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 10 2017

CH17036Synthesis of Imines and Amines from Furfurals Using Continuous Flow Processing

Boris Bizet, Christian H. Hornung, Thomas M. Kohl and John Tsanaktsidis
pp. 1069-1072
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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.

CH17060Electrophoretic Deposition of SnFe2O4–Graphene Hybrid Films as Anodes for Lithium Ion Batteries

Tao Xu, Qinghan Meng, Meng Yang, Wanyuan Zhi and Bing Cao
pp. 1073-1081
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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.

CH17194Studies on Orpiment (As2S3) Quantum Dots and their Self-Assemblies

Jinzhu Wu, Yaxiu Feng, Haishu Lin and Paul C. Ho
pp. 1093-1098
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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.

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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.

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
pp. 1106-1109
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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.

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
pp. 1110-1117
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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.

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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.

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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.

CH17172Cobalt Species Active for Nitrous Oxide (N2O) Decomposition within a Temperature Range of 300–600°C

Naseer A. Khan, Eric M. Kennedy, Bogdan Z. Dlugogorski, Adesoji A. Adesina and Michael Stockenhuber
pp. 1138-1145
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Catalyst supports play a vital role in the formation of active cobalt sites for the N2O decomposition reaction. Co2+ and Co3+ are the highly active cobalt species. The acidic properties of the ZSM-5 support changes with the cobalt loading.

CH17227Efficient Synthesis of an Indinavir Precursor from Biomass-Derived (–)-Levoglucosenone

Edward T. Ledingham, Kieran P. Stockton and Ben W. Greatrex
pp. 1146-1150
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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.

Online Early

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

Published online 18 October 2017

CH17354Ultrafast NH3 Sensing Properties of WO3@CoWO4 Heterojunction Nanofibres at Room Temperature

Yiming Zhao, Muhammad Ikram, Jianzhou Wang, Zhi Liu, Lijuan Du, Jiao Zhou, Kan Kan, Weijun Zhang, Li Li and Keying Shi
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A Co-W nanofibre sensor was found to exhibit excellent gas-sensing properties at room temperature, such as a response of 1.17 and 3 s to 1000 ppm NH3, and the response time always remained within 5 s for a NH3 concentration range of 1000–10 ppm, due to the single crystal CoWO4–CoWO4 homojunctions and unique massage ball-like WO3–CoWO4 heterojunctions.

Published online 16 October 2017

CH17359First Year Introductory Chemistry at the University of Western Australia: Reflections and Perceptions

Tristan D. Clemons, Robert B. Bucat and Dino Spagnoli
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This study investigated the motivations and attitudes of two student cohorts enrolled in an introductory chemistry unit, which Emeritus Professor Graham Chandler helped to create. An interview with Graham describes the origins of this unit. Therefore, this study has particular interest in this special issue celebrating Graham’s career in chemistry.

Published online 11 October 2017

CH17334A Novel Strategy to Introduce 18F, a Positron Emitting Radionuclide, into a Gallium Nitrate Complex: Synthesis, NMR, X-Ray Crystal Structure, and Preliminary Studies on Radiolabelling with 18F

Taracad K. Venkatachalam, Paul V. Bernhardt, Damion H. R. Stimson, Gregory K. Pierens, Rajiv Bhalla and David C. Reutens
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Substituted diphenyl dithiosemicarbazone gallium nitrate and fluoride complexes have been synthesised and the structures confirmed by NMR and X-ray crystallography. Radiolabelling of the nitrate complexes has been performed with fluorine-18, resulting in the formation of Ga-18F complexes.

Published online 10 October 2017

CH17214An Injectable Oxidized Carboxymethyl Cellulose/Polyacryloyl Hydrazide Hydrogel via Schiff Base Reaction

Xueying Sheng, Xian Li, Mengting Li, Renyi Zhang, Shuang Deng, Wangkai Yang, Guanjun Chang and Xu Ye
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A series of injectable oxi-CMC/PAH hydrogels was prepared via a Schiff base reaction under physiological conditions. The oxi-CMC6/PAH3 hydrogel exhibited good comprehensive properties and in vitro sustained release of BSA, showing that it could be potentially applied in the fields of drug delivery vehicles, tissue engineering, and cell encapsulation materials.

Published online 06 October 2017

CH17456Effect of Structured Surfaces on MALDI Analyte Peak Intensities

Sajid Bashir, Jingbo L. Liu and Peter J. Derrick
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A surface modification method is presented where sodium chloride crystal was deposited onto a stainless steel surface. The surface was subjected to various stimuli to induce surface defects either on the surface or crystal and the ion yield of substance P was investigated as a function of stimuli. The interaction of the laser resulted in an increase in the ion yield of substance P (3–17 fold increase relative to no stimuli).

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N,N-Dialkyl-N′-chlorosulfonyl chloroformamidines 1 reacted regioselectively with benzimidazoles bearing an activated methylene group at C2 to afford derivatives of the new benzo[4,5]imidazo[1,2-b][1,2,6]thiadiazine ring system. Substitution reactions of the new system occurred selectively at N5 (not at N2).

Published online 21 September 2017

CH174761,3-Dipolar Cycloaddition of a Nitronyl Nitroxide-Substituted Alkyne to Heteroaromatic N-Imines

Vasiliy Romanov, Aleksey Vorob'ev, Irina Bagryanskaya, Dmitriy Parkhomenko and Evgeny Tretyakov
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We report on the 1,3-dipolar cycloaddition of the triple bond in an ethynyl-substituted nitronyl nitroxide to heteroaromatic N-imines. The reaction opens a new pathway to polyfunctional nitronyl nitroxides with pyrazolo[1,5-a]pyridine or related substituents that are in demand in coordination chemistry and molecular magnetism fields.

Published online 20 September 2017

CH17202Investigation of Hybrid Materials Based on Polyurethane Modified with Aliphatic Side Chains Combined with Nano-TiO2

Jie Zhang, Nanjie Zhang, Quan Liu, Haojun Ren, Pengfei Li and Kang Yang
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Polyurethanes (PUs) were synthesised using methylene diphenyl diisocyanate (MDI), polytetrahydrofuran ether diol (PTMG), and chain extenders containing different amounts of aliphatic side chains. Hybrid materials were then prepared by reacting the PUs with nano-TiO2. The effects of different molecular structures of the chain extenders on the surface properties of PU coatings and the hybrid materials were investigated.

Published online 15 September 2017

CH17363Laser-Based Formation of Copper Nanoparticles in Aqueous Solution: Optical Properties, Particle Size Distributions, and Formation Kinetics

Ashley J. Mulder, Rhys D. Tilbury, Phillip J. Wright, Thomas Becker, Massimiliano Massi and Mark A. Buntine
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The formation of copper nanoparticles (CuNPs) in the presence of N-donor ligands results in changes in the nanoparticle optical properties and particle size distributions, depending on the nature of the donor ligands. CuNP formation kinetics are independent of the nature of the donor ligand.

Published online 13 September 2017

CH17391Synthesis of Star Polymers by RAFT Polymerization as Versatile Nanoparticles for Biomedical Applications

Jinming Hu, Ruirui Qiao, Michael R. Whittaker, John F. Quinn and Thomas P. Davis
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Synthesis of star polymers using reversible addition–fragmentation chain transfer (RAFT) polymerization through core-first and arm-first preparation are outlined. Biomedical applications of the resulting star polymers in controlled delivery of chemotherapeutic agents, protein inhibitors, signalling molecules, siRNA, and in constructing macromolecular magnetic resonance imaging (MRI) contrast agents and fluorescent imaging agents, and theranostic vectors are discussed.

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Portable dielectric barrier discharge ionization is a plasma-based ion source for mass spectrometry that is significantly ‘softer’ than the two most widely used plasma-based ionization sources. This is important for the detection of intact molecules with thermolabile bonds, such as many explosives, and some chemical weapons and organic pollutants.

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A series of carbon-based solid acid catalysts derived from biomass was prepared and used for the conversion of fructose to 5-HMF, which is a very important platform chemical due to its unique chemical structure. The results suggest that sulfonated carbon materials exhibit remarkable catalytic capability for fructose dehydration to 5-HMF.

Published online 31 August 2017

CH17380Application of Hole-Transporting Materials as the Interlayer in Graphene Oxide/Single-Wall Carbon Nanotube Silicon Heterojunction Solar Cells

LePing Yu, Tom Grace, Hong Duc Pham, Munkhbayar Batmunkh, Mahnaz Dadkhah, Cameron Shearer, Prashant Sonar and Joe Shapter
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New hole-transport materials have been applied in silicon–carbon nanotube solar cells to yield better performance.

Published online 29 August 2017

CH17257Methanal Extrusion in ipso-Substitution Reactions of Hydroxymethylindoles

Jeremy C. Dobrowolski, Kittiya Somphol, Mardi Santoso, Hung Duong, Christopher R. Gardner, Naresh Kumar and David StC. Black
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A range of 3-hydroxymethylindoles undergo acid-catalysed reactions involving ipso-electrophilic substitution with the extrusion of methanal and the formation of diindolylmethane moieties. Both inter- and intramolecular processes lead to macrocyclic compounds.

Published online 28 August 2017

CH17228The Use of Imaging Mass Spectrometry to Study Peptide Toxin Distribution in Australian Sea Anemones

Michela L. Mitchell, Brett R. Hamilton, Bruno Madio, Rodrigo A. V. Morales, Gerry Q. Tonkin-Hill, Anthony T. Papenfuss, Anthony W. Purcell, Glenn F. King, Eivind A. B. Undheim and Raymond S. Norton
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Peptide toxins from sea anemones may provide valuable drug leads. However, little is known about peptide toxin distribution in discrete morphological regions in sea anemones, which perform distinct biological functions. We utilise imaging mass spectrometry to examine peptide distribution in the Australian sea anemone, Oulactis muscosa, and infer biological function.

Published online 21 August 2017

CH17277A Novel Cancer Nanotheranostics System Based on Quantum Dots Encapsulated by a Polymer-Prodrug with Controlled Release Behaviour

Hai-Kang Huang, Jing Yan, Pei Liu, Bi-Yun Zhao, Yi Cao and Xue-Fei Zhang
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A prodrug mPEG-b-PCL-(g-PTX)-b-PLA-(g-LA) has been synthesized, which may exchange ligands with QDs to form a nanotheranostic system (prodrug-co-QDs). This novel system exhibited good controlled drug release behaviour due to the ester linkage between the drug and polymer. By using typical cancer cell lines, we showed that this nanotheranostic system is promising in cancer diagnosis and treatment in vitro.

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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.

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 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

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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