 3,4-dichoro-1H-pyrrole-2,5-dicarboxylic acid bis-butylamide 4 have been prepared and shown to deprotonate in the presence of basic anions: the X-ray crystal structure of the tetrabutylammonium salt of 3-H+ reveals the formation of a dimer in the solid state.
Publisher: Royal Society of Chemistry (RSC)
Date: 2005
DOI: 10.1039/B510506D
Abstract: Anion complexation studies on a series of platinum(II) tetrakis(pyrrolylpyridine) salts demonstrate the importance of CH-anion hydrogen bonds in coordinating anionic guests in solution and the solid-state.
Publisher: Informa UK Limited
Date: 2009
Publisher: Wiley
Date: 10-11-2008
Abstract: 1,3-Diindolylureas and thioureas have been synthesised and their anion complexation properties in solution studied. Whilst diindolylthioureas showed only moderate affinities and selectivities, diindolylureas show remarkably high affinity for dihydrogen phosphate in solution for an acyclic, neutral receptor in water/[D(6)]DMSO mixtures. These easy-to-make compounds adopt relatively planar conformations in the solid-state and are able to donate four hydrogen bonds and yet not fill the coordination sphere of carbonate or phosphate, allowing two or three receptors to bind to each anion in the solid-state.
Publisher: International Union of Crystallography (IUCr)
Date: 30-11-2001
Publisher: International Union of Crystallography (IUCr)
Date: 09-04-2005
Publisher: Royal Society of Chemistry (RSC)
Date: 28-01-2003
DOI: 10.1039/B210848H
Abstract: Two new pyrrole 2,5-diamide clefts have been synthesized containing 4-nitrophenyl or 3,5-dinitrophenyl groups appended to the amide positions. The 3,5-dinitrophenyl derivative has been shown to deprotonate in the presence of fluoride, which in acetonitrile solution, gives rise to a deep blue colour.
Publisher: Elsevier BV
Date: 06-2002
Publisher: Royal Society of Chemistry (RSC)
Date: 2006
DOI: 10.1039/B517308F
Abstract: A pyrrolylamidothiourea deprotonates in the presence of one equivalent of not only fluoride, but also acetate, benzoate or dihydrogen phosphate in DMSO solution with structural studies using synchrotron radiation confirming thiourea deprotonation in the solid state.
Publisher: Royal Society of Chemistry (RSC)
Date: 2005
DOI: 10.1039/B513059J
Abstract: The role of solvent (and other species) in the formation of networks from tetrakis(thiourea)platinum(II) cations and croconate anions is examined, with crystallisations from DMSO giving rise to a structure containing solvent filled channels.
Publisher: Informa UK Limited
Date: 10-2004
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C0SC00503G
Publisher: Royal Society of Chemistry (RSC)
Date: 06-01-2014
DOI: 10.1039/C3RA45956J
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C6OB01591C
Abstract: A synthetic analogue of the marine natural product cribrostatin 6 is synthesized that selectively triggers apoptosis in cancer cells via elevation of intracellular ROS.
Publisher: Royal Society of Chemistry (RSC)
Date: 2005
DOI: 10.1039/B511932D
Publisher: Royal Society of Chemistry (RSC)
Date: 2010
DOI: 10.1039/C0CC01684E
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C2OB26299A
Abstract: The influence of anions on tautomerism in benzimidazole containing anion receptors has been studied via a variety of techniques in both solution and the solid state. The results show that hydrogen bonding interactions between the receptors and guests have a significant effect of the nature of the tautomer present. The compounds show a preference for complexation of lactate over pyruvate.
Publisher: World Scientific Pub Co Pte Lt
Date: 2020
DOI: 10.1142/S1088424619501591
Abstract: Synthetic anion receptors that facilitate transmembrane chloride transport are of interest as potential therapeutic agents for cancer and cystic fibrosis. Transporters selective for chloride over protons are desired for therapeutic applications to avoid autophagy inhibition and cytotoxicity. Ex les of such compounds are rare because the majority of anion transporters can interact with the carboxylate head groups of fatty acids leading to proton leakage. In this paper, we report the synthesis, anion binding and transmembrane anion transport properties of two novel bis-triazole-functionalized calixpyrroles with extended straps, and compare them to previously reported shorter-strap analogues known to exhibit high Cl [Formula: see text] H[Formula: see text] selectivity. We demonstrate improved chloride transport activities of the strap-extended compounds that likely benefit from increased lipophilicity, and reduced Cl [Formula: see text] H[Formula: see text] selectivity due to the larger anion binding cavities facilitating interaction with fatty acids. The results are instructive for future design of ideal anion transporters with potent activity and high selectivity against proton leakage.
Publisher: Royal Society of Chemistry (RSC)
Date: 2006
DOI: 10.1039/B612524G
Publisher: Royal Society of Chemistry (RSC)
Date: 2009
DOI: 10.1039/B900178F
Abstract: A series of fluorescent carbazolylurea base anion receptors have been synthesised that show a high affinity for oxo-anions (particularly bicarbonate and acetate). The fluorescence of dicarbazolylurea (1) is quenched upon addition of benzoate anions in DMSO-0.5% water.
Publisher: Royal Society of Chemistry (RSC)
Date: 2007
DOI: 10.1039/B703905K
Abstract: Two cleft-like anion receptors have been synthesised that contain indole hydrogen-bond donors and show fluoride selectively in a DMSO-water solution with crystallographic studies showing a 'twisted' binding mode for fluoride in the solid state.
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C4DT02893G
Abstract: A new family of bis-methylureas have been synthesised and their ability to bind anions both in solution and in the solid state and to transport them through lipid membrane have been studied.
Publisher: Informa UK Limited
Date: 06-2008
Publisher: Informa UK Limited
Date: 27-04-2015
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C2SC21112B
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C3TC00760J
Publisher: Royal Society of Chemistry (RSC)
Date: 31-05-2002
DOI: 10.1039/B202989H
Publisher: Elsevier BV
Date: 03-2002
Publisher: Elsevier BV
Date: 09-2001
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C2CC38198B
Publisher: American Chemical Society (ACS)
Date: 16-10-2007
DOI: 10.1021/JO701702P
Abstract: A series of 2,7-functionalized indoles have been synthesized with appended amide and/or urea or thiourea groups. Anion complexation studies show a marked difference in the mode of interaction of carboxylates with indole-ureas vs indole-amides.
Publisher: American Chemical Society (ACS)
Date: 15-03-2006
DOI: 10.1021/OL060193G
Publisher: Royal Society of Chemistry (RSC)
Date: 2005
DOI: 10.1039/B413654C
Abstract: Steric interactions in 1,3-dicarboxamidoanthraquinones have been employed to 'twist' isophthalamide-like anion binding sites the crystal structure of the fluoride complex of a bis-3,5-dichlorophenylamide derivative shows the receptor acting as a 'hydrogen-bonding corner' in a '2 + 2' fluoride containing molecular box.
Publisher: Wiley
Date: 03-04-2007
Abstract: The anion-binding properties of two similar hybrid amide/urea macrocycles containing either a 2,6-dicarboxamidophenyl or a 2,6-dicarboxamidopyridine group are compared. Significant differences in anion affinity and mode of interaction with anions are attributed to the presence of intramolecular hydrogen bonds in the pyridine system. In fact, remarkably, the phenyl macrocycle undergoes amide hydrolysis under neutral conditions in DMSO/water. The anion binding abilities of the receptors are compared to those of acyclic analogues of the macrocycles that show that the phenyl receptor behaves in a similar fashion to acyclic urea-containing receptors (i.e., showing little selectivity amongst oxo anions), whilst the pyridine-containing receptor shows a high affinity and selectivity for carboxylates.
Publisher: Wiley
Date: 22-02-2010
Abstract: Complexation of dihydrogen phosphate by an anion receptor containing six hydrogen bond donor groups has been shown to reduce the pK(a) of the bound anionic species to such an extent that addition of further aliquots of dihydrogen phosphate result in deprotonation of the bound species with the resultant formation of a monohydrogen phosphate receptor complex. X-ray crystallographic studies confirm monohydrogen phosphate complex formation in the solid state. In this way, this study explains the formation of complexes with unusual stoichiometries when investigating the binding of dihydrogenphosphate anion to hydrogen-bonding receptors.
Publisher: Royal Society of Chemistry (RSC)
Date: 2008
DOI: 10.1039/B713431B
Abstract: Sulfonamide groups, commonly used as neutral hydrogen bond donors in a wide variety of anion receptors, deprotonate upon addition of certain basic anionic guests in two simple functionalised ureas.
Publisher: American Chemical Society (ACS)
Date: 24-06-2016
DOI: 10.1021/JACS.6B04656
Abstract: Gated ion transport across biological membranes is an intrinsic process regulated by protein channels. Synthetic anion carriers (anionophores) have potential applications in biological research however, previously reported ex les are mostly nonspecific, capable of mediating both electrogenic and electroneutral (nonelectrogenic) transport processes. Here we show the transmembrane Cl(-) transport studies of synthetic phenylthiosemicarbazones mimicking the function of acid-sensing (proton-gated) ion channels. These anionophores have remarkable pH-switchable transport properties with up to 640-fold increase in transport efficacy on going from pH 7.2 to 4.0. This "gated" process is triggered by protonation of the imino nitrogen and concomitant conformational change of the anion-binding thiourea moiety from anti to syn. By using a combination of two cationophore-coupled transport assays, with either monensin or valinomycin, we have elucidated the fundamental transport mechanism of phenylthiosemicarbazones which is shown to be nonelectrogenic, inseparable H(+)/Cl(-) cotransport. This study demonstrates the first ex les of pH-switchable nonelectrogenic anion transporters.
Publisher: MDPI AG
Date: 03-09-2019
DOI: 10.3390/MOLECULES24173204
Abstract: Materials that combine flexibility and open metal sites are crucial for myriad applications. In this article, we report a 2D coordination polymer (CP) assembled from CuII ions and a flexible meta-carborane-based linker [Cu2(L1)2(Solv)2]•xSolv (1-DMA, 1-DMF, and 1-MeOH L1: 1,7-di(4-carboxyphenyl)-1,7-dicarba-closo-dodecaborane). 1-DMF undergoes an unusual ex le of reversible phase transition on solvent treatment (i.e., MeOH and CH2Cl2). Solvent exchange, followed by thermal activation provided a new porous phase that exhibits an estimated Brunauer-Emmett-Teller (BET) surface area of 301 m2 g−1 and is capable of a CO2 uptake of 41 cm3 g−1. The transformation is reversible and 1-DMF is reformed on addition of DMF to the porous phase. We provide evidence for the reversible process being the result of the formation/cleavage of weak but attractive B–H∙∙∙Cu interactions by a combination of single-crystal (SCXRD), powder (PXRD) X-ray diffraction, Raman spectroscopy, and DFT calculations.
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C1CC12439K
Abstract: Compounds containing cyanoguanidine and 3-amino-1,2,4-benzothiadiazine-1,1-dioxide have been studied as anion receptors and transporters. Significant affinity for oxo-anions was observed in organic solution and the receptors were found to function as transmembrane chloride/nitrate antiporters with transport rates enhanced in the presence of valinomycin-K(+) complex.
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C1DT10441A
Abstract: The coordination chemistry of 2,5-dicarbothioamidopyrrole ligands, namely N2,N5-dibutyl-3,4-diphenyl-1H-pyrrole-2,5-bis(carbothioamide) and N2,N5,3,4-tetraphenyl-1H-pyrrole-2,5-bis(carbothioamide), has been investigated with Cu(II) metal centres by means of X-ray crystallography. This resulted in the formation of the expected planar S,N,S' coordinated complex for the former ligand and unexpected ring-closure reactions, with formation of benzothiazole sidearms, for the latter. Both Cu(II) and Cu(I), used in large excess, were found to favour the ring-closure reaction, although the structural characterisation of the resulting complexes contained only Cu(II) cations, with varying coordination geometries ranging from square planar and square-based pyramidal to tetrahedral. By repeating the reaction using a slight excess of Cu(II) (2 : 1) two more different structures were obtained where the metal was coordinated to the original ligand, N2,N5,3,4-tetraphenyl-1H-pyrrole-2,5-bis(carbothioamide), or to the mixed ligand where only one of the thioamide substituents had converted to a benzothiazole. The essential role of Cu for the ring closure reaction was also established by comparing its complex with structural features of the analogous Co(II) complex, the latter revealing no ring closure to give benzothiazole substituents and co-crystallisation of a mixed Co(II)/Co(III) complex. Finally, the structure and photophysical properties of the corresponding 3,4-diphenyl-2,5-bis(benzothiozol-5-yl)-pyrrole ligand, obtained via treatment of the thioamide with K(3)[Fe(CN)(6)], were also investigated revealing a blue-centered emission.
Publisher: Wiley
Date: 27-03-2012
Publisher: Royal Society of Chemistry (RSC)
Date: 2006
DOI: 10.1039/B603223K
Publisher: Royal Society of Chemistry (RSC)
Date: 2007
DOI: 10.1039/B618072H
Abstract: The interaction of a variety of acridinone derivatives containing hydrogen-bond donor groups in the 4- and 5-positions with anions demonstrate the potential of this new scaffold in anion receptor and sensor design.
Publisher: Beilstein Institut
Date: 02-09-2011
DOI: 10.3762/BJOC.7.140
Abstract: The conformational properties of 1,3-diindolylureas and thioureas were studied by a combination of heteronuclear NMR spectroscopy and quantum mechanics calculations. NOE experiments showed that the anti–anti conformer along the C7–N7α bonds was predominant in DMSO- d 6 solution in the absence of anions. Anion-induced changes in the 1 H and 15 N chemical shifts confirm the weak binding of chloride anions with negligible conformational changes. Strong deshielding of ureido protons and moderate deshielding of indole NH was observed upon the addition of acetate, benzoate, bicarbonate and dihydrogen phosphate, which indicated that the predominant hydrogen bond interactions occurred at the urea donor groups. Binding of oxo-anions caused conformational changes along the C7–N7α bonds and the syn – syn conformer was preferred for anion–receptor complexes. The conformational changes upon anion binding are in good agreement with energetic preferences established by ab initio calculations.
Publisher: Royal Society of Chemistry (RSC)
Date: 2010
DOI: 10.1039/B917140A
Abstract: The interactions of a series of urea based neutral hydrogen bond donor anion receptors have been investigated with i) alkylcarbamate anions formed by the reaction of carbon dioxide with primary aliphatic amines and ii) the zwitterionic species formed by the reaction of carbon dioxide with 1,4,5,6-tetrahydropyrimidine. Significant downfield chemical shift changes were observed for the urea NH protons in many cases, consistent with host : anion hydrogen bonding interactions, and thus stabilisation of the carbon dioxide bound species. In the case of the alkylammonium-alkylcarbamate salts, this represents successful competition with electrostatic interactions between the alkylcarbamate and alkylammonium components of the salt. A synchrotron structure of a ternary complex formed by an amide appended diindolylurea, the ammonium carbamate salt formed by 1,3-diaminopropane and CO(2) and 18-crown-6, was elucidated and shows the carbamate group bound by six hydrogen bonds (accepting five and donating one) to the functionalised diindolylurea.
Publisher: Royal Society of Chemistry (RSC)
Date: 2005
DOI: 10.1039/B508144K
Abstract: A simple bis-urea containing anion receptor, synthesised from ortho-phenylenediamine, has been shown to have excellent selectivity for carboxylates in solution, with a crystal structure elucidation of the benzoate complex showing four hydrogen bonds between the receptor and anion in the solid state.
Publisher: International Union of Crystallography (IUCr)
Date: 21-04-2006
DOI: 10.1107/S1600536806009135
Abstract: The structure of 2C 16 H 36 N + ·C 8 H 4 O 4 2− ·C 34 H 30 N 8 O 4 , comprises tapes of encapsulated hydrogen-bonded isophthalate anions which are arranged into parallel sheets interleaved with tetrabutylammonium layers each of the two independent neutral molecules is disposed about a centre of inversion.
Publisher: Royal Society of Chemistry (RSC)
Date: 2006
DOI: 10.1039/B604128K
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C1OB06800H
Abstract: Tautomeric switching is observed in a series of benzimidazole-based anion receptors upon addition of basic anions. An N-methylbenzimidazole based receptor selectively interacts with dihydrogen phosphate over a variety of other putative anionic guests via a combination of donated and accepted hydrogen bonds.
Publisher: Informa UK Limited
Date: 07-06-2010
Publisher: Royal Society of Chemistry (RSC)
Date: 2007
DOI: 10.1039/B705854C
Publisher: Royal Society of Chemistry (RSC)
Date: 2008
DOI: 10.1039/B816002C
Abstract: The anion complexation properties of a trans-functionalised platinum(II) complex have been studied revealing a high affinity for sulfate in solution and 3:2 receptor sulfate complex formation in the solid state with the anion bound in a pocket lined with 6 NH and 8 CH hydrogen-bond-donating groups.
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C1MD00068C
Publisher: American Chemical Society (ACS)
Date: 27-04-2020
DOI: 10.1021/JACS.0C01008
Publisher: Elsevier BV
Date: 03-2003
Publisher: International Union of Crystallography (IUCr)
Date: 22-02-2006
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C2CC37468D
Location: United Kingdom of Great Britain and Northern Ireland
Location: United Kingdom of Great Britain and Northern Ireland
Location: United Kingdom of Great Britain and Northern Ireland
No related grants have been discovered for Mark Light.