ORCID Profile
0000-0002-5441-6437
Current Organisation
Deakin University - Geelong Campus at Waurn Ponds
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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)
Analytical Chemistry | Analytical Spectrometry | Organometallic Chemistry | Other Chemical Sciences | Organic Chemistry | Medicinal and Biomolecular Chemistry | Biomolecular Modelling and Design | Physical Chemistry not elsewhere classified | Analytical Chemistry Not Elsewhere Classified | Organic Chemical Synthesis | Biologically Active Molecules | Flow Analysis | Nanochemistry and Supramolecular Chemistry | Physical Organic Chemistry | Analytical Biochemistry | Cell Metabolism
ANZSRC Socio-Economic Objective (SEO)
Expanding Knowledge in the Chemical Sciences | Law enforcement | Scientific Instruments | Expanding Knowledge in the Biological Sciences | Endocrine organs and diseases (incl. diabetes) |
Related Links
Publications
Synthesis and evaluation of cationic norbornanes as peptidomimetic antibacterial agents
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C5OB00621J
Abstract: A family of structurally hiphilic norbornanes has been constructed several of which possess broad spectrum antibacterial activity.
Synthesis, polymerization and wool coating studies of 3-iso-butylpyrrole and 3-iso-pentylpyrrole
Publisher: Elsevier BV
Date: 12-2006
A one-pot, three-component approach to functionalised tetrahydroisoquinolines using domino Heck-aza-Michael reactions
Publisher: Wiley
Date: 08-02-2011
Dual responsive chemosensors for anions: The combination of fluorescent PET (Photoinduced Electron Transfer) and colorimetric chemosensors in a single molecule
Publisher: Elsevier BV
Date: 08-2003
The Influence of the Framework: An Anion‐Binding Study Using Fused [n]Polynorbornanes
Publisher: Wiley
Date: 13-02-2014
Abstract: A series of bis-thiourea-functionalized [n]polynorbornane hosts (1-6) with increasing size were synthesized and their anion-binding properties were evaluated by using ¹H NMR spectroscopic titration and Job’s plot analysis. The larger bis-thiourea-[3]polynorbornane scaffolds 4 and 5 bound acetate in a 1:1 (cooperative) arrangement, whereas the corresponding smaller norbornane host 2, identical in preorganization, bound acetate in a 1:2 (independent) arrangement. In contrast, the size of the framework had no influence on the binding of dihydrogenphosphate. These results clearly highlight the subtle influence that the framework itself can have on host-guest interactions.
Characterisation of lipase fatty acid selectivity using novel omega-3 pNP-acyl esters
Publisher: No publisher found
Date: 2014
Norbornene chaotropic salts as low molecular mass ionic organogelators (LMIOGs)
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C8SC01798K
Abstract: A humble norbornene functions as an ionic organogelator, forms aqueous biphasic and triphasic systems and assembles to form chiral helices.
Colorimetric semi-quantitative measurement of pyrophosphate by functionalised SPPS resin in biological media
Publisher: Elsevier BV
Date: 05-2017
Indole as a scaffold for anion recognition
Publisher: Royal Society of Chemistry (RSC)
Date: 2007
DOI: 10.1039/B702804K
Abstract: Indole has an acidic N-H that can be used to form hydrogen bonds to anions and in this paper the synthesis of three new suitably functionalised indole based anion receptors is presented along with their evaluation using (1)H NMR titration techniques.
Direct Amidation to Access 3-Amido-1,8-Naphthalimides Including Fluorescent Scriptaid Analogues as HDAC Inhibitors
Publisher: MDPI AG
Date: 15-06-2021
Abstract: Methodology to access fluorescent 3-amido-1,8-naphthalimides using direct Buchwald–Hartwig amidation is described. The protocol was successfully used to couple a number of substrates (including an alkylamide, an arylamide, a lactam and a carbamate) to 3-bromo-1,8-naphthalimide in good yield. To further exemplify the approach, a set of scriptaid analogues with amide substituents at the 3-position were prepared. The new compounds were more potent than scriptaid at a number of histone deacetylase (HDAC) isoforms including HDAC6. Activity was further confirmed in a whole cell tubulin deacetylation assay where the inhibitors were more active than the established HDAC6 selective inhibitor Tubastatin. The optical properties of these new, highly active, compounds make them amenable to cellular imaging studies and theranostic applications.
Conductive poly(α,ω-bis(3-pyrrolyl)alkanes)-coated wool fabrics
Publisher: Elsevier BV
Date: 07-2007
Evaluation of tris(4,7-diphenyl-1,10-phenanthrolinedisulfonate)ruthenium(II) as a chemiluminescence reagent
Publisher: Elsevier BV
Date: 02-2009
DOI: 10.1016/J.ACA.2008.12.030
Abstract: Previous studies have suggested that tris(4,7-diphenyl-1,10-phenanthrolinedisulfonate)ruthenium(II) (Ru(BPS)(3)(4-)) has great potential as a chemiluminescence reagent in acidic aqueous solution. We have evaluated four different s les of this reagent (two commercially available and two synthesised in our laboratory) in comparison with tris(2,2'-bipyridine)ruthenium(II) (Ru(bipy)(3)(2+)) and tris(1,10-phenanthroline)ruthenium(II) (Ru(phen)(3)(2+)), using a range of structurally erse analytes. In general, Ru(BPS)(3)(4-) produced more intense chemiluminescence, but the oxidised Ru(BPS)(3)(3-) species is less stable in aqueous solution than Ru(bipy)(3)(3+) and produced a greater blank signal than Ru(bipy)(3)(3+) or Ru(phen)(3)(3+), which had a detrimental effect on sensitivity. Although the complex is often depicted with the sulfonate groups of the BPS ligand in the para position on the phenyl rings, NMR characterisation revealed that the commercially available BPS material used in this study was predominantly the meta isomer.
Application of soluble poly(3-alkylpyrrole) polymers on textiles
Publisher: Elsevier BV
Date: 04-2006
Bis-thiourea macrocycles incorporating fused [n]polynorbornanes: binding of flexible versus rigid dicarboxylates
Publisher: Informa UK Limited
Date: 18-11-2013
Using steric bulk for selective recognition; Blocking the binding site to differentiate guests
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C6CC04549A
Abstract: Amenable to bendable: blocking the binding cleft enhances selectivity for flexible guests.
Accessing highly-halogenated flavanones using protic ionic liquids and microwave irradiation
Publisher: Bentham Science Publishers Ltd.
Date: 2012
Improved synthesis and structural reassignment of MC1568: A class IIa selective HDAC inhibitor
Publisher: American Chemical Society (ACS)
Date: 30-01-2014
DOI: 10.1021/JM401945K
Abstract: An improved synthesis and structural reassignment of the class IIa selective histone deacetylase (HDAC) inhibitor MC1568 are described.
A fluorescent naphthalimide NADH mimic for continuous and reversible sensing of cellular redox state
Publisher: Royal Society of Chemistry (RSC)
Date: 2020
DOI: 10.1039/C9CC09748A
Abstract: A new naphthalimide based NADH mimic that functions as a fully reversible fluorescent “on off” probe for redox state has been synthesised and evaluated.
Luminescent probes for the bioimaging of small anionic species in vitro and in vivo
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C4CS00372A
Abstract: This comprehensive review examines recent developments in the use of fluorescent/luminescent probes for the bioimaging of anionic species. Images in cover art reproduced with permission from ref. 290 and 306.
Synthesis of norbornane bisether antibiotics via silver-mediated alkylation
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C5RA03321G
Abstract: Structurally hiphilic norbornane bisether diguanidines show activity against a range of Gram-positive and Gram-negative bacterial species.
Norbornene-based anion receptors as D -alanine binders
Publisher: Informa UK Limited
Date: 15-10-2015
Coassembled nanostructured bioscaffold reduces the expression of proinflammatory cytokines to induce apoptosis in epithelial cancer cells
Publisher: Elsevier BV
Date: 07-2016
DOI: 10.1016/J.NANO.2016.01.009
Abstract: The local inflammatory environment of the cell promotes the growth of epithelial cancers. Therefore, controlling inflammation locally using a material in a sustained, non-steroidal fashion can effectively kill malignant cells without significant damage to surrounding healthy cells. A promising class of materials for such applications is the nanostructured scaffolds formed by epitope presenting minimalist self-assembled peptides these are bioactive on a cellular length scale, while presenting as an easily handled hydrogel. Here, we show that the assembly process can distribute an anti-inflammatory polysaccharide, fucoidan, localized to the nanofibers within the scaffold to create a biomaterial for cancer therapy. We show that it supports healthy cells, while inducing apoptosis in cancerous epithelial cells, as demonstrated by the significant down-regulation of gene and protein expression pathways associated with epithelial cancer progression. Our findings highlight an innovative material approach with potential applications in local epithelial cancer immunotherapy and drug delivery.
Anion recognition using preorganized thiourea functionalized [3]polynorbornane receptors
Publisher: American Chemical Society (ACS)
Date: 11-2005
DOI: 10.1021/OL051497Q
Abstract: [structure: see text] A new family of [3]polynorbornane frameworks exhibiting conformationally preorganized aromatic thiourea (cleft-like) receptors have been designed and synthesized for anion recognition. These show excellent affinity for the biologically relevant dihydrogenphosphate (H(2)PO(4)(-)) and dihydrogenpyrophosphate (H(2)P(2)O(7)(2)(-)) anions (among others), which are bound in 1:1 and 2:1 (host:anion) ratio, respectively. Moreover, visually striking color changes accompany guest binding, enabling this family to act as colorimetric anion sensors.
Demonstration of bidirectional photoinduced electron transfer (PET) sensing in 4-amino-1,8-naphthalimide based thiourea anion sensors
Publisher: Royal Society of Chemistry (RSC)
Date: 2009
DOI: 10.1039/B907037K
Abstract: The thiourea based 4-amino-1,8-naphthalimide molecules 1-5 were designed as fluorescent anion sensors and their photophysical properties investigated upon recognition of biologically relevant anions such as acetate, dihydrogen phosphate and fluoride in DMSO. Synthesised in a single step from their respective aniline precursors, 6-9, these molecules were designed on the fluorophore-spacer-receptor principle, where in the case of sensors 1-3 the thiourea anion recognition moieties were connected to the fluorophore via the 4-amino moiety, while sensors 4 and 5 had the thiourea moieties connected to the 'imide' via a CH2 spacer. The current study showed that 1-5 operated as photoinduced electron transfer (PET) sensors, as no significant changes were observed in their absorption spectra, while their fluorescence emissions were quenched upon recognition of ions such as AcO(-), H2PO4(-) and F(-), which demonstrates that bidirectional PET sensing occurs in such naphthalimide based anion sensors.
Determining binding constants from 1H NMR titration data using global and local methods: A case study using [ n ]polynorbornane-based anion hosts
Publisher: Informa UK Limited
Date: 29-06-2012
Comparison of homoleptic and heteroleptic 2,2′-bipyridine and 1,10-phenanthroline ruthenium complexes as chemiluminescence and electrochemiluminescence reagents in aqueous solution
Publisher: Elsevier BV
Date: 03-2009
DOI: 10.1016/J.ACA.2008.12.042
Abstract: We have conducted a comprehensive comparative study of Ru(bipy)(3)(2+), Ru(bipy)(2)(phen)(2+), Ru(bipy)(phen)(2)(2+), and Ru(phen)(3)(2+) as chemiluminescence and electrochemiluminescence (ECL) reagents, to address several previous conflicting observations and gain a greater insight into their potential for chemical analysis. Clear trends were observed in many of their spectroscopic and electrochemical properties, but the relative chemiluminescence or ECL intensity with a range of analytes/co-reactants is complicated by the contribution of numerous (sometimes opposing) factors. Significantly, the reversibility of cyclic voltammetric responses for the complexes decreased as the number of phenanthroline ligands was increased, due to the lower stability of their ruthenium(III) form in the aqueous solvent. This trend was also evident over a longer timescale when the ruthenium(III) form was spectrophotometrically monitored after chemical oxidation of the ruthenium(II) complexes. In general, the greater stability of Ru(bipy)(3)(3+) resulted in lower blank signals, although this effect was less pronounced with ECL, where the reagent is oxidised in the presence of the co-reactants. Nevertheless, this shows the need to compare signal-to-blank ratios or detection limits, rather than the more common comparisons of overall signal intensity for different ruthenium complexes. Furthermore, our results support previous observations that, compared to Ru(bipy)(3)(2+), Ru(phen)(3)(2+) provides greater ECL and chemiluminescence intensities with oxalate, which in some circumstances translates to superior detection limits, but they do not support the subsequent generalised notion that Ru(phen)(3)(2+) is a more sensitive reagent than Ru(bipy)(3)(2+) for all analytes.
Simple naphthalimide based anion sensors: Deprotonation induced colour changes and CO2 fixation
Publisher: Elsevier BV
Date: 12-2003
Binding of the terephthalate dianion by di- tri- and tetrathiourea functionalised fused [3] and [5]polynorbornane based hosts
Publisher: Royal Society of Chemistry (RSC)
Date: 2009
DOI: 10.1039/B910522K
Abstract: The affinity of new di-, tri- and tetrathiourea functionalised fused [3] and [5]polynorbornane based hosts 1-6 towards terephthalate2- was proportional to the size of the preorganised cleft/cavity imparted by the polynorbornane scaffold. Receptors based on the [5]polynobornane framework had greater affinities for the anion due to a higher degree of host:guest size complementarity. Hosts 1-5 formed 1:1 host:guest complexes with the rigid dianion, yet remarkably, host 6 was found to bind two terephthalate guests.
Strategies and methods for the attachment of amino acids and peptides to chiral [n]polynorbornane templates
Publisher: Royal Society of Chemistry (RSC)
Date: 2003
DOI: 10.1039/B301980B
Abstract: A versatile synthesis of amino acid and peptide functionalised [n]polynorbornane scaffolds is described. The frameworks are constructed using the stereoselective and regioselective cycloaddition of suitably functionalised chiral cyclobutene epoxides with similar norbornenes. The strategies employed allow a range of topologies to be accessed and a number of regioselectively addressable linkage points to be accommodated.
Direct Observation of Amide Bond Formation in a Plasmonic Nanocavity Triggered by Single Nanoparticle Collisions
Publisher: American Chemical Society (ACS)
Date: 24-06-2021
DOI: 10.1021/JACS.1C02426
Disruption of the Class IIa HDAC Corepressor Complex Increases Energy Expenditure and Lipid Oxidation
Publisher: Elsevier BV
Date: 09-2016
DOI: 10.1016/J.CELREP.2016.08.005
Abstract: Drugs that recapitulate aspects of the exercise adaptive response have the potential to provide better treatment for diseases associated with physical inactivity. We previously observed reduced skeletal muscle class IIa HDAC (histone deacetylase) transcriptional repressive activity during exercise. Here, we find that exercise-like adaptations are induced by skeletal muscle expression of class IIa HDAC mutants that cannot form a corepressor complex. Adaptations include increased metabolic gene expression, mitochondrial capacity, and lipid oxidation. An existing HDAC inhibitor, Scriptaid, had similar phenotypic effects through disruption of the class IIa HDAC corepressor complex. Acute Scriptaid administration to mice increased the expression of metabolic genes, which required an intact class IIa HDAC corepressor complex. Chronic Scriptaid administration increased exercise capacity, whole-body energy expenditure and lipid oxidation, and reduced fasting blood lipids and glucose. Therefore, compounds that disrupt class IIa HDAC function could be used to enhance metabolic health in chronic diseases driven by physical inactivity.
Modular Synthesis of Linear Bis‐ and Tris‐monodentate Fused [6]Polynorbornane‐Based Ligands and their Assembly into Coordination Cages
Publisher: Wiley
Date: 07-01-2015
Abstract: A modular approach has been developed for the synthesis of rigid linear di- and tritopic ligands based on a fused [6]polynorbornane scaffold. The design provides up to three sites for installing functionality, including both "ends" and a "central" position with the advantage that each region can be independently addressed during synthesis. To illustrate the utility of the approach, both pyridyl and picolyl units were incorporated to provide six new ligands, with centers and ends either matched or mismatched. Indeed, both [M2L4] cages with endohedral functionality and [M3L4] complexes were cleanly produced from these ligands with assembled structures confirmed by using (1)H NMR spectroscopy, HRMS, and molecular modelling.
Use of Mg-Al Nanoclay as an Efficient Vehicle for the Delivery of the Herbicide 2,4-Dichlorophenoxyacetic Acid
Publisher: American Chemical Society (ACS)
Date: 22-05-2019
Synthesis and polymerisation of α,ω-bis(3-pyrrolyl)alkanes
Publisher: Elsevier BV
Date: 05-2007
Molecular Recognition of DNA by Rigid [n]-Polynorbornane-Derived Bifunctional Intercalators: Synthesis and Evaluation of Their Binding Properties
Publisher: American Chemical Society (ACS)
Date: 13-04-2007
DOI: 10.1021/JM0613020
Abstract: We have exploited the concept of multivalency in the context of DNA recognition, using novel chemistry to synthesize a new type of bis-intercalator with unusual sequence-selectivity. Bis-intercalation has been observed previously, but design principles for de novo construction of such molecules are not known. Our compounds feature two aromatic moieties projecting from a rigid, polynorbornane-based scaffold. The length and character of the backbone as well as the identity of the intercalators were varied, resulting in mono- or alent recognition of the double helix with varying affinity. Our lead compound proved to be a moderately sequence-selective bis-intercalator with an unwinding angle of 27 degrees and a binding constant of about 8 microM. 9-aminoacridine rings were preferred over acridine carboxamides or naphthalimides, and a rigid [3]-polynorbornane scaffold was superior to a [5]-polynorbornane. The flexibility of the linker connecting the rings to the scaffold, although less influential, could affect the strength and character of the DNA binding.
Size matters - Strong binding of the terephthalate dianion by thiourea functionalised fused [n]polynorbornane hosts
Publisher: Royal Society of Chemistry (RSC)
Date: 2008
DOI: 10.1039/B801798K
Abstract: Remarkably strong binding of the new [5]polynorbornane based host to the terephthalate dianion is based on size complementarity of the preorganised binding cleft with the rigid dicarboxylate guest.
Modular synthesis of 4-aminocarbonyl substituted 1,8-naphthalimides and application in single molecule fluorescence detection
Publisher: Royal Society of Chemistry (RSC)
Date: 2017
DOI: 10.1039/C7CC07922B
Abstract: Robust 1,8-naphthalimide cross-coupling methodology unlocks access to derivatives with interesting photophysical properties and erse applications.
Norbornane-based cationic antimicrobial peptidomimetics targeting the bacterial membrane
Publisher: Elsevier BV
Date: 12-2018
Extraction, identification and detection of synthetic cannabinoids found pre-ban in herbal products in Victoria, Australia
Publisher: Elsevier BV
Date: 03-2018
Scaffold diversity for enhanced activity of glycosylated inhibitors of fungal adhesion
Publisher: Royal Society of Chemistry (RSC)
Date: 2020
DOI: 10.1039/D0MD00224K
Abstract: Norbornene scaffolds are suitable replacements of aromatic cores in glycosylated inhibitors of adhesion of fungal pathogen Candida albicans to epithelial cells.
A general approach to N-heterocyclic scaffolds using domino Heck-aza-Michael reactions
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C0OB00835D
Abstract: Palladium-catalyzed domino Heck-aza-Michael reactions for the synthesis of a series of C1-substituted tetrahydro-β-carbolines, tetrahydroisoquinolines and isoindolines are described. The domino process involves the initial intermolecular Heck reaction of an aryl bromide with an electron deficient alkene, followed by an intramolecular aza-Michael reaction to form the new N-heterocycle in high yield.
Fluorescent anion sensors based on 4-amino-1,8-naphthalimide that employ the 4-amino N-H
Publisher: Elsevier BV
Date: 07-2006
On the use of ‘shortcuts’ in the method of continuous variation (Job's method)
Publisher: Informa UK Limited
Date: 30-04-2014
Rapid synthesis of cyclobutene diesters using a microwave-accelerated ruthenium-catalysed [2+2] cycloaddition
Publisher: Elsevier BV
Date: 11-2010
Rapid formation of diphenylmethyl ethers and thioethers using microwave irradiation and protic ionic liquids
Publisher: Elsevier BV
Date: 04-2012
4-Hydroxy-N-propyl-1,8-naphthalimide esters: New fluorescence-based assay for analysing lipase and esterase activity
Publisher: Elsevier BV
Date: 09-2016
DOI: 10.1016/J.BIOCHI.2016.07.016
Abstract: Research using 1,8-naphthalimide derivatives has expanded rapidly in recent years owing to their cell-permeable nature, ability to target certain cellular locations and fluorescent properties. Here we describe the synthesis of three new esters of 4-hydroxy-N-propyl-1,8-naphthalimide (NAP) and the development of a simple and sensitive assay protocol to measure the activity of carboxylester hydrolases. The NAP fluorophore was esterified with short (butyrate), medium (octanoate) and long (palmitate) chain fatty acids. The esters were spectroscopically characterised and their properties investigated for their suitability as assay substrates. The esters were found to be relatively stable under the conditions of the assay and levels of spontaneous hydrolysis were negligible. Non-specific hydrolysis by proteins such as bovine serum albumin was also minimal. A simple and rapid assay methodology was developed and used to analyse a range of commercially available enzymes that included enzymes defined as lipases, esterases and phospholipases. Clear differences were observed between the enzyme classes with respect to the hydrolysis of the various chain length esters, with lipases preferentially hydrolysing the medium chain ester, whereas esterases reacted more favourably with the short ester. The assay was found to be highly sensitive with the fluorophore detectable to the low nM range. These esters provide alternate substrates from established coumarin-based fluorophores, possessing distinctly different excitation (447 nm) and emission (555 nm) optima. Absorbing at 440-450 nm also offers the flexibility of analysis by UV-visible spectrophotometry. This represents the first instance of a naphthalimide-derived compound being used to analyse these enzymes.
Rapid domino [3+2] cycloaddition, [4+2] cycloreversion, ring-opening and aromatisation of a fused oxanorbornane substrate
Publisher: Elsevier BV
Date: 05-2015
Synthesis of 2-(Benzylthio)-4-(trifluoromethyl)thiazole-5-carboxylates Using S -Benzylisothiouronium Halides as Thiol Equivalents
Publisher: Georg Thieme Verlag KG
Date: 21-05-2015
Solid-state NMR as a probe of anion binding: Molecular dynamics and associations in a [5]polynorbornane bisurea host complexed with terephthalate
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C5CP03628C
Abstract: A suite of solid-state NMR experiments is used to study a supramolecular complex consisting of a [5]polynorbornane bisurea host and terephthalate dianion guest, revealing information on the dynamics of both the host and guest species.
Anion recognition and sensing in organic and aqueous media using luminescent and colorimetric sensors
Publisher: Elsevier BV
Date: 12-2006
Comparing the anion binding of 4-amido- with 4-amino-1,8-naphthalimides
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D1OB01664D
Abstract: The synthesis and evaluation of a new anion receptor based on the 4-amido-1,8-naphthalimide scaffold is described.
Mixed alkoxy/hydroxy 1,8-naphthalimides: expanded fluorescence colour palette andin vitrobioactivity
Publisher: Royal Society of Chemistry (RSC)
Date: 2020
DOI: 10.1039/D0CC01251C
Abstract: An efficient and functional group tolerant route to access hydroxy 1,8-naphthalimides has been used to synthesise a range of mono- and disubstituted hydroxy-1,8-naphthalimides with fluorescence emissions covering the visible spectrum.
Synthesis of 4-amino substituted 1,8-naphthalimide derivatives using palladium-mediated amination
Publisher: Elsevier BV
Date: 10-2014
Soluble poly-3-alkylpyrrole polymers on films and fabrics
Publisher: Elsevier BV
Date: 10-2005
Simultaneous control of spectroscopic and electrochemical properties in functionalised electrochemiluminescent tris(2,2′-bipyridine)ruthenium(ii) complexes
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C0AN00952K
Abstract: Using a combination of electrochemical, spectroscopic and computational techniques, we have explored the fundamental properties of a series of ruthenium diimine complexes designed for coupling with other molecules or surfaces for electrochemiluminescence (ECL) sensing applications. With appropriate choice of ligand functionality, it is possible to manipulate emission wavelengths while keeping the redox ability of the complex relatively constant. DFT calculations show that in the case of electron withdrawing substituents such as ester or amide, the excited state is located on the substituted bipyridine ligand whereas in the case of alkyl functionality it is localised on a bipyridine. The factors that dictate annihilation ECL efficiency are interrelated. For ex le, the same factors that determine ΔG for the annihilation reaction (i.e. the relative energies of the HOMO and LUMO) have a corresponding effect on the energy of the excited state product. As a result, most of the complexes populate the excited state with an efficiency (Φ(ex)) of close to 80% despite the relatively wide range of emission maxima. The quantum yield of emission (Φ(p)) and the possibility of competing side reactions are found to be the main determinants of ECL intensity.
Flexible “Arms” and Anion Recognition
Publisher: Wiley
Date: 12-06-2017
Chemiluminescence detection of opium poppy (Papaver somniferum) alkaloids
Publisher: Elsevier BV
Date: 11-2008
DOI: 10.1016/J.JPBA.2008.06.022
Abstract: A review with 98 references. The determination of the opium poppy (Papaver somniferum) alkaloids and their semi-synthetic derivatives has important applications in industrial process monitoring, clinical analysis and forensic science. Liquid-phase chemiluminescence reagents such as tris(2,2'-bipyridyl)ruthenium(II) and acidic potassium permanganate exhibit remarkable sensitivity and complementary selectivity for many P. somniferum alkaloids, which has been exploited in the development of a range of analytical procedures using flow analysis, high-performance liquid chromatography, capillary electrophoresis and microfluidic instrumentation.
Anion recognition and anion-mediated self-assembly with thiourea-functionalised fused [3]polynorbornyl frameworks
Publisher: Royal Society of Chemistry (RSC)
Date: 2007
DOI: 10.1039/B703208K
Abstract: Three conformationally preorganised host molecules based on the [3]polynorbornyl framework and incorporating di-urea receptors were synthesised and their interaction with a series of anions investigated by (1)H NMR spectroscopy. A high affinity of each host molecule for dihydrogenphosphate (H(2)PO(4)(-)) and dihydrogenpyrophosphate (H(2)P(2)O(7)(2-)) was identified. In addition to binding to the urea receptors of the host molecules, evidence for an interaction involving the non-polar C-H groups within the binding cavity of the framework and guest anions was also discovered. Furthermore, an unusual 2 : 1 host-to-anion stoichiometry was indicated when binding H(2)P(2)O(7)(2-), and a model for the anion-mediated self-assembly of this complex species is proposed.
Synthesis of 3,4-dihydroxy-1,8-naphthalimides with inbuilt catechol and crown ether functionalities
Publisher: Royal Society of Chemistry (RSC)
Date: 2023
DOI: 10.1039/D3OB00737E
Abstract: Herein the synthesis of 1,8-naphthalimides functionalised as the 3,4-dihydroxy-1,8-naphthalimide (catechol, Nap-Cat) and the corresponding 15-crown-5 (Nap-Crown) is reported.
Steric and electronic factors influencing recognition by a simple, charge neutral norbornene based anion receptor
Publisher: Royal Society of Chemistry (RSC)
Date: 2007
DOI: 10.1039/B703626B
Abstract: Based on (1)H NMR studies, subtle electronic factors rather than pre-organisation dictate the binding stoichiometry of the new, norbornene based, anion hosts 1 and 2 with acetate, however, the binding of dihydrogenphosphate appears to be based solely on steric constraints.
Rapid Solvent‐Free Synthesis of Pyridyl‐Functionalised [5]Polynorbornane‐Based Ligands for Metal–Organic Rings and Cages
Publisher: Wiley
Date: 24-07-2013
Colorimetric and fluorescent anion sensors: An overview of recent developments in the use of 1,8-naphthalimide-based chemosensors
Publisher: Royal Society of Chemistry (RSC)
Date: 2010
DOI: 10.1039/B910560N
Abstract: This critical review focuses on the development of anion sensors, being either fluorescent and/or colorimetric, based on the use of the 1,8-naphthalimide structure a highly versatile building unit that absorbs and emits at long wavelengths. The review commences with a short description of the most commonly used design principles employed in chemosensors, followed by a discussion on the photophysical properties of the 4-amino-1,8-naphthalimide structure which has been most commonly employed in both cation and anion sensing to date. This is followed by a review of the current state of the art in naphthalimide-based anion sensing, where systems using ureas, thioureas and amides as hydrogen-bonding receptors, as well as charged receptors have been used for anion sensing in both organic and aqueous solutions, or within various polymeric networks, such as hydrogels. The review concludes with some current and future perspectives including the use of the naphthalimides for sensing small biomolecules, such as amino acids, as well as probes for incorporation and binding to proteins and for the recognition/sensing of polyanions such as DNA, and their potential use as novel therapeutic and diagnostic agents (95 references).
Conformationally preorganised hosts for anions using norbornane and fused [n]polynorbornane frameworks
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C3CC40702K
Abstract: Norbornane and fused [n]polynorbornane frameworks are readily synthesised, can be tailored to a variety of predictable geometries and can be functionalised regiospecifically. As such, these highly preorganised scaffolds offer the supramolecular chemist an excellent starting point when designing hosts for specific guests. This feature article will highlight the evolution of our research from relatively simple norbornane based anion receptors to more sophisticated tetrathioureido functionalised fused [n]polynorbornane hosts.
Synthesis and polymerization studies of 3-(+) and (-)-menthyl carboxylate pyrroles
Publisher: Elsevier BV
Date: 11-2007
Domino heck-aza-michael reactions: efficient access to 1-substituted tetrahydro-β-carbolines
Publisher: American Chemical Society (ACS)
Date: 04-02-2010
DOI: 10.1021/JO902652H
Abstract: A simple and efficient palladium-catalyzed domino reaction for the synthesis of a series of C1-substituted tetrahydro-beta-carbolines is described. This domino process involves a Heck reaction at the indole 2-position of a halogenated tryptamine precursor, followed by intramolecular aza-Michael addition.
4-Amino-1,8-naphthalimide-based anion receptors: Employing the naphthalimide N-H moiety in the cooperative binding of dihydrogenphosphate
Publisher: Elsevier BV
Date: 09-2005
Synthesis of 2-[2-(tert-butoxycarbonyl)-3-(acyl)guanidino]ethylamine salts for convergent introduction of acyl guanidines
Publisher: Royal Society of Chemistry (RSC)
Date: 2022
DOI: 10.1039/D2NJ01510B
Abstract: A series of acylguanidines with pre-installed ethylamino linkers are described that can be incorporated into larger structures through amide coupling.
Asymmetric induction in domino Heck-aza-Michael reactions
Publisher: Elsevier BV
Date: 03-2012
Photoredox catalysis of intramolecular cyclizations with a reusable silica-bound ruthenium complex
Publisher: Wiley
Date: 07-05-2015
Blue Electrogenerated Chemiluminescence from Water-Soluble Iridium Complexes Containing Sulfonated Phenylpyridine or Tetraethylene Glycol Derivatized Triazolylpyridine Ligands
Publisher: Wiley
Date: 03-09-2015
Abstract: Incorporating phenylpyridine- and triazolylpyridine-based ligands decorated with methylsulfonate or tetraethylene glycol (TEG) groups, a series of iridium(III) complexes has been created for green and blue electrogenerated chemiluminescence under analytically useful aqueous conditions, with tri-n-propylamine as a coreactant. The relative electrochemiluminescence (ECL) intensities of the complexes were dependent on the sensitivity of the photodetector over the wavelength range and the pulse time of the applied electrochemical potential. In terms of the integrated area of corrected ECL spectra, with a pulse time of 0.5 s, the intensities of the Ir(III) complexes were between 18 and 102 % that of [Ru(bpy)3 ](2+) (bpy=2,2'-bipyridine). However, when the intensities were measured with a typical bialkali photomultiplier tube, the signal of the most effective blue emitter, [Ir(df-ppy)2 (pt-TEG)](+) (df-ppy=2-(2,4-difluorophenyl)pyridine anion, pt-TEG=1-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)-4-(2-pyridyl)-1,2,3-triazole), was over 1200 % that of the orange-red emitter [Ru(bpy)3 ](2+) . A combined experimental and theoretical investigation of the electrochemical and spectroscopic properties of the Ir(III) complexes indicated that the greater intensity from [Ir(df-ppy)2 (pt-TEG)](+) relative to those of the other Ir(III) complexes resulted from a combination of many factors, rather than being significantly favored in one area.
The presence of GABA in gastropod mucus and its role in inducing larval settlement
Publisher: Elsevier BV
Date: 2008
Fluorescent Photoinduced Electron Transfer (PET) sensors for anions; From design to potential application
Publisher: Springer Science and Business Media LLC
Date: 05-2005
DOI: 10.1007/S10895-005-2627-Y
Abstract: This mini review highlights the synthesis and photophysical evaluation of anion sensors, for nonaqueous solutions, that have been developed in our laboratories over the last few years. We have focused our research mainly on developing fluorescent photoinduced electron transfer (PET) sensors based on the fluorophore-spacer-anion receptor principle using several anthracene (emitting in the blue) and 1,8-naphthalimide (emitting in the green) fluorophores, with the aim of targeting biologically and industrially relevant anions such as acetates, phosphate and amino acids, as well as halides such as fluoride. The receptors and the fluorophore are separated by a short methyl or ethyl spacer, where the charge neutral anion receptors are either aliphatic or aromatic urea (or thiourea) moieties. For these, the anion recognition is through hydrogen bonding, yielding anion:receptor complexes. Such bonding gives rise to enhanced reduction potential in the receptor moieties which causes enhancement in the rate of PET quenching of the fluorophore excited state from the anion:receptor moiety. This design can be further elaborated on by incorporating either two fluorophores, or urea/thiourea receptors into the sensor structures, using anthracene as a fluorophore. For the latter design, the sensors were designed to achieve sensing of bis-anions, such as di-carboxylates or pyrophosphate, where the anion bridged the anthracene moiety. In the case of the naphthalimide based mono-receptor based PET sensors, it was discovered that in DMSO the sensors were also susceptible to deprotonation by anions such as F(-) at high concentrations. This led to substantial changes in the absorption spectra of these sensors, where the solution changed colour from yellow/green to deep blue, which was clearly visible to the naked eye. Hence, some of the ex les presented can act as dual fluorescent-colorimetric sensors for anions. Further investigations into this phenomenon led to the development of simple colorimetric sensors for fluorides, which upon exposure to air, were shown to fix carbon dioxide as bicarbonate.
Fluorescence and conductivity studies on wool
Publisher: Elsevier BV
Date: 2009
A fluorescent histone deacetylase (HDAC) inhibitor for cellular imaging
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C5CC02059J
Abstract: Fluorescent 4MS , has comparable HDAC and anticancer activity to scriptaid and allows visualisation of rapid cellular uptake and cytoplasmic localisation.
To Cooperate or Not: The Role of Central Functionality in Bisthiourea [6]polynorbornane Hosts
Publisher: Wiley
Date: 07-10-2019
A rhodamine–naphthalimide–benzamide trichromophoric system with solid-state and multiple solvent dependent aggregate emissive properties
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D1QM00397F
Abstract: The readily synthesised rhodamine–naphthalimide–benzamide trichromophoric system forms unique AIE emissive species in DMSO solutions with traces of water ( %) and high water content ( %) and responds to pH changes in both solution and solid state.
Norbornane-based antibacterial agents: Benzyl and benzoyl substituted guanidines
Publisher: Elsevier BV
Date: 12-2022
A rhodamine-nitronaphthalimide Hg(II) complex for the simultaneous detection of oxidised and reduced glutathione
Publisher: Elsevier BV
Date: 12-2019
An optimised synthesis of 2-[2,3-Bis(tert -butoxycarbonyl)guanidino] ethylamine
Publisher: Georg Thieme Verlag KG
Date: 07-2012
Developing an anion host for lipid A binding and antibacterial activity
Publisher: Royal Society of Chemistry (RSC)
Date: 2010
DOI: 10.1039/B925135A
Abstract: New structural hiphiles 2a and 2b bind the diphosphate lipid A anion and show potential as lead compounds for the development of novel antibacterial agents.
A screening test for heroin based on sequential injection analysis with dual-reagent chemiluminescence detection
Publisher: Elsevier BV
Date: 30-07-2008
DOI: 10.1016/J.TALANTA.2008.04.012
Abstract: A sequential injection analysis procedure with dual-reagent chemiluminescence detection was applied to the screening of street drug seizure s les for the presence of heroin. The chemiluminescence reagents (acidic potassium permanganate and tris(2,2'-bipyridine)ruthenium(III)) were aspirated from either side of a s le aliquot that was sufficiently large to prevent interdispersion of the reagent zones, and therefore two different chemical reactions could be performed simultaneously at either end of the s le zone. The presence of heroin in seizure s les was indicated by a strong response with the tris(2,2'-bipyridine)ruthenium(III) reagent and confirmed by a significant increase in the response with the permanganate reagent when the s le was treated with sodium hydroxide to hydrolyse the heroin to morphine. Nicomorphine (a morphine-derived pharmaceutical) was synthesised and tested under the same conditions. The responses with the permanganate reagent were similar to those for heroin, which supports the proposed chemical basis for the test. However, the responses with tris(2,2'-bipyridine)ruthenium(III) were far lower for nicomorphine than heroin (approximately 5-fold for the s les that had not been hydrolysed).
Synthesis of N-substituted 4-hydroxynaphthalimides using palladium-catalysed hydroxylation
Publisher: Elsevier BV
Date: 03-2016
Corrosion-resistant coatings for magnesium (Mg) alloys
Publisher: Elsevier
Date: 2013
Desymmetrization of an Octahedral Coordination Complex Inside a Self‐Assembled Exoskeleton
Publisher: Wiley
Date: 6
Abstract: The synthesis of a centrally functionalized, ribbon-shaped [6]polynorbornane ligand L that self-assembles with Pd(II) cations into a {Pd2 L4 } coordination cage is reported. The shape-persistent {Pd2 L4 } cage contains two axial cationic centers and an array of four equatorial H-bond donors pointing directly towards the center of the cavity. This precisely defined supramolecular environment is complementary to the geometry of classic octahedral complexes [M(XY)6 ] with six diatomic ligands. Very strong binding of [Pt(CN)6 ](2-) to the cage was observed, with the structure of the host-guest complex {[Pt(CN)6 ]@Pd2 L4 } supported by NMR spectroscopy, MS, and X-ray data. The self-assembled shell imprints its geometry on the encapsulated guest, and desymmetrization of the octahedral platinum species by the influence of the D4h -symmetric second coordination sphere was evidenced by IR spectroscopy. [Fe(CN)6 ](3-) and square-planar [Pt(CN)4 ](2-) were strongly bound. Smaller octahedral anions such as [SiF6 ](2-) , neutral carbonyl complexes ([M(CO)6 ] M=Cr, Mo, W) and the linear [Ag(CN)2 ](-) anion were only weakly bound, showing that both size and charge match are key factors for high-affinity binding.
Organogelators based on the norbornane scaffold
Publisher: Informa UK Limited
Date: 13-12-2015
Highly fluorescent and HDAC6 selective scriptaid analogues
Publisher: Elsevier BV
Date: 2019
DOI: 10.1016/J.EJMECH.2018.11.020
Abstract: Fluorescent scriptaid analogues with excellent HDAC6 selectivity (HDAC1/6 > 500) and potency (HDAC6 IC
Factors influencing anion binding stoichiometry: The subtle influence of electronic effects
Publisher: Wiley
Date: 03-2008
Examples of Regioselective Anion Recognition among a Family of Two-, Three-, and Four-“Armed” Bis-, Tris-, and Tetrakis(thioureido) [n]Polynorbornane hosts
Publisher: American Chemical Society (ACS)
Date: 26-09-2012
DOI: 10.1021/JO301450B
Abstract: A family of conformationally preorganized, [n]polynorbornane-based anion hosts 1a,b-6a,b have been synthesized. The series includes receptors with 4, 8, and 12 H-bond donors. Using (1)H NMR titration techniques, evaluation of the new hosts against a series of alkyl and aryl dicarboxylates as well as a range of phosphoanionic species has revealed that the tris(thioureido) hosts (in particular 3a) are capable of regioselectively binding dicarboxylates and pyrophosphate (H(2)PPi(2-)).
Facile synthesis of guanidine functionalised building blocks
Publisher: Wiley
Date: 19-01-2015
Microwave-accelerated 1,3-dipolar cycloaddition for the formation of fused [n]polynorbornanes
Publisher: Elsevier BV
Date: 05-2009
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