Australian Journal of Chemistry
Volume 70 Number 11 2017
RACI and AAS Awards (2016/2017)
This special issue of the Journal presents papers authored by RACI and AAS award winners from 2016 and 2017.
CH17391Synthesis of Star Polymers by RAFT Polymerization as Versatile Nanoparticles for Biomedical Applications
Synthesis of star polymers using reversible addition–fragmentation chain transfer (RAFT) polymerization through core-first and arm-first preparation are outlined. Biomedical applications of the resulting star polymers in controlled delivery of chemotherapeutic agents, protein inhibitors, signalling molecules, siRNA, and in constructing macromolecular magnetic resonance imaging (MRI) contrast agents and fluorescent imaging agents, and theranostic vectors are discussed.
A new porous 3-dimensional coordination framework containing the novel photoactive ligand 5-((4-tert-butyl)phenylazo)isophthalic acid displays light-dependent spectroscopic properties.
The reactions of classic iridium and rhodium complexes with iodine(iii) oxidants are described. All reactions resulted in two-electron oxidation. Ligand exchange and anion scrambling were observed in monodentate ligand-containing complexes. In the case of reacting Iiii reagents with chelating ligand-containing complexes, no scrambling was observed, leading to the isolation of well-defined complexes.
A range of 3-hydroxymethylindoles undergo acid-catalysed reactions involving ipso-electrophilic substitution with the extrusion of methanal and the formation of diindolylmethane moieties. Both inter- and intramolecular processes lead to macrocyclic compounds.
The synthesis of 21-membered imine- and amine-linked tris-indole macrocycles starting from 7-nitroethylindoles is described.
CH17380Application of Hole-Transporting Materials as the Interlayer in Graphene Oxide/Single-Wall Carbon Nanotube Silicon Heterojunction Solar Cells
New hole-transport materials have been applied in silicon–carbon nanotube solar cells to yield better performance.
CH17363Laser-Based Formation of Copper Nanoparticles in Aqueous Solution: Optical Properties, Particle Size Distributions, and Formation Kinetics
The formation of copper nanoparticles (CuNPs) in the presence of N-donor ligands results in changes in the nanoparticle optical properties and particle size distributions, depending on the nature of the donor ligands. CuNP formation kinetics are independent of the nature of the donor ligand.
CH17440Internal Energy Deposition in Dielectric Barrier Discharge Ionization is Significantly Lower than in Direct Analysis in Real-Time Mass Spectrometry
Portable dielectric barrier discharge ionization is a plasma-based ion source for mass spectrometry that is significantly ‘softer’ than the two most widely used plasma-based ionization sources. This is important for the detection of intact molecules with thermolabile bonds, such as many explosives, and some chemical weapons and organic pollutants.
CH17335Redox-State Dependent Spectroscopic Properties of Porous Organic Polymers Containing Furan, Thiophene, and Selenophene
Redox-active porous organic polymers with heterocyclic linkers (furan, thiophene, and selenophene) have been synthesised and their electronic and spectroscopic properties investigated as a function of redox state. Through the use of electron paramagnetic resonance spectroelectrochemistry, it was found that the distinct redox states in these polymers could be reversibly accessed.
CH17228The Use of Imaging Mass Spectrometry to Study Peptide Toxin Distribution in Australian Sea Anemones
Peptide toxins from sea anemones may provide valuable drug leads. However, little is known about peptide toxin distribution in discrete morphological regions in sea anemones, which perform distinct biological functions. We utilise imaging mass spectrometry to examine peptide distribution in the Australian sea anemone, Oulactis muscosa, and infer biological function.
The peer-reviewed and edited version of record published online before inclusion in an issue
CH17472Quantum-Chemical Ab Initio Calculations on Inda- and Thallabenzene (C5H5In and C5H5Tl) and their Structural Isomers η5-C5H5In and η5-C5H5Tl
Quantum-chemical calculations were performed on the so far elusive compounds inda- and thallabenzene. The ground states of both compounds were found to be triplets with the lowest closed-shell singlets up to 3 kcal mol−1 higher in energy. The η5 isomers were found to be energetically up to 102 kcal mol−1 below the six-membered rings.
CH17498Two Coordination Polymers Constructed from Pentanuclear Zinc Clusters with Triazolate and Benzenecarboxylate Ligands: Selective Gas Adsorption
Introduction of the 1,3,5-benzenetricarboxylate into the zinc-triazolate system gave the 3D porous structure of 1 based on pentanuclear [Zn5(μ3-OH)2] clusters and exhibited selective gas adsorption. While a variation of BTC3−, the 5-sulfoisophthalate was introduced into the zinc-triazolate system yielding a non-porous structure of 2 constructed from pentanuclear [Zn5(trz)8] clusters, demonstrating that the secondary ligands play an important role in the formation of the final structures.
CH17341Regioselective Synthesis of 2,5-Disubstituted Pyrroles via Stepwise Iododesilylation and Coupling Reactions
The regioselective preparation of 2,5-disubstituted pyrroles, useful structural scaffolds, is important. To this end, a protocol based on a stepwise iododesilylation and a subsequent coupling reaction, involving a 6-step pathway starting from the simplest pyrrole, has been realised. This methodology can be widely used in the synthesis of drugs, molecular wires, and high-molecular-weight polymers.
CH17484Structural Variations in the Complete Series of Lanthanoid Complexes of a Calixarene Trisamide
Co-ligand binding in a sequence of calixarene complexes changes as a function of lanthanoid cation size.
A Co-W nanofibre sensor was found to exhibit excellent gas-sensing properties at room temperature, such as a response of 1.17 and 3 s to 1000 ppm NH3, and the response time always remained within 5 s for a NH3 concentration range of 1000–10 ppm, due to the single crystal CoWO4–CoWO4 homojunctions and unique massage ball-like WO3–CoWO4 heterojunctions.
CH17359First Year Introductory Chemistry at the University of Western Australia: Reflections and Perceptions
This study investigated the motivations and attitudes of two student cohorts enrolled in an introductory chemistry unit, which Emeritus Professor Graham Chandler helped to create. An interview with Graham describes the origins of this unit. Therefore, this study has particular interest in this special issue celebrating Graham’s career in chemistry.
CH17334A Novel Strategy to Introduce 18F, a Positron Emitting Radionuclide, into a Gallium Nitrate Complex: Synthesis, NMR, X-Ray Crystal Structure, and Preliminary Studies on Radiolabelling with 18F
Substituted diphenyl dithiosemicarbazone gallium nitrate and fluoride complexes have been synthesised and the structures confirmed by NMR and X-ray crystallography. Radiolabelling of the nitrate complexes has been performed with fluorine-18, resulting in the formation of Ga-18F complexes.
CH17214An Injectable Oxidized Carboxymethyl Cellulose/Polyacryloyl Hydrazide Hydrogel via Schiff Base Reaction
A series of injectable oxi-CMC/PAH hydrogels was prepared via a Schiff base reaction under physiological conditions. The oxi-CMC6/PAH3 hydrogel exhibited good comprehensive properties and in vitro sustained release of BSA, showing that it could be potentially applied in the fields of drug delivery vehicles, tissue engineering, and cell encapsulation materials.
A surface modification method is presented where sodium chloride crystal was deposited onto a stainless steel surface. The surface was subjected to various stimuli to induce surface defects either on the surface or crystal and the ion yield of substance P was investigated as a function of stimuli. The interaction of the laser resulted in an increase in the ion yield of substance P (3–17 fold increase relative to no stimuli).
CH17348Tetraiodoallene, I2C=C=CI2 – the missing link between I2C=CI2 and I2C=C=C=CI2 – and the oxidation product, 2,2-diiodoacrylicacid, I2C=CH(CO2H)
Crystal structures of tetraiodoallene, C3I4, and 2,2-diiodoacrylic acid, I2C=CH(CO2H), are reported.
CH17255N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XIV. Synthesis and Reactivity of the New Benzo[4,5]imidazo[1,2-b][1,2,6]thiadiazine Ring System
N,N-Dialkyl-N′-chlorosulfonyl chloroformamidines 1 reacted regioselectively with benzimidazoles bearing an activated methylene group at C2 to afford derivatives of the new benzo[4,5]imidazo[1,2-b][1,2,6]thiadiazine ring system. Substitution reactions of the new system occurred selectively at N5 (not at N2).
CH174761,3-Dipolar Cycloaddition of a Nitronyl Nitroxide-Substituted Alkyne to Heteroaromatic N-Imines
We report on the 1,3-dipolar cycloaddition of the triple bond in an ethynyl-substituted nitronyl nitroxide to heteroaromatic N-imines. The reaction opens a new pathway to polyfunctional nitronyl nitroxides with pyrazolo[1,5-a]pyridine or related substituents that are in demand in coordination chemistry and molecular magnetism fields.
CH17202Investigation of Hybrid Materials Based on Polyurethane Modified with Aliphatic Side Chains Combined with Nano-TiO2
Polyurethanes (PUs) were synthesised using methylene diphenyl diisocyanate (MDI), polytetrahydrofuran ether diol (PTMG), and chain extenders containing different amounts of aliphatic side chains. Hybrid materials were then prepared by reacting the PUs with nano-TiO2. The effects of different molecular structures of the chain extenders on the surface properties of PU coatings and the hybrid materials were investigated.
A simple, multigram-scale preparation of 1,4-bis(trimethylsilyl)buta-1,3-diyne that minimises risks associated with the preparation of this useful compound is reported.
The catalytic activity of nanofibre sepiolite as a green and non-toxic catalyst was investigated in the synthesis of chromene derivatives.
CH17154Microwave-Assisted Conversion of Fructose to 5-Hydroxymethylfurfural Using Sulfonated Porous Carbon Derived from Biomass
A series of carbon-based solid acid catalysts derived from biomass was prepared and used for the conversion of fructose to 5-HMF, which is a very important platform chemical due to its unique chemical structure. The results suggest that sulfonated carbon materials exhibit remarkable catalytic capability for fructose dehydration to 5-HMF.
CH17277A Novel Cancer Nanotheranostics System Based on Quantum Dots Encapsulated by a Polymer-Prodrug with Controlled Release Behaviour
A prodrug mPEG-b-PCL-(g-PTX)-b-PLA-(g-LA) has been synthesized, which may exchange ligands with QDs to form a nanotheranostic system (prodrug-co-QDs). This novel system exhibited good controlled drug release behaviour due to the ester linkage between the drug and polymer. By using typical cancer cell lines, we showed that this nanotheranostic system is promising in cancer diagnosis and treatment in vitro.
CH17219New Insights into the Origin of the cis-Configuration Preferences in 1,2-Dihaloethenes: The Importance of the Bonding Orbital Deviations
The co-operative stabilizations associated with the bending of the σC–C toward C–F bonds and total hyperconjugative generalized anomeric effect in the cis-configuration of 1,2-difluoroethene overcome the destabilizations associated with the exchange component and dipole–dipole interactions, leading to the preference of the cis-configuration in the compound.
CH17248New Organic Acidic Cyclohexaphosphate: Synthesis, Crystal Structure, Physicochemical Study, and In Vitro Biochemical Investigation
The present paper reports a new hybrid cyclohexaphosphate which was characterized by different techniques (NMR, IR, UV-vis) and evaluated (electrical and biological). This reported compound exhibits an acidic character which is rarely observed with this type of condensed phosphate. In addition, this material is distinguished from others by its higher thermal stability and more pronounced antioxidant activity.
CH17310Rational Design of Azo-Azomethine Receptors for Sensing of Inorganic Fluoride: Construction of Molecular Logic Gates and DFT Study
New azomethine receptors were designed and synthesised for rapid and naked eye detection of inorganic fluoride anions in semi-aqueous media. The sensing ability of the receptors towards F− has been investigated spectroscopically. By using F− and H+ as chemical inputs and the absorbance as output, an INHIBIT logic gate was constructed, which exhibits ‘Write–Read–Erase–Read’ ability without obvious degradation in its optical output.
CH17146A Simple and Efficient Diversity-Oriented Synthesis of New Substituted 3-(Arylamino)-6,7-dihydro-1H-indazol-4(5H)-ones by a KOH-Assisted One-Pot Reaction
A novel, simple and straightforward combinatorial method for the synthesis of new substituted 3-(arylamino)-6,7-dihydro-1H-indazol-4(5H)-one derivatives has been developed. The synthesis was achieved via a one-pot three-component reaction of aromatic isothiocyanates, substituted 1,3-cyclohexanediones, and hydrazine hydrate in dimethyl sulfoxide.
CH17325Star-Shaped Copolymers Based on Poly(N-vinylcaprolactam) and their Use as Nanocarriers of Methotrexate
Star-shaped block copolymers based on poly(N-vinylcaprolactam) and functionalized with polyethylene glycol have been synthesized. The star-shaped block copolymers self-assemble spontaneously into aggregates in water and were used to encapsulate methotrexate.
CH17272A Facile and Convenient Approach for the Synthesis of Novel Sesamol–Oxazine and Quinoline–Oxazine Hybrids
Novel 1,3-oxazine hybrids of sesamol and quinoline have been synthesized via one-pot reaction of sesamol/6-hydroxyquinoline, aromatic amines, and formaldehyde. The structures of all the novel compounds were confirmed by spectral data. The structure of the synthesized hybrids was also confirmed by X-ray crystallographic studies.
CH17220Recognition of a Flavin Analogue by Novel Bile Acid-Based Receptors: Effects of Hydrogen Bonding and Aromatic π-Stacking Interactions
Synthesis and binding behaviour of bile acid-based flavin receptors containing 2,6-diaminopyridine and aromatic moieties are reported. These receptors display significant influence of steric and aromatic π-stacking interactions, along with hydrogen bonding, on their binding with N-(10)-hexylflavin derivative.
CH17168Alkali Metal Ion-Exchanged Zeolite X from Bamboo Leaf Biomass as Base Catalysts in Cyanoethylation of Methanol Enhanced by Non-Microwave Instant Heating
Zeolite X base catalysts containing alkali metal ions are prepared from amorphous bamboo leaf ash. The catalysts are found to be highly active in cyanoethylation of methanol under an instant heating environment that mimics microwave fast heating.
CH17206Experimental and Theoretical Investigation of the Reaction of Secondary Amines with Maleic Anhydride
Secondary amines react with maleic anhydride under kinetic control across the C=O functionality exclusively. The product changes into N-substituted maleimic acid under thermodynamic control. The Fukui functions determined at the B3LYP/6-31G* level reveal that the carbon atom of the carbonyl group is the hardest site, thus making it the preferred site for the nucleophilic attack.
CH17270Synthesis and Crystal Structure of Unexpected (1S,4R,5R,6S)-4-Cyano-2,2,6-trimethyl-3-azabicyclo[3.3.1]nonan-6-yl Acetate
A novel alkaloid-like compound containing the azabicyclo[3.3.1]nonane core is reported to be the first instance of using the bridged Ritter reaction with hydrogen cyanide. The structure of this unique and unexpected compound was determined with the aid of X-ray crystallography.
These articles have been peer reviewed and accepted for publication. They are still in production and have not been edited, so may differ from the final published form.
Host (−)-(2R,3R)-2,3-Dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol and Guests Aniline, N-Methylaniline and N,N-Dimethylaniline: A Selectivity Study
Phosphate and phosphonate based ionic liquids as new additives in Foeniculum vulgare essential oil extraction
Highly ordered supramolecular nanoassemblies of paramagnetic amphiphilic chelates as potential MRI contrast agents
A computational investigation of the uncatalysed and water-catalysed acyl rearrangements in ingenol esters
Quantum-Chemical Ab Initio Calculations on Inda- and Thallabenzene (C5H5In and C5H5Tl) and their Structural Isomers η5-C5H5In and η5-C5H5Tl
Perspective view of Metal Organic Frameworks and other existing materials as a drug delivery carrier
Synthesis and characterization of Co1-xCuxFe2-xAlxO4 ferrite nano-scales as a potential candidate for high density data storage applications
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