Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science

Australian Journal of Chemistry

Australian Journal of Chemistry

Australian Journal of Chemistry - an International Journal for Chemical Science publishes research papers from all fields of chemical science, with a focus on multidisciplinary chemistry and emerging areas of research. Read more about the journalMore

Editors-in-Chief: George Koutsantonis and John Wade

Current Issue

Australian Journal of Chemistry

Volume 70 Number 9 2017

RESEARCH FRONT: Dedication to Professor Alan Bond

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Grafting from aryldiazonium salts is a popular method for preparing strongly adherent organic coatings on many surfaces. Usually, the coatings are loosely packed disordered multilayers; however, over the past decade, strategies have emerged for generating monolayers. This review describes these approaches, illustrates some of their applications, and highlights the advantages and disadvantages of each.

CH17187Transformation of Cadmium Tetracyanoquinodimethane (TCNQ) into a Cadmium Terephthalate Metal–Organic Framework

Manzar Sohail, Farooq Ahmad Kiani, Vedapriya Pandarinathan, Safyan Akram Khan, Damien J. Carter, Roland De Marco and Alan M. Bond
pp. 973-978
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Aerial oxidation of Cd(TCNQ)2 during slow recrystallization in tetrahydrofuran produced a dicarboxylate ligand–Cd complex, with the N 1s XPS spectrum showing that this chemical transformation is complete.

CH17191A Potentiometric Sensor for pH Monitoring with an Integrated Electrochromic Readout on Paper

Edith Chow, Devi D. Liana, Burkhard Raguse and J. Justin Gooding
pp. 979-984
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An integrated device is developed that incorporates a sensor, readout system, and battery on paper. The electrochromic readout system allows the pH range of a sample solution to be determined visually rather than using an LCD display or voltmeter. The integrated potentiometric sensor and readout system provides a cost-effective and lightweight solution for pH monitoring.

CH17258Electropolymerisation of N-Ethylanilinium Trifluoroacetate Ionic Liquid into Poly(N-Ethylaniline) and Control of its Morphology

Muhammad E. Abdelhamid, Graeme A. Snook, Tamar L. Greaves and Anthony P. O'Mullane
pp. 985-989
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The electropolymerisation of N-ethylanilinium trifluoroacetate, a protic ionic liquid (PIL), was carried out, where the PIL served as the monomer precursor, solvent, and supporting electrolyte for the polymerisation process resulting in different morphologies, a greener approach to production, and a highly processable polymer.

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Electrochemical determination of mass-transport parameters is often subject to small errors, which influence the outcomes of voltammetric experiment–theory comparisons. In particular, a perilous situation emerges when a quasi-reversible model with slightly overestimated mass-transport parameters is used to quantify the electrode kinetics for a system that approaches a reversible limit.

CH17245Structural, Spectroscopic, and Electrochemical Characterization of Semi-Conducting, Solvated [Pt(NH3)4](TCNQ)2·(DMF)2 and Non-Solvated [Pt(NH3)4](TCNQ)2

Jinzhen Lu, Ayman Nafady, Brendan F. Abrahams, Muhammad Abdulhamid, Bjorn Winther-Jensen, Alan M. Bond and Lisandra L. Martin
pp. 997-1005
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Two related [Pt(NH3)4]2+ complexes, [Pt(NH3)4](TCNQ)2·(DMF)2 (1) and [Pt(NH3)4](TCNQ)2 (2) are characterized using X-ray, electrochemistry, vibrational, and electronic spectroscopy. Unexpectedly, 2 is not a catalyst for the redox reaction of ferricyanide and thiosulfate, and the rationale for this is presented.

CH17256Electrochemical Oxidation of W(CO)4(LL): Generation, Characterization, and Reactivity of [W(CO)4(LL)]+ (LL=α-diimine ligands)

John P. Bullock, Chong-Yong Lee, Brian Hagan, Humair Madhani and John Ulrich
pp. 1006-1015
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Oxidations of W(CO)4(LL) compounds were investigated electrochemically. The electrogenerated radical cations are unstable toward disproportionation, carbon monoxide substitution, and nucleophilic attack. The kinetics of these reactions were examined using a number of techniques including a.c. voltammetry and chronocoulometry. Infrared spectroelectrochemistry was used to characterize two [W(CO)4(LL)]+ species.

CH17281Zinc Electrodeposition in the Presence of an Aqueous Electrolyte Containing 1-Ethylpyridinium Bromide: Unexpected Oddities

Max E. Easton, Lisa C. Player, Anthony F. Masters and Thomas Maschmeyer
pp. 1025-1031
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The generation of a radical species from the reduction of 1-ethylpyridiniuim bromide has been shown to passivate Zn/ZnII redox after one cycle. Both deposition morphology and nucleation process are also altered in the presence of the radical species.

CH17141Polymorphs of Neutral Red, a Redox-Mediating Phenazine in Biological Systems

Mackenzie Labine-Romain, Sabrina Beckmann, Mohan Bhadbhade, Saroj Bhattacharyya, Michael Manefield, Christopher E. Marjo and Anne M. Rich
pp. 1032-1038
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Crystalline neutral red accelerates microbial methane generation from coal. Industrial scale-up requires knowledge of crystalline polymorphs that may behave differently with methanogens. Temperatures in the dark, subterranean environments where methanogenesis occurs range from 50–70°C, conditions where neutral red crystallises or transforms to a new polymorph.

CH17089MoO2 Formed on Mesoporous Graphene Oxide: Efficient and Stable Catalyst for Epoxidation of Olefins

Gang Bian, Pingping Jiang, Kelei Jiang, Yirui Shen, Linggang Kong, Ling Hu, Yuming Dong and Weijie Zhang
pp. 1039-1047
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A novel MoO2 composite supported on mesoporous graphene oxide (m-MoO2/GO) is successfully synthesised. The introduction of a mesoporous structure into GO sheets not only promotes the catalytic activity, but also makes m-MoO2/GO more effective in catalysing olefins with a long carbon chain and large ring size.

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A series of all-trans acceptor–π-donor (acceptor) compounds were conveniently synthesised via the three-step synthetic method Arbuzov reaction, solvent-free Horner–Wadsworth–Emmons reaction, and Mizoroki–Heck reaction. They all exhibit obvious solvatochromic effects, strong two-photon excited fluorescence, and large two-photon absorption cross-sections.

CH17062Effects of Gold Nanoparticles and Gold Anti-Arthritic Compounds on Inflammation Marker Expression in Macrophages

Lloyd R. A. James, Ron Sluyter, Carolyn T. Dillon and Stephen F. Ralph
pp. 1057-1068
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The ability of gold anti-arthritic agents and gold nanoparticles to alter production in RAW264.7 macrophages of a number of cellular mediators of inflammation, including reactive oxygen and nitrogen species, interleukin-10 and tumour necrosis factor, have been compared.

Online Early

The peer-reviewed and edited version of record published online before inclusion in an issue

Published online 21 September 2017

CH174761,3-Dipolar Cycloaddition of a Nitronyl Nitroxide-Substituted Alkyne to Heteroaromatic N-Imines

Vasiliy Romanov, Aleksey Vorob'ev, Irina Bagryanskaya, Dmitriy Parkhomenko and Evgeny Tretyakov
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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.

Published online 20 September 2017

CH17202Investigation of Hybrid Materials Based on Polyurethane Modified with Aliphatic Side Chains Combined with Nano-TiO2

Jie Zhang, Nanjie Zhang, Quan Liu, Haojun Ren, Pengfei Li and Kang Yang
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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.

Published online 15 September 2017

CH17363Laser-Based Formation of Copper Nanoparticles in Aqueous Solution: Optical Properties, Particle Size Distributions, and Formation Kinetics

Ashley J. Mulder, Rhys D. Tilbury, Phillip J. Wright, Thomas Becker, Massimiliano Massi and Mark A. Buntine
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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.

Published online 13 September 2017

CH17391Synthesis of Star Polymers by RAFT Polymerization as Versatile Nanoparticles for Biomedical Applications

Jinming Hu, Ruirui Qiao, Michael R. Whittaker, John F. Quinn and Thomas P. Davis
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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.

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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.

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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.

Published online 31 August 2017

CH17380Application of Hole-Transporting Materials as the Interlayer in Graphene Oxide/Single-Wall Carbon Nanotube Silicon Heterojunction Solar Cells

LePing Yu, Tom Grace, Hong Duc Pham, Munkhbayar Batmunkh, Mahnaz Dadkhah, Cameron Shearer, Prashant Sonar and Joe Shapter
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New hole-transport materials have been applied in silicon–carbon nanotube solar cells to yield better performance.

Published online 29 August 2017

CH17257Methanal Extrusion in ipso-Substitution Reactions of Hydroxymethylindoles

Jeremy C. Dobrowolski, Kittiya Somphol, Mardi Santoso, Hung Duong, Christopher R. Gardner, Naresh Kumar and David StC. Black
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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.

Published online 28 August 2017

CH17228The Use of Imaging Mass Spectrometry to Study Peptide Toxin Distribution in Australian Sea Anemones

Michela L. Mitchell, Brett R. Hamilton, Bruno Madio, Rodrigo A. V. Morales, Gerry Q. Tonkin-Hill, Anthony T. Papenfuss, Anthony W. Purcell, Glenn F. King, Eivind A. B. Undheim and Raymond S. Norton
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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.

Published online 24 August 2017

CH17172Cobalt Species Active for Nitrous Oxide (N2O) Decomposition within a Temperature Range of 300–600°C

Naseer A. Khan, Eric M. Kennedy, Bogdan Z. Dlugogorski, Adesoji A. Adesina and Michael Stockenhuber
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Catalyst supports play a vital role in the formation of active cobalt sites for the N2O decomposition reaction. Co2+ and Co3+ are the highly active cobalt species. The acidic properties of the ZSM-5 support changes with the cobalt loading.

Published online 21 August 2017

CH17277A Novel Cancer Nanotheranostics System Based on Quantum Dots Encapsulated by a Polymer-Prodrug with Controlled Release Behaviour

Hai-Kang Huang, Jing Yan, Pei Liu, Bi-Yun Zhao, Yi Cao and Xue-Fei Zhang
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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.

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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.

Published online 14 August 2017

CH17248New Organic Acidic Cyclohexaphosphate: Synthesis, Crystal Structure, Physicochemical Study, and In Vitro Biochemical Investigation

Ramzi Fezai, Lamia Khedhiri, Hanene Hemissi, Ali Mezni and Mohamed Rzaigui
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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.

Published online 10 August 2017

CH17310Rational Design of Azo-Azomethine Receptors for Sensing of Inorganic Fluoride: Construction of Molecular Logic Gates and DFT Study

Hamid Khanmohammadi, Khatereh Rezaeian and Nafiseh Shabani
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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.

Published online 09 August 2017

CH17173Reactions of Trivalent Iodine Reagents with Classic Iridium and Rhodium Complexes

Mohammad Albayer and Jason L. Dutton
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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.

Published online 08 August 2017

CH17215Photoactive and Physical Properties of an Azobenzene-Containing Coordination Framework

James S. Caddy, Thomas B. Faust, Ian M. Walton, Jordan M. Cox, Jason B. Benedict, Marcello B. Solomon, Peter D. Southon, Cameron J. Kepert and Deanna M. D'Alessandro
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A new porous 3-dimensional coordination framework containing the novel photoactive ligand 5-((4-tert-butyl)phenylazo)isophthalic acid displays light-dependent spectroscopic properties.

Published online 08 August 2017

CH17325Star-Shaped Copolymers Based on Poly(N-vinylcaprolactam) and their Use as Nanocarriers of Methotrexate

Norma A. Cortez-Lemus and Angel Licea-Claverie
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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.

Published online 08 August 2017

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

Mehdi Rimaz, Behzad Khalili, Golaleh Khatyal, Hossein Mousavi and Farkhondeh Aali
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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.

Published online 28 July 2017

CH17272A Facile and Convenient Approach for the Synthesis of Novel Sesamol–Oxazine and Quinoline–Oxazine Hybrids

Garima Khanna, Pooja Saluja and Jitender M. Khurana
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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.

Published online 28 July 2017

CH17220Recognition of a Flavin Analogue by Novel Bile Acid-Based Receptors: Effects of Hydrogen Bonding and Aromatic π-Stacking Interactions

Pradeep Kumar Muwal, Rajesh Kumar Chhatra, Shubhajit Das and Pramod S. Pandey
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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.

Published online 25 July 2017

CH17168Alkali Metal Ion-Exchanged Zeolite X from Bamboo Leaf Biomass as Base Catalysts in Cyanoethylation of Methanol Enhanced by Non-Microwave Instant Heating

Eng-Poh Ng, Jack-Hao Chow, Siew-Fang Wong, Rino R. Mukti, Oki Muraza, Tau Chuan Ling and Ka-Lun Wong
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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.

Published online 20 July 2017

CH17206Experimental and Theoretical Investigation of the Reaction of Secondary Amines with Maleic Anhydride

Manjinder Kour, Raakhi Gupta and Raj K. Bansal
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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.

Published online 19 July 2017

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

Steven Gareth Williams, Mohan Bhadbhade, Roger Bishop and Alison Thavary Ung
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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.

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Peptide nanofibres with arginine as a building block have been prepared via a self-assembly method and decorated with Cu and Ni nanoparticles. These prepared nanostructural compounds present a unique catalytic activity for the synthesis of 5-substituted 1H-tetrazoles and the N-arylation of amines.

Published online 07 July 2017

CH17227Efficient Synthesis of an Indinavir Precursor from Biomass-Derived (–)-Levoglucosenone

Edward T. Ledingham, Kieran P. Stockton and Ben W. Greatrex
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The hydrogenated derivative of levoglucosenone was functionalised at the α-position with aldol chemistry using a series of aromatic aldehydes. The benzylidene derivative was then hydrogenated stereospecifically and the product transformed using a Baeyer–Villiger reaction into (3R,5S)-3-benzyl-5-(hydroxymethyl)-4,5-dihydrofuran-2(3H)-one, a chiral building block that can be used for the synthesis of the protease inhibitor indinavir.

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A simple and highly sensitive method for the detection of hydrogen peroxide in food samples was developed by electrodepositing Cu and MnO2 onto a g-C3N4 coated glassy carbon electrode. The sensor exhibits high selectivity, good stability, and reproducibility.

Published online 16 June 2017

CH17078Ligand-Stabilized ZnO Quantum Dots: Molecular Dynamics and Experimental Study

Rohul Hayat Adnan, Kai Lin Woon, Narong Chanlek, Hideki Nakajima and Wan Haliza Abd. Majid
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Different aminoalcohol ligands (TEA, DEA, and MEA) were found to affect the size and optical properties (band gap and emission peak) of ligand-stabilized ZnO quantum dots. Ligands of higher polarity and larger molar volume produce smaller, more monodisperse ZnO quantum dots. As the size of ZnO quantum dots decrease, the optical properties are blue-shifted.

Published online 06 June 2017

CH17060Electrophoretic Deposition of SnFe2O4–Graphene Hybrid Films as Anodes for Lithium Ion Batteries

Tao Xu, Qinghan Meng, Meng Yang, Wanyuan Zhi and Bing Cao
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SnFe2O4 has been widely used as a magnetic material or catalyst for the oxidative removal of organic pollutants, but never used as an electrode material in lithium ion batteries. In this study, binder-free SnFe2O4-rGO hybrid films with both horizontal and vertical channels were fabricated through electrophoretic deposition to present excellent electrochemical performance of lithium ion batteries.

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Heterocycles fused to quinoline frameworks widely occur in many biologically active natural products and in medicinally important drugs. Our strategy represents the first collective synthetic concise and efficient entry to nine novel condensed tetracyclic quinolinones by Friedel–Crafts cycliacylations. The simplicity and wide variability of the procedures highlights the efficiency of the methodology for constructing complex fused-ring systems.

Published online 31 May 2017

CH17203Attempted Synthesis and Unexpected β-Fragmentation of a Hindered β-Keto Nitroxide

Chris Edwards, Peter C. Healy, W. Ken Busfield, Ezio Rizzardo, San H. Thang and Ian D. Jenkins
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The attempted synthesis of a β-keto imidazolidinone nitroxide by oxidation of the β-hydroxy imidazolidinone precursor led to an unexpected ring-opening reaction. A β-fragmentation mechanism is suggested, rather than a Baeyer–Villiger rearrangement.

Published online 30 May 2017

CH17036Synthesis of Imines and Amines from Furfurals Using Continuous Flow Processing

Boris Bizet, Christian H. Hornung, Thomas M. Kohl and John Tsanaktsidis
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A simple procedure for the condensation of the bio-derived furfurals, 5-(methyl)furfural (MF) and 5-(chloromethyl)furfural (CMF), with primary amines is described. The experiments were conducted in both batch and flow conditions, with reaction times as short as 60 s. Mild reaction conditions were necessary for CMF in order to selectively react on the aldehyde and not the methyl-chlorine group.

Published online 30 May 2017

CH17194Studies on Orpiment (As2S3) Quantum Dots and their Self-Assemblies

Jinzhu Wu, Yaxiu Feng, Haishu Lin and Paul C. Ho
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Orpiment (As2S3) quantum dots (QDs) were first synthesised through top-down and bottom-up routes, and exhibit strong blue photoluminescence emission. They were effective against murine melanoma B16 cells through induction of apoptosis. Moreover, self-assemblies of orpiment QDs were fabricated by destroying the protective surface ligand layer surrounding the inner orpiment cores by addition of an acid.

Published online 29 May 2017

CH17192Synthesis, Characterisation, and Photocatalytic Behaviour of Mesoporous ZnS Nanoparticles Prepared Using By-Product Templating

Hosein B. Motejadded Emrooz, Ali R. Rahmani and Francisco J. Gotor
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In this research, relatively high surface area mesoporous ZnS nanoparticles have been synthesised using two different media. The mechanism of the by-product assisted synthesis of the prepared mesoporous ZnS nanoparticles in EtOH has been investigated using field emission scanning electron microscopy, transmission electron microscopy, powder X-ray diffraction, diffuse reflectance spectroscopy, N2 adsorption–desorption, and FT-IR spectroscopy analyses.

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