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 8 2017

CH16383The History of Azulenyl Squaraines

Daniel E. Lynch and Darren G. Hamilton
pp. 857-871
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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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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.

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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.

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

Sergio A. Rodriguez, María L. Paliza and Monica A. Nazareno
pp. 902-907
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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.

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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.

CH17056Tunable Electromagnetic Enhancement of Gold Nanoparticle Arrays

Hailiang Huang, Guobin Yi, Xihong Zu, Benbin Zhong, Wenjing Lin, Minghai Zhang and Hongsheng Luo
pp. 917-922
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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.

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
pp. 923-932
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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.

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

Mingjin Tang, Jianbo Li, Zhengrong Ye, Zimin Kou and Luoping Fu
pp. 933-942
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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).

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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.

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
pp. 952-956
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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.

Online Early

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

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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.

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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.

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 03 August 2017

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
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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.

Published online 02 August 2017

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
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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.

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

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 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.

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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 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.

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.

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