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 6 2017

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1,2-Diaryl-1,2-disodioethanes are easily prepared, versatile, and tunable diorganometals finding application in 1,2-reductive eliminations as well as in the degradation of several persistent organic pollutants as homogeneous synthetic equivalents of a highly reactive form of Na metal. Further applications as dinucleophiles and bases are also described.

CH16459Synthesis of a Tetraphenylethene-Substituted Tetrapyridinium Salt with Multifunctionality: Mechanochromism, Cancer Cell Imaging, and DNA Marking

Anushri Rananaware, Amanda N. Abraham, Duong Duc La, Vishal Mistry, Ravi Shukla and Sheshanath V. Bhosale
pp. 652-659
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A tetrapyridyl-substituted tetraphenylethylene (TPy-TPE) works as a good fluorescent visualiser for specific staining for cellular imaging and as a DNA marker.

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Several indeno[1,2-c]pyridazines were efficiently synthesised using the one-pot, three-component reaction of substituted indanones, arylglyoxalmonohydrates, and hydrazine in the presence of 1,5-diazabicyclo[4,3,0]non-5-ene (DBN) in water at room temperature.

CH16288Preparation and Characterization of PA6-PEG/Li High Performance Static Dissipation Composites

Chongling Yang, Shouzai Tan, Gengen Chen and Litao Guan
pp. 669-676
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A series of novel PA6-PEG/Li composites were developed by melt blending the PA6-PEG copolymer (10 wt-% PEG) with three different kinds of colourless lithium salts (LiCl, C18H35LiO2, LiAc). The PA6-PEG/LiCl composite showed an excellent static dissipation performance of 2.71 × 108 Ω square–1.

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The fluorescence intensity of CB[7]–PAL, CB[7]–BER, or CB[7]–COP system decreased with increasing amounts of oxaliplatin (l-OHP) added. The trend is attributed to the competition between l-OHP and PAL, BER, or COP molecules for occupancy of the CB[7] cavity.

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Cope rearrangement of bicycle[5.1.0]octa-2,5-diene and its 8-hetero- (N,O,P) and 4,8-dihetero-analogues has been investigated in the gas phase at the B3LYP/6-31+G* level. The results reveal that relative stabilities of the three-membered ring undergoing opening and the three-membered ring being formed as a result of the Cope rearrangement determine the feasibility and rate of the rearrangement.

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Hierarchical HZSM-5 were synthesised by controlled desilication in alkaline medium and used as catalyst for the selective oxidation of 2,3,6-trimethylphenol to 2,3,5-trimethyl-1,4-benzoquinone. The combined studies suggested that the nature of the solvent, intrinsic acidity, and shape selectivity of the hierarchical structure ensured high catalytic properties.

CH16224Open-Chain Crown-Ether-Derived Two-Photon Fluorescence Probe for Real-Time Dynamic Biopsy of Mercury Ions

Chibao Huang, Daohai Zhang, Junle Qu, Xiaonan Liu, Guanglian Zhao, Tingxiang Yuan and Yang Liu
pp. 705-711
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The probe developed in the present study can selectively detect Hg2+ ions in live cells and living tissues without interference from other metal ions and the membrane-bound probes, and its quenching constant is 8.73 × 105 M–1.

CH16357Ring-Opening Dispersion Polymerization of ʟ-Lactide with Polylactide Stabilizer in Supercritical Carbon Dioxide

Jinjun Deng, Shiping Zhan, Jingchang Wang, Zhijun Liu and Zhiyi Li
pp. 712-717
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The particle diameter distributions of PLLA show that the stabilizer S131 with short lipophilic segment could improve the particle diameter distribution range, compared with the long lipophilic segment of stabilizer S121. With increasing concentration of the stabilizer S131, the particle size decreased and particle distribution became narrow.

CH16562Aptamer-Based Fluorescent Switch for Sensitive Detection of Oxytetracycline

Mahsa Babaei, Seyed Hamid Jalalian, Hadi Bakhtiari, Mohammad Ramezani, Khalil Abnous and Seyed Mohammad Taghdisi
pp. 718-723
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In this paper, we introduce a novel aptasensor for fast detection of oxytetracycline (OTC), based on a triple helix molecular switch (THMS) complex formation. The limit of detection (LOD) of this sensor was 1.67 and 6.44 nM in phosphate buffer and milk samples, respectively. The sensor also showed a high selectivity towards OTC.

CH16537Dehydrogenative Coupling of Hydrosilanes and Alcohols by Alkali Metal Catalysts for Facile Synthesis of Silyl Ethers

Adimulam Harinath, Jayeeta Bhattacharjee, Srinivas Anga and Tarun K. Panda
pp. 724-730
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The RO–H/H–Si cross-dehydrogenative coupling (CDC) of alcohols and hydrosilanes with high yield (up to 99 %) and chemoselectivity for the production of silyl ethers using alkali metal salts [MN(SiMe3)2] (M = Li, Na, K) as pre-catalysts and under ambient conditions is presented.

CH16554Effective Dissolution of Biomass in Ionic Liquids by Irradiation of Non-Thermal Atmospheric Pressure Plasma

Kosuke Kuroda, Kai Shimomura, Tatsuo Ishijima, Kenji Takada, Kazuaki Ninomiya and Kenji Takahashi
pp. 731-734
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Lignocellulose has gained much interest as a potential renewable energy resource. However, it is hardly soluble. In this study, a non-thermal plasma was applied to dissolution of lignocellulose to ionic liquids. Chemically active species, which were generated by the plasma, induced decomposition of the lignin network, and consequently dissolution of biomass into ionic liquids was accelerated.

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Degradable polyanhydride-based nanoparticles are synthesized using thiol–ene ‘click’ polymerization followed by emulsification and solvent evaporation. These nanoparticles have tuneable degradation times, can be easily functionalized, and encapsulate payloads that can then be released upon degradation. Such degradable polymer nanoparticles have potential in many nano/bio-theranostic applications.

CH16455Ilimaquinone and 5-epi-Ilimaquinone: Beyond a Simple Diastereomeric Ratio, Biosynthetic Considerations from NMR-Based Analysis

Asmaa Boufridi, David Lachkar, Dirk Erpenbeck, Mehdi A. Beniddir, Laurent Evanno, Sylvain Petek, Cécile Debitus and Erwan Poupon
pp. 743-750
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Ilimaquinone is a biologically active sesquiterpene isolated from Dactylospongia sponges. An intriguing diastereomeric ratio is observed based on an impressive collection of samples. Biosynthetic and ecological considerations stem from this study.

CH16667Rates of Water Exchange in 2,2′-Bipyridine and 1,10-Phenanthroline Complexes of CoII and MnII

Shravan S. Acharya, Bjorn Winther-Jensen, Leone Spiccia and C. André Ohlin
pp. 751-754
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The catalytically and geochemically relevant rates of water exchange of four new CoII and one new MnII 2,2′-bipyridine and 1,10-phenanthroline complexes have been determined using the temperature-dependent line broadening of the 17O NMR signal from the solvent water.

Online Early

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

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 10 March 2017

CH16616A Combined Experimental and Theoretical Study on the Reaction Mechanism and Molecular Structure of 4-(Diphenylamino)-3-iodo-2(5H)-furanone

Xiumei Song, Fuling Xue, Zongcai Feng, Yun Wang, Zhaoyang Wang and Yanli Xi
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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.

Published online 08 March 2017

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

H. Q. Nimal Gunaratne, Tiina Laaksonen, Kenneth R. Seddon and Kristiina Wähälä
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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.

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.

Published online 27 February 2017

CH16704Novel Dual BODIPY-Carbazole Conjugates with Various Linkers

Qiao Zong, Hongbin Zhao, Weinan Zhou, Wentao Zhang, Junxu Liao and Nianfa Yang
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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.

Published online 20 February 2017

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
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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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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.

Published online 13 February 2017

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
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Two luminescent functionalised supramolecular coordination polymers based on an aromatic carboxylic acid ligand exhibit efficient luminescence sensing for Hg2+ ions.

Published online 13 February 2017

CH16656A Novel, Interpenetrating Metal–Organic Framework: Synthesis, Structure, and Luminescence Detection of Nitrobenzene

Peng-Fei Shi, Li-Xian Wang and Zhao-Peng Yu
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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

Published online 10 February 2017

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

Marek Wojnicki, Ewa Rudnik, Robert P. Socha and Krzysztof Fitzner
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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.

Published online 09 February 2017

CH16692Shear Stress Induced Fabrication of Dandelion-Shaped Lanthanide Phosphate Nanoparticles

Nicholas J. D'Alonzo, Paul K. Eggers, Ela Eroglu and Colin L. Raston
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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.

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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.

Published online 08 February 2017

CH16643Investigation of Selective Microwave Heating Phenomena in the Reactions of 2-Substituted Pyridines

Péter Bana and István Greiner
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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.

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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.

Published online 06 January 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
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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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