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 7 2017

CH16585Formate: A Possible Replacement for Formic Acid in Fuel Cells

Zhaoyi Yang, Yaner Wang, Ting Dong, Xiufang Yuan, Liulin Lv, Xubing Wei and Jun Wang
pp. 757-763
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Is formate an energy source? We achieve formate electrooxidation in a practical and convenient way. The precursor of the oxidation is free HCOO in fuel liquid rather than Pt-HCOOH. Formate is able to bypass the undesirable poisoning path to alternatively form carbon dioxide.

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Homologous series of 4,5-disubstituted 2H-[1,2,3]-triazole derivatives were synthesized from chalcones and sodium azide via CuI-catalyzed oxidative cycloaddition reaction in order to characterize their liquid crystalline properties by polarizing optical microscopy and differential scanning calorimetry.

CH16528Platinum(IV) Chloride Complex Ions Adsorption on Activated Carbon Organosorb 10CO

Marek Wojnicki, Ewa Rudnik, Robert P. Socha and Krzysztof Fitzner
pp. 769-775
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The recovery of platinum from acidic solutions was examined and consists of two steps. For each reaction within a step, the rate constants were determined. The first two reactions in step 1 were diffusion controlled unlike the third reaction in step 2 step, which took place at the surface of activated carbon. The results were in excellent agreement to the assumed model.

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Simultaneous temperature measurement by external and internal sensors revealed hidden inhomogeneities within the reaction mixtures of a debated microwave-assisted benzylation involving a 2-substituted pyridine reagent. Rate enhancement could be explained by macroscopic-scale localized heating in the boundary layers close to the vessel surface.

CH16600Luminescent Functionalised Supramolecular Coordination Polymers Based on an Aromatic Carboxylic Acid Ligand for Sensing Hg2+ Ions

Xiaojun Sun, Ping Yang, Guangfeng Hou, Jinzhi Wei, Xueliang Wang, Doudou Yang, Xin Zhang, Hong Dong and Fengming Zhang
pp. 786-791
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Two luminescent functionalised supramolecular coordination polymers based on an aromatic carboxylic acid ligand exhibit efficient luminescence sensing for Hg2+ ions.

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A 3D heterometal–organic framework was synthesised. The compound is 2-fold interpenetrating. It displayed good thermal and solvents stability and exhibited high sensitive and qualitative luminescent detection of nitrobenzene. The present study is the first report on the use of an interpenetrating heterometallic metal–organic framework as a luminescent probe for nitrobenzene

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The Ru2 double bond in (RuPz)2, composed of one σ bond and one π bond, is unravelled by DFT (B3LYP) and WFT (CASSCF and NEVPT2) calculations. The ground state shows a Ru–Ru distance of 2.38 Å, a stretching frequency of 202 cm-1, and a bonding energy of 30.7 kcal mol-1. This agrees with experimental results.

CH16704Novel Dual BODIPY-Carbazole Conjugates with Various Linkers

Qiao Zong, Hongbin Zhao, Weinan Zhou, Wentao Zhang, Junxu Liao and Nianfa Yang
pp. 806-815
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Four dual BODIPY-carbazole conjugates (BDPa–d) with various linkers were synthesized. The results suggest that the linkers have significant effect on the photophysical and electrochemical properties of the conjugates. The conjugates show intensive absorption, remarkable Stocks shifts, and suitable HOMO–LUMO energy levels, which are promising for photovoltaic applications.

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Cross-linked poly(acrylamide) microspheres, PAMBA, with mean diameters ranging from 169.7 to 525.2 nm were successfully prepared by dispersion polymerisation of acrylamide in an aqueous ammonium sulfate solution with N,N′-methylenebis(acrylamide) as the cross-linking agent and sodium dodecyl sulfate as the stabiliser. The mean diameter of the PAMBA microspheres can be controlled by adjusting the concentration of the stabiliser.

CH16692Shear Stress Induced Fabrication of Dandelion-Shaped Lanthanide Phosphate Nanoparticles

Nicholas J. D'Alonzo, Paul K. Eggers, Ela Eroglu and Colin L. Raston
pp. 823-829
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Lanthanide phosphate nanoparticles were produced under continuous flow in a vortex fluidic device in the presence of polyvinylpyrrolidone. Changes in the morphology of the dandelion-shaped nanoparticles were possible by varying the chain length of PVP, and the rotational speed and tilt angle of the tube in the vortex fluidic device.

CH16496DNA Photocleavage and Binding Modes of Methylene Violet 3RAX and its Derivatives: Effect of Functional Groups

Ke Yang, Xiong Zhang, Fang Yang, Fengshou Wu, Xiulan Zhang and Kai Wang
pp. 830-836
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Methylene violet 3RAX 1 and its derivatives 2–5 were synthesised and characterised. The binding mode between the synthesised compounds and DNA and their DNA photocleavage ability were investigated. The results suggest that the binding mode between methylene violet 3RAX and DNA, its ability to generate singlet oxygen, and DNA photocleavage activity could be changed through modification of the amino group on methylene violet 3RAX.

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The simultaneous α-iodination and Nβ-arylation mechanism of 5-alkyoxy-4-phenylamino-2(5H)-furanone by (diacetoxyiodo)benzene was investigated by means of density functional theory (DFT), selecting 4-(diphenylamino)-5-methoxy-3-iodo-2(5H)-furanone as the calculation model.

CH165451-(+)-Dehydroabietylimidazolium Salts as Enantiomer Discriminators for NMR Spectroscopy

H. Q. Nimal Gunaratne, Tiina Laaksonen, Kenneth R. Seddon and Kristiina Wähälä
pp. 845-856
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The determination of enantiomeric purity is frequently required in synthetic chemistry. NMR can be used for this purpose if suitable chiral solvating agents are available. Nine new (+)-dehydroabietylimidazolium salts were synthesised and used as efficient chiral solvating agents for resolving several racemic aromatic and non-aromatic carboxylate salts.

Online Early

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

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

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
 
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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.

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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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.

Published online 28 June 2017

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
 
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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.

Published online 27 June 2017

CH17208Selective Fluorescent Detection of Cysteine over Homocysteine and Glutathione by a Simple and Sensitive Probe

Yan-Fei Kang, Hai-Xia Qiao, Ya-Li Meng, Zhen-Hui Xin, Li-Ping Ge, Ming-Yan Dai, Zhang He and Cun-Hui Zhang
 
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A simple and sensitive fluorescence probe, based on a substituent coumarin as fluorophore and acrylate as recognition site, is able to selectively and quantifiably detect cysteine over other biothiols such as homocysteine and glutathione.

Published online 22 June 2017

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

Edith Chow, Devi D. Liana, Burkhard Raguse and J. Justin Gooding
 
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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.

Published online 21 June 2017

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
 
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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.

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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

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
 
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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.

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.

Published online 25 May 2017

CH17004Ionic Liquid–Liquid Separations Using Countercurrent Chromatography: A New General-Purpose Separation Methodology

Leslie Brown, Martyn J. Earle, Manuela A. Gîlea, Natalia V. Plechkova and Kenneth R. Seddon
 
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A custom-designed liquid–liquid countercurrent chromatographic instrument (above left), based on the J-type centrifuge, in which at least one phase contains an ionic liquid, is capable of the separation of inorganic (above right), organic, or bio-based materials on the 0.1–10 g scale.

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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.

Published online 23 May 2017

CH16720A Novel Eco-Friendly Scale and Corrosion Inhibitor Modified by β-Cyclodextrin

Mingjin Tang, Jianbo Li, Zhengrong Ye, Zimin Kou and Luoping Fu
 
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A polymer, β-MEA, was synthesised from β-cyclodextrin (β-CD), 3-chloro-2-methylpropene (MAC), epoxysuccinic acid (ESA), and 2-acrylamido-2-methyl propane sulfonic acid (AMPS). Its structure, molecular weight, thermal stability, inhibition performance, and mechanism were investigated. The results showed that β-MEA achieves better scale and corrosion inhibition efficiencies compared with poly(aspartic acid) (PASP).

Published online 19 May 2017

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
 
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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 novel series of 3D LnIII–CuI heterometallic coordination polymers {[Ln2Cu4I3(ina)7(DMA)2]n·nDMA were synthesised by a solvothermal reaction, comprising of inorganic Cu4I3 clusters linked by Ln2(ina)7(DMA) rod units. The luminescent properties of partial compounds have been investigated in detail.

Published online 01 May 2017

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
 
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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.

Published online 18 April 2017

CH17056Tunable Electromagnetic Enhancement of Gold Nanoparticle Arrays

Hailiang Huang, Guobin Yi, Xihong Zu, Benbin Zhong, Wenjing Lin, Minghai Zhang and Hongsheng Luo
 
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The fluorescence and Raman intensity of poly(3-hexylthiophene) (P3HT)-coated gold nanoparticle arrays with different particle sizes and interparticle distances were enhanced in comparison with pristine P3HT due to electromagnetic field enhancement based on localised surface plasmon resonance (LSPR). The fluorescence and Raman signals of P3HT on gold nanoparticle arrays were gradually enhanced with increasing nanoparticle diameter/interparticle distance ratio.

Published online 13 April 2017

CH17038Enhancing the Magnetic–Luminescent Properties of Fe3O4@Y2O3:Eu3+ Core–Shell Bifunctional Particles Using Li+ Doping

Hong Zhang, Le Wang, Tuo Wu, Rubiao Chen, Dong Luo and Yanghui Li
 
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Bifunctional magnetic–luminescent Fe3O4@Y2O3:Eu3+, Li+ composite particles were prepared with Y2O3 co-doped with Eu3+ and Li+ ions as a shell to enhance their luminescence intensity and saturation magnetisation through a urea homogeneous precipitation method.

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The photocatalytic reaction of prepared Bi2WO6/g-C3N4 composite materials followed a direct solid-state Z-scheme mechanism, which facilitated charge transfer and effectively reduces the recombination of photoinduced electrons and holes, resulting in an enhanced photodegradation efficiency under visible light irradiation.

Published online 05 April 2017

CH16694Synthesis of Self-Assembled Co3O4 Nanoparticles with Porous Sea Urchin-Like Morphology and their Catalytic and Electrochemical Applications

Saba Jamil, Muhammad Ramzan Saeed Ashraf Janjua and Shanza Rauf Khan
 
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Unique self-assembled nanoparticles with sea urchin-like pointed edges were synthesized by a solvothermal approach. The high value of the apparent rate constant, kapp, is due to the unique morphology of the Co3O4 nanoparticles.

Published online 03 April 2017

CH17064Influence of Adsorbent Nature on the Dynamic Headspace Study of Insect Semiochemicals

Sergio A. Rodriguez, María L. Paliza and Monica A. Nazareno
 
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Different adsorbents (Tenax TA, Porapak Q, and Hayesep Q, among others) were evaluated in a headspace dynamic system containing a mixture of insect semiochemicals. The results demonstrated that Porapak Q and Porapak Rxn RP were able to produce similar ratios of compounds to that of a standard solution with the highest recovery yields.

Published online 03 March 2017

CH16383The History of Azulenyl Squaraines

Daniel E. Lynch and Darren G. Hamilton
 
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The first azulenyl squaraine dye was reported in 1966, but little activity in the scientific literature has given the impression that they remain unexplored. However, much has been recorded in the patent literature and it is the purpose of this review to bring this record to the attention of researchers.

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