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

Australian Journal of Chemistry

Volume 68 Number 9 2015

RESEARCH FRONT: 2014 RACI National Congress

CH15406Total Radiosynthesis: Thinking Outside ‘the Box'

Steven H. Liang and Neil Vasdev
pp. 1319-1328
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A new avenue to develop radiotracers that were previously unattainable owing to the lack of efficient radiosynthetic methods is necessary to work towards our ultimate, albeit impossible goal – the concept we term total radiosynthesis – to radiolabel virtually any molecule.

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The structures of a series of heterocyclic α-oxo-oximes were investigated experimentally and computationally. The preferred configurations of α-oxo-oximes can be understood on the basis of steric hindrance (disfavouring E isomers), lone-pair repulsion between C=O and OH groups (disfavouring ZE isomers), and, most importantly, intramolecular H-bonding (favouring ZZ isomers) and intermolecular H-bonding (favouring EE isomers).

CH15134Adsorption of Water and Methanol on Highly Graphitized Thermal Carbon Black and Activated Carbon Fibre

Toshihide Horikawa, Masanori Takenouchi, Duong D. Do, Ken-Ichiro Sotowa, J. Rafael Alcántara-Avila and David Nicholson
pp. 1336-1341
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The effects of changing the concentration of the functional groups on water adsorption on activated carbon fibres which were treated by oxidation or reduction were investigated. The onset of water adsorption in the micropores shifts to lower pressure when the concentration of functional groups is high, and vice versa.

CH15178Syntheses of Iron(0) Complexes of Symmetrical Trialkylphosphines with Three Terminal Vinyl Groups, P((CH2)mCH=CH2)3

Georgette M. Lang, Dirk Skaper, Takanori Shima, Michael Otto, Leyong Wang and John A. Gladysz
pp. 1342-1351
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(BDA)Fe(CO)3 (BDA = benzylideneacetone) is sequentially treated with P((CH2)mCH=CH2)3 (m = 4–8), NO+BF4, and n-Bu4N+X (X = Cl, Br, I, CN) to give three series of trigonal bipyramidal trans bis(phosphine) complexes, 2 (60–75 %), 3 (88–98 %), and 4-X (73–93 %), all of which can potentially undergo three-fold intramolecular ring-closing metatheses to give gyroscope-like complexes VII.

CH15136Fe(dppe)(η5-C5Me5)-Based Phenylalkynyl Complexes Featuring an NO2 End Group: A Theoretical Analysis

Hiba Sahnoune, Nicolas Gauthier, Katy Green, Karine Costuas, Frédéric Paul and Jean-François Halet
pp. 1352-1358
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Electronic structures and optical properties of a series of compounds Fe(dppe)(η5-C5Me5){[C≡C(1,4-C6H4)]nNO2} (13; n = 1–3) were investigated using density functional theory and time-dependent density functional theory computations. The extension of the carbon-rich chain has a moderate influence on the electronic properties of the compounds in their ground state, but affects notably their spectroscopic properties, with some unexpected hypsochromic shift of the lower energy absorption bands upon carbon chain lengthening.

CH15196Enhanced Squaraine Rotaxane Endoperoxide Chemiluminescence in Acidic Alcohols

Evan M. Peck, Allen G. Oliver and Bradley D. Smith
pp. 1359-1364
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The chemiluminescence of squaraine rotaxane endoperoxide is greatly enhanced in acidic alcohol solvents. The interlocked rotaxane structure is necessary for the increased chemiluminescence, which is most likely due to an O–O cleavage process that produces a squaraine excited state.

CH15146Propargyloxyproline Regio- and Stereoisomers for Click-Conjugation of Peptides: Synthesis and Application in Linear and Cyclic Peptides

Susan E. Northfield, Simon J. Mountford, Jerome Wielens, Mengjie Liu, Lei Zhang, Herbert Herzog, Nicholas D. Holliday, Martin J. Scanlon, Michael W. Parker, David K. Chalmers and Philip E. Thompson
pp. 1365-1372
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A range of isomers of Fmoc-propargyloxyproline have been prepared to give access to proline-linked peptide conjugates. Such conjugates can retain the binding affinity and/or binding conformation of the parent peptide as shown with studies of ligands for the Y1 receptor and HIV integrase.

CH15169C-Terminal Modifications Broaden Activity of the Proline-Rich Antimicrobial Peptide, Chex1-Arg20

Wenyi Li, Julien Tailhades, M. Akhter Hossain, Neil M. O'Brien-Simpson, Eric C. Reynolds, Laszlo Otvos, Frances Separovic and John D. Wade
pp. 1373-1378
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C-Terminal modifications extended the antibacterial activity of a proline-rich peptide to other Gram-negative species. Such modifications may aid in the development of more potent proline-rich antimicrobial peptides with a greater spectrum of activity against Gram-negative bacteria than the parent peptide.

CH15218RhI-Catalyzed Stille-Type Coupling of Diazoesters with Aryl Trimethylstannanes

Zhen Liu, Ying Xia, Sheng Feng, Shuai Wang, Di Qiu, Yan Zhang and Jianbo Wang
pp. 1379-1384
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A RhI-catalyzed cross-coupling of diazoester with arylstannane was developed, which represents the first Stille-type coupling that uses a diazo compound as the coupling partner. The reaction provides an alternative approach for the synthesis of α-aryl esters. RhI–carbene migratory insertion process is suggested to be involved as the key step in this Stille-type coupling.

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Fragmentation of the complexes [RCO2Ag2(CH3CN)n]+ (n = 1 and 2) is dictated by the R group. Decarboxylation is preferred over loss of a coordinated acetonitrile for R = CH3C≡C, but ligand loss is the sole pathway when R = CH3.

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A one-dimensional Eu3+ coordination polymer bearing α-CN substituted β-diketonate and 1,10-phenanthroline ligands was prepared and revealed red emission in the solid state. Analysis of the polymer after re-dissolution and ultrafast transient absorption for model compounds provides some insight into the sensitisation efficiency from the β-diketonate to Eu3+.

CH15139Assembly of New Merocyanine Chromophores with a 1,8-Naphthalimide Core by a New Method for the Synthesis of the Methine Function

Aleksey A. Vasilev, Stanislav Baluschev, Diana Cheshmedzhieva, Sonia Ilieva, Obis D. Castaño, Juan J. Vaquero, Silvia E. Angelova and Katharina Landfester
pp. 1399-1408
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A 2-in-1 chromophore: to piece together two chromophores into one yields a more efficient chromophore system with distinct physical and chemical characteristics. A new technique based on the application of the nitro function as a leaving group in a SN-Ar reaction is developed to circumvent the limitations of using a chlorine or bromine function in the synthesis of monomethine cyanine dyes.

CH153273D-Printable Biodegradable Polyester Tissue Scaffolds for Cell Adhesion

Justin M. Sirrine, Allison M. Pekkanen, Ashley M. Nelson, Nicholas A. Chartrain, Christopher B. Williams and Timothy E. Long
pp. 1409-1414
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Synthesis and characterization of a biocompatible, biodegradable, and 3D-printable polyester (poly(tri(ethylene glycol) adipate) dimethacrylate) are demonstrated for suitability in vascularized soft-tissue scaffolding applications.

CH14708Synthesis, Absorption, and Fluorescence Studies of Coumaryl-Labelled Amino Acids and Dipeptides Linked Via Triazole Ring

Santosh Kumari, Sunita Joshi, S. M. Abdul Shakoor, Devesh S. Agarwal, Siva S. Panda, Debi D. Pant and Rajeev Sakhuja
pp. 1415-1426
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Fluorophores based on 4-triazolyl, 7-hydroxy-4-triazolylmethyl, 4-O-triazolylmethyl and 7-O-triazolylmethyl coumaryl tagged amino acids and dipeptides were synthesized by copper-catalyzed [3 + 2] cycloaddition reaction between azido or alkynyl functionalized coumarins with alkynyl or azido functionalized amino acid and dipeptides, in good to excellent yields. Steady-state absorption and fluorescence properties of the synthesized conjugates were studied.

CH14680Triethylenetetramine-Modified P123-Occluded Zr-SBA-15 Molecular Sieve for CO2 Adsorption

Fan-Ming Yang, Ying Liu, Lang Chen, Chak-Tong Au and Shuang-Feng Yin
pp. 1427-1433
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A stable and renewable adsorbent for CO2 adsorption has been developed for the first time by loading triethylenetetramine (TETA) on poly(ethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) (P123)-occluded Zr-SBA-15. The adsorbent exhibits adsorption capacity of 4.27 mmol g–1 at 50°C in a stream of 5 % CO2.

CH14715Saturated N,X-Heterocyclic Carbenes (X=N, O, S, P, Si, C, and B): Stability, Nucleophilicity, and Basicity

Zahra Azizi, Mehdi Ghambarian, Mohammad A. Rezaei and Mohammad Ghashghaee
pp. 1438-1445
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Several substitutions at the α-position of imidazolidin-2-ylidene alter the nucleophilicity, basicity, and stability of this N-heterocyclic carbene. Achieving new carbenes with a higher basicity is an important goal from both fundamental and practical points of view.

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Controlled liquid oxidization of industrial carbon black specimens was reported for the first time as an efficient synthesis and general fluorescence tuning approach to uniform-sized carbon dots with unprecedented dually tuneable emissions. Along with the customizable pH-responsive behaviours, these carbonaceous nanolights offered a promising platform for both sensing and displaying applications.

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N,N-Dialkyl-N′-chlorosulfonyl chloroformamidines 1 regioselectively reacted with 1-substituted 5-aminopyrazoles 2 to afford pyrazolo[3,4-e][1,2,4]thiadiazine dioxides 3. Methylation of 3 occurred at N2, N4, and N6. Benzylation occurred preferentially at N2. Alkylation at N6 with ethyl bromoacetate resulted in pyrazole ring expansion affording pyrimido[4,5-e][1,2,4]thiadiazines. Compounds 3 were unreactive towards acylating agents.

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Professor Kenneth Seddon OBE, one of AJC’s longest-standing Editors, sadly passed away on 21 January from prostate cancer. Ken was one of the world's best ionic liquids experts. His consistent unwavering support, loyalty and advocacy for AJC over the last 10 years will be sorely missed.