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 1 2017

CH16241The Use of Hydrogels as Biomimetic Materials for 3D Cell Cultures

Eric Y. Du, Adam D. Martin, Celine Heu and Pall Thordarson
pp. 1-8
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Hydrogels have been gaining increasing popularity as biomimetic materials for their unique properties such as high water content, ease of functionalisation, and high biocompatibility. This highlight article describes the recent developments of hydrogels, with a large focus on the supramolecular variants, in their application for 3D cell cultures.

CH16088Patterned Copper Sulfide Thin Films: a Method for Studying Leaching Behaviour

Rachel S. Brokenshire, Anthony Somers, Miao Chen and Angel A. J. Torriero
pp. 26-32
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This work presents a practical and simple alternative method for studying the leaching of copper from copper sulfide. It is demonstrated, for the first time, that micro-patterned thin films can be used as a model system for studying mineral leaching of copper-bearing minerals directly by measuring changes in the film thickness using white light interferometric profilometry and changes in the film morphology and elemental composition using scanning electron microscopy coupled with energy-dispersive X-ray spectroscopy.

CH16126Direct Synthesis of Nitriles from Aldehydes and Hydroxylamine Hydrochloride Catalyzed by a HAP@AEPH2-SO3H Nanocatalyst

Samane Memar Masjed, Batool Akhlaghinia, Monireh Zarghani and Nasrin Razavi
pp. 33-43
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We describe an efficient method for the direct preparation of nitriles from aldehydes and hydroxylamine hydrochloride catalyzed by sulfonated nanohydroxyapatite functionalized by 2-aminoethyl dihydrogen phosphate (HAP@AEPH2-SO3H) as an eco-friendly and recyclable solid acid nanocatalyst.

CH16213Mo(CO)6 as a Solid CO Source in the Synthesis of Aryl/Heteroaryl Weinreb Amides under Microwave-Enhanced Condition

Raghu Ningegowda, Savitha Bhaskaran, Ayyiliath M. Sajith, Chandrashekar Aswathanarayanappa, M. Syed Ali Padusha, Nanjunda Swamy Shivananju and Babu Shubha Priya
pp. 44-51
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The facile transformation of aryl/heteroaryl nonaflates into corresponding amides via Pd-catalyzed aminocarbonylation using Mo(CO)6 as a solid CO source under microwave-enhanced condition is reported. The method was found to be tolerant with respect to a diverse range of electronically biased aryl/heteroaryl nonaflates, and exceptional yields were obtained. The optimized protocol was further extended to a diverse range of amines.

CH16127Self-Assembly of an Amphiphilic OEG-Linked Glutamide Lipid

Shuo Wang, Youguo Zhang, Qiang Li, Rongqin Sun, Lin Ma and Liangchun Li
pp. 52-60
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Amphiphilic peptides with or without oligoethylene glycol (OEG) chains based on 3,4-bis(benzyloxy)benzoic-linked glutamide were designed and their self-assembly was investigated. The studies showed that the amphiphilic peptide 3 with OEG chains could not only form stable gels in a wide range of solvents, but also allowed control of the width of nanofibres in the gel formed with changing water content.

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The generalized anomeric relationships in halocarbonyl isocyanates (13) and halocarbonyl azides (46) result from the cooperative effects of the hyperconjugative generalized anomeric effects (HC-GAE) and Pauli exchange-type repulsion (PETR). The electrostatic model associated with the dipole–dipole interactions (EM-DDI) and the attractive electrostatic interactions (AEIs) between the natural atomic charges have no significant effects on the conformational preferences in compounds 13 and 46.

CH16228Rheopectic Gel Formation of Stimuli-Responsive Ionic Liquid/Water Mixtures

Yukinobu Fukaya, Takuro Nakano and Hiroyuki Ohno
pp. 74-78
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Ionic liquids are composed of ions only. However, they are not always completely soluble in water. Mixtures of phosphonium/phosphonate-type ionic liquids and water prepared herein exhibited stimuli-responsive phase transition, lower critical solution temperature phase transition, and thermoreversible viscosity change, and underwent rheopectic gelation depending on the water content

CH16321Organometallic Complexes for Non-Linear Optics. 59. Syntheses and Optical Properties of Some Octupolar (N-Heterocyclic Carbene)gold Complexes

Gang Liu, Cristóbal Quintana, Genmiao Wang, Mahesh S. Kodikara, Jun Du, Rob Stranger, Chi Zhang, Marie P. Cifuentes and Mark G. Humphrey
pp. 79-89
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The nonlinear optical (NLO) coefficients of (triphenylphosphine)gold alkynyl complexes are better than those of (N-heterocyclic carbene)gold alkynyl complexes; calculations suggest that the key low-energy transitions are from the (phosphine)gold to the alkynyl ligand in the former, and from the Au-alkynyl group to NHC in the latter.

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This work involves the experimental and theoretical study of the nucleophilic substitution of meta- and para-substituted benzyl bromides with benzylamine.

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The kinetics of the nucleophilic substitution reactions of bis(N,N-diethylamino)phosphinic chloride with XC6H4NH2(D)2 are investigated in MeCN at 65.0°C. This study examines the substituent effects, deuterium kinetic isotope effects (DKIEs), and mechanism of the phosphoryl transfer reactions. A concerted SN2 mechanism involving the predominant backside attack is proposed.

CH16214Al2O3 Microspheres Prepared by Cathode Plasma Electrolysis

Chenxu Liu, Jin Zhang, Yedong He, Peng Wang, Shunjie Deng and Shuguang Zhang
pp. 120-124
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Al2O3 microspheres were prepared by cathode plasma electrolysis without additional heating treatment. The microspheres, with diameters of 5–30 μm, consisted of γ-Al2O3 and α-Al2O3. The mechanism and model were put forward in the formation process.

Online Early

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

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An N-heterocyclic carbene catalysed Mukaiyama–Michael addition between several TMS enol ethers and chalcone derivatives has been discovered. Also the related dehydrative Mukaiyama aldol followed by a Mukaiyama–Michael addition process has been developed. The enantioselective variant of these reactions has been examined with homochiral catalysts, which are active but fail to achieve enantioinduction.

Published online 18 January 2017

CH16609Study on the Acid-Induced Ring-Expansion of an Oxaphosphirane Complex with an Electron-Withdrawing C-Substituent

Cristina Murcia García, Gregor Schnakenburg and Rainer Streubel
 
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A study on the acid-induced ring-expansion reaction of the first oxaphosphirane complex bearing C6F5 as an electron-withdrawing C-substituent using trifluoromethanesulfonic acid and electronically different aldehydes is described. The stereoselectively obtained 1,3,4-dioxaphospholane complexes 4ac were unambiguously characterized by elemental analysis, multinuclear NMR, mass spectrometry, and single crystal X-ray diffraction studies.

Published online 11 January 2017

CH16614Synthetic Models for Nickel–Iron Hydrogenase Featuring Redox-Active Ligands

David Schilter, Danielle L. Gray, Amy L. Fuller and Thomas B. Rauchfuss
 
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Nickel–iron hydrogenases produce and consume hydrogen using elaborate electron and proton transport machinery. Although synthetic modelling of nickel–iron hydrogenases has developed rapidly, it has largely ignored aspects of substrate transfer. Reported here are nickel–iron mimics bearing redox-active ferrocenyl ligands, these trinuclear systems representing advanced models of the native enyzmes.

Published online 09 January 2017

CH16565Weak Intermolecular Forces, but High Melting Points

Jiabin Gao, Djamal Djaidi, Christopher E. Marjo, Mohan M. Bhadbhade, Alison T. Ung and Roger Bishop
 
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Racemic 4 melts above 350°C despite its low molar mass and absence of Pauling hydrogen bonding. X-Ray and Hirshfeld surface analyses reveal excellent complementarity between homochiral molecules of 4, and layers of opposite handedness are linked by the aza-1,3-peri hydrogen interaction. Weak intermolecular forces are discussed in context of the Lipinski ‘rule of 5’ solubility criteria.

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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 09 January 2017

CH16602Hydroxyl Radicals via Collision-Induced Dissociation of Trimethylammonium Benzyl Alcohols

Peter W. Moore, Jordan P. Hooker, Athanasios Zavras, George N. Khairallah, Elizabeth H. Krenske, Paul V. Bernhardt, Gina Quach, Evan G. Moore, Richard A. J. O'Hair and Craig M. Williams
 
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Arguably the most famous of all small molecule reactive intermediates is the hydroxyl radical. Methods to generate hydroxyl radicals from organic precursors are rare, with only one known example for the solution phase. Mass spectrometry is a key identifying technique is this area, and reported herein are new HO and DO radical precursors based on the trimethylammonium benzyl alcohol motif.

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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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.

Published online 03 January 2017

CH16580Brønsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes

Ciputra Tejo, Davin Tirtorahardjo, David Philip Day, Dik-Lung Ma, Chung-Hang Leung and Philip Wai Hong Chan
 
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A Brønsted base-mediated method for the synthesis of α,α-diacylaziridines and α,α,β-triacylaziridines from reaction of 2-alkyl-substituted-1,3-dicarbonyl compounds and 2-acyl-substituted-1,4-dicarbonyl compounds with arylsulfonyliminoiodinanes (ArSO2N=IPh) under atmospheric conditions is described.

Published online 23 December 2016

CH16659Fluorescent Ion Efflux Screening Assay for Determining Membrane-Active Peptides

Neil M. O'Brien-Simpson, Wenyi Li, Namfon Pantarat, Mohammed Akhter Hossain, Frances Separovic, John D. Wade and Eric C. Reynolds
 
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The emergence of antibiotic-resistant microbes and the lack of new antibiotics require development of new antimicrobial molecules and screening assays for them. We provide a proof of concept that a large unilamellar vesicle method used to study chloride ion efflux can be adapted to identify membrane-active antimicrobial peptides and screen their relative activity.

Published online 23 December 2016

CH16587Syntheses, Structural Studies, and Copper Iodide Complexes of Macrocycles Derived from Williamson Ether Syntheses Involving 2,9-Bis(4-hydroxyphenyl)-1,10-phenanthroline, α,ω-Dibromides, and Resorcinol or 2,7-Dihydroxynaphthalene

Zuzana Baranová, Hashem Amini, Madhav Neupane, Sydney C. Garrett, Andreas Ehnbom, Nattamai Bhuvanesh, Joseph H. Reibenspies and John A. Gladysz
 
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The title macrocycles were assembled by first combining the grey and maroon building blocks, followed by a condensation with 1. The CuI moieties were markedly removed from the 1,10-phenanthroline planes, as represented by the basketball above the basket rim, and voids in the crystals were analyzed in the context of rotaxane formation.

Published online 21 December 2016

CH16591Alpha Helix Nucleation by a Simple Cyclic Tetrapeptide

Huy N. Hoang, Chongyang Wu, Renee L. Beyer, Timothy A. Hill and David P. Fairlie
 
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The simple cyclic tetrapeptide cyclo-(1,4)-[Ala-Arg-Ala-homoGlu]-NH2 (3) is shown to adopt an unusual α-turn structure. The latter structure is not α-helical but can nucleate α-helicity when attached to the N-terminus of either model peptides or two biologically relevant peptides. This new N-terminal helix-capping macrocycle provides simple and rapid synthetic access to α-helical peptide structures.

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The presence of nucleophilic substituents neighbouring a ketone functional group switches the character of the lowest triplet excited states from (π,π*) or (n,π*) to (σ*,π*).

Published online 20 December 2016

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
 
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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.

Published online 16 December 2016

CH16552Supramolecular Assemblies of Cucurbit[10]uril Based on Outer Surface Interactions

Yu-Qing Yao, Qing Liu, Ying Huang, Qian-Jiang Zhu, Yun-Qian Zhang, Xin Xiao, Zhu Tao and Gang Wei
 
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Two Q[10]-based supramolecular assemblies were prepared via different approaches, and these Q[10]-based supramolecular assemblies possess porous features that suggest that Q[n]-based compounds could be used to manufacture molecular sieves and sensors and applied in absorption and separation technologies

Published online 14 December 2016

CH16556Molecular Assemblies and Spin-Crossover Behaviour of Cobalt(ɪɪ) Complexes with Terpyridine Incorporating Different Nitrogen Positions in Pyridine Rings

Risa Nakahara, Manabu Nakaya, Jong Won Shin, Ryo Ohtani, Masaaki Nakamura and Shinya Hayami
 
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Cobalt(ii) complexes with terpyridine-type ligands, [Co(n-pyterpy)2](ClO4)2 (n = 3 (1), 4 (2)), show different molecular assemblies depending on the nitrogen position in the pyridine substituent. The cooperativity estimated from the magnetic behaviour reflects their assembly nature.

Published online 14 December 2016

CH16577Crystal Structure of a Heterometallic Luminophore: The RuII Complex of a Ferrocenyl-Terpyridine with a Flexible Linkage

Young Hoon Lee, Jong Won Shin, Yusuke Sekimoto, Shinya Hayami, Jack Harrowfield and Yang Kim
 
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Crystal structure determination on the mixed ligand complex [Ru(tpy)(L1)](ClO4)2 (tpy = 2,2′:6′,2″-terpyridine; L1 = 4′-(ferrocenylmethylaminomethylphenyl)terpyridine) shows the ferrocenyl group to be located as remotely as possible from the RuII centre. This may explain the fact that emission from the RuII centre is detectable even at room temperature in solution.

Published online 14 December 2016

CH16492Evaluation of Methanol Induced Free Radicals in Mice Liver

Lifang Zhou, Hongli Zhao, Tieying Pan, Adrian Trinchi, Minbo Lan and Gang Wei
 
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In this work, oxidative stress (OS) models of methanol in mice were successfully established. The experimental results clearly demonstrated that methanol could stimulate the production of hydroxyl radicals in the liver of mice to induce OS. Rhubarb and vitamin C were found to have a protective effect on the liver of mice under acute OS.

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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.

Published online 12 December 2016

CH16626Total Solid-Phase Synthesis of Biologically Active Drosophila Insulin-Like Peptide 2 (DILP2)

Feng Lin, Mohammed Akhter Hossain, Stephanie Post, Galina Karashchuk, Marc Tatar, Pierre De Meyts and John D. Wade
 
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The fruit fly insulin-like peptide 2, DILP2, is one of seven closely related peptides that each act upon the same insulin-like receptor. It was successfully chemically assembled by regioselective disulfide bond formation within its two synthetic chains and shown to potently stimulate receptor phosphorylation and downstream signalling.

Published online 09 December 2016

CH16559Synthesis of Norfijimycin A with Activity against Mycobacterium tuberculosis

Alexander Stoye, Gayathri Nagalingam, Warwick J. Britton and Richard J. Payne
 
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Fijimycin A is a cyclic depsipeptide that has been shown to possess activity against a range of pathogenic bacteria. This communication describes the total synthesis of norfijimycin A, a simplified analogue of the marine natural product fijimycin A. The natural product analogue was shown to possess significant activity against Mycobacterium tuberculosis, the etiological agent of tuberculosis.

Published online 30 November 2016

CH16584Structural Systematics for Lanthanide(III) Systems: Interactions of the Achiral Hexamminecobalt(III) Cation with Tris(dipicolinato)lanthanate(III) Anions

Jack M. Harrowfield, Irene Ling, Brian W. Skelton, Alexandre N. Sobolev and Allan H. White
 
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Structures of [Co(NH3)6][Ln(dipic)3] hydrates have been analysed in terms of the weak interactions occurring between the achiral cation and the chiral anions.

Published online 29 November 2016

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
 
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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.

Published online 25 November 2016

CH16510Molecular Insights into the Interaction Between the SPRY Domain-Containing SOCS Box Protein SPSB2 and Peptides Based on the Binding Motif from iNOS

Eleanor W. W. Leung, Mark D. Mulcair, Beow Keat Yap, Sandra E. Nicholson, Martin J. Scanlon and Raymond S. Norton
 
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Surface plasmon resonance and NMR spectroscopy were used to gain insights into the binding of iNOS-derived peptides to SPSB2. The complex interplay of peptide sequence and protein binding will inform efforts to design peptide therapeutics to disrupt the iNOS–SPSB interaction.

Published online 25 November 2016

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
 
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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.

Published online 24 November 2016

CH16589Synthesis and Protein Engineering Applications of Cyclotides

Haiou Qu, Bronwyn J. Smithies, Thomas Durek and David J. Craik
 
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Cyclotides are a group of cysteine-rich peptides derived from plants. Their exceptional stability based on their head-to-tail cyclized backbone and cystine knot, together with their tolerance to sequence modifications, make them promising drug design scaffolds into which novel bioactive sequences may be grafted. These grafting applications are achievable by solid-phase peptide synthesis. This article describes recent developments in the chemical synthesis and enzyme-mediated cyclization of cyclotides.

Published online 16 November 2016

CH16562Aptamer-Based Fluorescent Switch for Sensitive Detection of Oxytetracycline

Mahsa Babaei, Seyed Hamid Jalalian, Hadi Bakhtiari, Mohammad Ramezani, Khalil Abnous and Seyed Mohammad Taghdisi
 
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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.

Published online 15 November 2016

CH16547Synthesis and Structures of Rare Earth 3-(4?-Methylbenzoyl)-propanoate Complexes – New Corrosion Inhibitors

Caspar N. de Bruin-Dickason, Glen. B. Deacon, Craig M. Forsyth, Schirin Hanf, Oliver B. Heilmann, Bruce R. W. Hinton, Peter C. Junk, Anthony E. Somers, Yu Qing Tan and David R. Turner
 
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A series of rare earth (RE) 3-(4′-methylbenzoyl)propanoate (mbp) complexes [RE(mbp)3(H2O)] (RE = Y, La, Ce, Nd, Ho, Er) have been prepared by either metathesis reactions between the corresponding rare earth chloride and Na(mbp) or protolysis of rare earth acetates by the free acid.

Published online 14 November 2016

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
 
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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.

Published online 10 November 2016

CH16532Macrocyclic Peptidomimetics Prepared by Ring-Closing Metathesis and Azide–Alkyne Cycloaddition

Ashok D. Pehere, Xiaozhou Zhang and Andrew D. Abell
 
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Ring-closing metathesis (RCM) and copper(i)-catalyzed azide–alkyne cycloaddition (CuAAC) are powerful strategies to introducing a macrocycle. This review focusses on the current synthetic approaches to access biologically active macrocycles that target important therapeutic aims for conditions such as cancer, cataracts, HIV, and neurological diseases.

Published online 09 November 2016

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
 
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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.

Published online 07 November 2016

CH16501Synthesis of Multicomponent Peptide-Based Vaccine Candidates against Group A Streptococcus

Waleed M. Hussein, Jiaxin Xu, Pavla Simerska and Istvan Toth
 
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A stepwise conjugation technique was employed to synthesise a multiantigenic vaccine candidate against Group A streptococcus (GAS) through azide–alkyne cycloaddition and mercapto–maleimide reactions. The final vaccine candidate consists of four different components: two GAS antigens, a T-helper epitope, and the lipidic moiety dipalmitoyl serine (DPS).

Published online 04 November 2016

CH16460Improved Extraction Yield of Citral from Lemon Myrtle Using a Cellulose-Dissolving Ionic Liquid

Koki Munakata, Masahiro Yoshizawa-Fujita, Masahiro Rikukawa and Toyonobu Usuki
 
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The extraction yield of citral from lemon myrtle using cellulose-dissolving ionic liquids was up to 2.1 times higher than that obtained using ethanol. The ionic liquid could be recycled and reused nine times for the extraction of citral.

Published online 04 November 2016

CH16527Coordination Behaviour of 1-(4,2′:6′,4′′-terpyridin-4′-yl)ferrocene and 1-(3,2′:6′,3′′-terpyridin-4′-yl)ferrocene: Predictable and Unpredictable Assembly Algorithms

Y. Maximilian Klein, Alessandro Prescimone, Edwin C. Constable and Catherine E. Housecroft
 
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1-(4,2′:6′,4″-Terpyridin-4′-yl)ferrocene offers a fixed V-shaped N,N″-donor set, but this does not lead to a predictable assembly algorithm; polymer and metalloamacrocycle formations compete. Similar competitive behaviour is observed in coordination assemblies based on 1-(4,2′:6′,4″-terpyridin-4′-yl)ferrocene, with the greater conformational flexibility of the latter adding to the non-predictability of the assembly process.

Published online 04 November 2016

CH16511Unique Functional Materials Derived from β-Amino Acid Oligomers

Mark P. Del Borgo, Ketav Kulkarni and Marie-Isabel Aguilar
 
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As demonstrated in the recent literature, β-peptides can self-assemble into a range of materials. This highlight explores recent developments in the preparation of functional materials involving β-peptides, wherein the self-assembly of β-peptides is unperturbed by side chain functionalisation and leads to the formation of stable gels and scaffolds that can support cellular growth.

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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.

Published online 28 October 2016

CH16499An Efficient Chemical Synthesis of Lassomycin Enabled by an On-Resin Lactamisation–Off-Resin Methanolysis Strategy and Preparation of Chemical Variants

Paul W. R. Harris, Gregory M. Cook, Ivanhoe K. H. Leung and Margaret A. Brimble
 
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Lasso peptides contain a unique 3-D topography (known as a lariat knot) and are touted as novel scaffolds for biomedical applications. The synthesis of the non-threaded lasso peptide lassomycin was accomplished by solid-phase peptide chemistry and a novel way to install the C-terminal ester on the fully unprotected peptide.

Published online 26 October 2016

CH16347Synthesis and Evaluation of a Biocompatible Macromolecular Gadolinium Compound as a Liver-Specific Contrast Agent for MRI

Youyang Zhan, Rong Xue, Mengchao Zhang, Chuanling Wan, Xiaojing Li, Fengkui Pei, Changjiang Sun and Lin Liu
 
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Gadolinium complexes are widely applied as magnetic resonance imaging contrast agents. However, they have some undesirable properties, e.g. low relaxivity and target non-specificity. A new biocompatible macromolecular gadolinium compound has been synthesised as a liver-specific contrast agent. The ability to improve the imaging signal and the T1-relaxivity is satisfactory, and it has a long window imaging time with a low acute toxicity.

Published online 24 October 2016

CH16488Cope Rearrangement in Bicyclo[5.1.0]octa-2,5-diene and its Mono- and Di-Hetero Analogues: A DFT Study

Priya Yadav, Shilpa Yadav, Asha Gurjar and Raj K. Bansal
 
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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.

Published online 21 October 2016

CH16398A New Fluorometric Method for the Determination of Oxaliplatin Based on Cucurbit[7]uril Supramolecular Interaction

YinXia Chang, XueChao Duan, XiangMei Zhang, Fan Liu and LiMing Du
 
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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.

Published online 20 October 2016

CH16406A Quantum Theory of Atoms-in-Molecules Perspective and DFT Study of Two Natural Products: Trans-Communic Acid and Imbricatolic Acid

Sarvesh Kumar Pandey, Mohammad Faheem Khan, Shikha Awasthi, Reetu Sangwan and Sudha Jain
 
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Intramolecular H···H as well as C···H non-covalent interactions have been retrieved and characterized using quantum theory of atoms-in-molecules and the computed chemical reactivity index using HOMO–LUMO gap and molecular electrostatic potential surface have been compared with experimentally observed bioactivity parameter.

Published online 19 October 2016

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

Chongling Yang, Shouzai Tan, Gengen Chen and Litao Guan
 
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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.

Published online 17 October 2016

CH16407Synthesis of Multivalent [Lys8]-Oxytocin Dendrimers that Inhibit Visceral Nociceptive Responses

Jingjing Wan, Mehdi Mobli, Andreas Brust, Markus Muttenthaler, Åsa Andersson, Lotten Ragnarsson, Joel Castro, Irina Vetter, Johnny X. Huang, Mathias Nilsson, Stuart M. Brierley, Matthew A. Cooper, Richard J. Lewis and Paul F. Alewood
 
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We demonstrate efficient ‘click’ synthesis of large dendrimeric oxidatively folded peptides with up to 16 copies of [Lys8]-oxytocin that maintain potency and structure.

Published online 14 October 2016

CH16438Interpenetrated Double Pillared-Layer CoII MOFs with pcu Topology

In-Hyeok Park, Yunji Kang, Eunji Lee, Anjana Chanthapally, Shim Sung Lee and Jagadese J. Vittal
 
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The influence of organic backbone on the bonding modes of the dicarboxylates, conformations of the of the long and flexible dipyridyl ligand, and pore size in isoreticular metal–organic frameworks formed by three double pillared-layer CoII metal–organic frameworks with a pcu topology is discussed.

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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.

Published online 05 October 2016

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
 
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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.

Published online 03 October 2016

CH16425Atomic Force Microscopy Studies of the Interaction of Antimicrobial Peptides with Bacterial Cells

Anna Mularski and Frances Separovic
 
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Many antimicrobial peptides (AMPs) are membrane-active but their mode of action remains elusive. Most studies have been conducted with synthetic membrane systems but, more recently, atomic force microscopy has been utilized to reveal the effect of AMPs on bacterial cells and provide great insight into how this class of peptides lyse cells.

Published online 28 September 2016

CH16454Effect of Hydrogen Peroxide on the Extraction of Components of Cedar Powder with Tetrabutylphosphonium Hydroxide Aqueous Solution at 60°C

Sachiko Yamanaka, Koichi Yoshioka, Hisashi Miyafuji and Hiroyuki Ohno
 
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Cedar powder was treated with ionic liquids and onium hydroxide aqueous solution under very mild condition such as at 60°C. Addition of hydrogen peroxide accelerated the dissolution of lignin fragments with larger molecular weights owing to scission of the lignin network structure.

Published online 21 September 2016

CH16368Two 3D ZnII Metal–Organic Frameworks with 3- and 8-Fold Interpenetration: Syntheses, Structures, Photodegradation, and Photoluminescent Properties

Chuan-Bin Fan, Xiang-Min Meng, Yu-Hua Fan, Zi-Ao Zong, Xiao-Yin Zhang and Cai-Feng Bi
 
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Two novel zinc coordination polymers have been synthesised and characterised. Their topological structures show 4-connected 8- and 3-fold interpenetrating 3D frameworks. Furthermore, they exhibit good photodegradation capability and photoluminescence properties.

Published online 15 September 2016

CH16138Effect of Alkyl Chain Length of Imidazolium Cation on the Electroreduction of CO2 to CO on Ag Electrode in Acetonitrile

Qianqian Wang, Chengzhen Chen, Juhua Zhong, Bo Zhang and Zhenmin Cheng
 
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Effect of imidazolium cation (MIM+) on the electroreduction of CO2 to CO was investigated by linear sweep voltammetry (LSV), cyclic voltammetry (CV), constant potential electrolysis (CPE), and density functional theory (DFT) computations. It is interesting to find that the catalytic effect of MIM+ is sensitive to the alkyl chain length on its N1-position.

Published online 15 September 2016

CH16429Sweet Poisons: Synthetic Strategies towards Tutin Glycosides

Duong Nhu, Lesley Larsen, Nigel B. Perry, David S. Larsen and Bill C. Hawkins
 
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Various glycosylation reactions were tried in an effort to synthesise β-linked tutin glycosides, found in toxic honeys. Cationic palladium-mediated glycosylation gave the α-linked tutin tetrabenzyl glucoside (5 : 1, α : β). Hydrogenolysis of the benzyl ether groups resulted in tutin double-bond migration. Epoxide opening and rearrangement were observed upon acetylation of the tutin glucoside.

Published online 08 September 2016

CH16333Syntheses and Characterizations of Three Organically Templated Zinc Phosphites with 12-Ring Channels

Zhen-Zhen Bao, Song-De Han, Jin-Hua Li, Guo-Ming Wang and Zong-Hua Wang
 
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Three zinc phosphites have been synthesized and characterized. Their frameworks are constructed from 4-connected ZnO4 tetrahedra and 3-connected HPO3 pseudopyramids. There are 12-membered ring (12-MR) and 8-MR apertures in their (3,4)-connected network. Helical chains are observed in compound 3.

Published online 08 September 2016

CH16320Preparation of CoWO4/g-C3N4 and its Ultra-Deep Desulfurization Property

Pengfei Xing, Rongxiang Zhao, Xiuping Li and Xiaohan Gao
 
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CoWO4/g-C3N4 was synthesized by precipitation and calcination, and used as a catalyst for oxidative desulfurization. In the process, CoWO4/g-C3N4 showed excellent desulfurization activity and the desulfurization rate reached 92.9 %. Moreover, the catalyst could be recycled at least five times without any clear decrease in catalytic activity.

Published online 08 September 2016

CH16467Endocyclic and Endo–Exocyclic Silver(I) Complexes of Thiaoxaaza Macrocycles: Crystallographic and NMR Studies

Yunji Kang, Hyeong-Hwan Lee, Huiyeong Ju, Eunji Lee, Seulgi Kim, Joon-Hwa Lee, In-Hyeok Park and Shim Sung Lee
 
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Thiaoxaaza macrocycles incorporating NO2S2 (L1) and NO2S3 (L2) donors were employed and their silver(i) nitrate complexation in solid and solution states was investigated.

Published online 25 August 2016

CH16236Novel SrO-CaO Mixed Metal Oxides Catalyst for Ultrasonic-Assisted Transesterification of Jatropha Oil into Biodiesel

Syed Danish Ali, Isma Noreen Javed, Usman Ali Rana, Muhammad Faizan Nazar, Waqas Ahmed, Asifa Junaid, Mahmood Pasha, Rumana Nazir and Rizwana Nazir
 
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Novel strontium oxide/calcium oxide (SrO-CaO) mixed metal oxides heterogeneous catalyst is synthesized to highlight its catalytic potential for the transformation of Jatropha oil to green biofuels via an ultrasonic-assisted transesterification process.

Published online 22 August 2016

CH16180Synthesis of a Novel Dibenzylamide Derivative of p-tert-Octylcalix[4]arene and its Extraction Properties Towards Noble Metal Ions

Jee Young Kim, Yoga Priastomo, Shintaro Morisada, Hidetaka Kawakita, Keisuke Ohto and Yang Kim
 
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A N,N-dibenzylacetoamide derivative of p-tert-octylcalix[4]arene has been synthesised and its solvent extraction of precious metals in nitric acid media was investigated for determining the effects of extractant concentration and its contact time as well as nitric acid concentration in comparison with a N,N-diethylacetoamide derivative.

Published online 01 August 2016

CH16250Preparation of Magnetic Surface-Imprinted Polymer Microspheres with Hydrophilic External Layers for Selective Extraction of Fluoroquinolones from Eggs

Yun-Kai Lv, Xue Xiong, Fang-Fang Zhao, Meng-Zhe Li, Mian Wang and Xiao-Yang Li
 
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Novel restricted access media–molecularly imprinted magnetic microspheres that displayed water-compatibility, exclusion of biomacromolecules, and selective enrichment of analytes were prepared by a one-pot surface imprinting method for the magnetic dispersion microextraction of trace fluoroquinolones from egg samples.

Published online 29 July 2016

CH16239(Diacetoxyiodo)benzene: More Than an Oxidant

Rosana Helena C. N. Freitas
 
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Although PhI(OAc)2 is known as an oxidizing agent, it can also serve as a reagent or a catalyst in different types of chemical reactions in organic synthesis. PhI(OAc)2 is used in radical reactions, oxidation reactions, and in heterocycle synthesis. This paper reports some relevant and recent new uses of PhI(OAc)2.

Graphical Abstract Image

Poly(γ-4-methylbenzyl-L-glutamate) pyridinium tetrafluoroborate conjugates with constant main chain length, various pyridinium pendants, and high grafting efficiency can be readily prepared by nucleophilic substitution and ion-exchange reaction. They can exhibit reversible UCST-type phase behaviours in both methanol and water depending on the type of pyridinium pendants.

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