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IN THIS ISSUE ISSN 1359–7345 CODEN CHCOFS 48(81) 10057–10148 (2012)

Cover Inside cover See M. Bele´n Serrano-Santos See Martin Pumera et al., et al., pp. 10087–10089. pp. 10090–10092. Image reproduced by permission Image reproduced by permission of Thomas Scha¨fer from of Martin Pumera from Chem. Commun., 2012, 48, 10087. Chem. Commun., 2012, 48, 10090.

PROFILE

10068 Interview with Steve Davies

Colleagues, students, zebra fish, fruit flies, worms and bankers—Steve Davies is happy to work with them all for the good of chemistry. He reveals why he is a very lucky man.

FEATURE ARTICLE

10069 Synthesis of p-extended porphyrins via intramolecular oxidative coupling

Jan P. Lewtak and Daniel T. Gryko* Fusion of porphyrins with other aromatic units at the meso- and b-positions results in very strong bathochromic shifts of absorption.

This journal is & The Royal Society of Chemistry 2012 Chem. Commun., 2012, 48, 10059–10067 | 10059 EDITORIAL STAFF ChemComm Editor Robert Eagling Chemical Communications Deputy editor Joanne Thomson www.rsc.org/chemcomm Senior publishing editor Philippa Ross EDITORIAL BOARD Development editor Ross McLaren Chair Can Li, Dalian Institute of Chemical Members Publishing editors Richard R. Schrock, Massachusetts Physics Penny Brothers, The University of Will Dennis, Rowan Frame, Celia Gitterman, Institute of Technology Jean-Louis Reymond, University of Berne Auckland Alan Holder, Marc Hutchby, Eleanor Merritt, Associate Editors Manfred Scheer, University of Keiji Maruoka, Kyoto University Tamsin Phillips, Matthew Reaveley Antonio M. Echavarren, Institute of Regensburg Heather Maynard, University of Publishing assistants Chemical Research of Catalonia Jonathan L. Sessler, University of California, Los Angeles Rachel Blakeburn, Bethany Johnson, Kate McCallum Steven De Feyter, Catholic Texas at Austin Nicholas J. Turner, University of Publisher University of Leuven Jonathan W. Steed, Durham Manchester Emma Wilson Daniel Gamelin, University of University For queries about submitted papers, please contact Washington T. Don Tilley, University of California, Philippa Ross, Senior publishing editor in the first Michael Krische, University of Texas Berkeley instance. E-mail [email protected] at Austin Yong-Qiang Tu, Lanzhou University For pre-submission queries please contact Robert Eagling, Editor. Email [email protected] ADVISORY BOARD Chemical Communications (print: ISSN 1359-7345; electronic: ISSN 1364-548X) is published 100 times a year by Varinder Aggarwal, University of Bristol Andrew B. Holmes, University of Achim Müller, University of Bielefeld the Royal Society of Chemistry, Thomas Graham House, Jerry L. 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Santa Barbara of Technology Advertisement sales: Tel +44 (0) 1223 432246; Fax +44 (0) 1223 426017; E-mail [email protected] INFORMATION FOR AUTHORS For marketing opportunities relating to this journal, contact [email protected] Full details on how to submit material for publication in Regulation 2003, this publication may only be reproduced, Chemical Communications are given in the Instructions stored or transmitted, in any form or by any means, with for Authors (available from http://www.rsc.org/authors). the prior permission in writing of the Publishers or in the Submissions should be made via the journal’s homepage: case of reprographic reproduction in accordance with http://www.rsc.org/chemcomm. the terms of licences issued by the Copyright Licensing Agency in the UK. US copyright law is applicable to users Authors may reproduce/republish portions of their in the USA. published contribution without seeking permission from the RSC, provided that any such republication is The Royal Society of Chemistry takes reasonable care in the accompanied by an acknowledgement in the form: preparation of this publication but does not accept liability (Original Citation)–Reproduced by permission of for the consequences of any errors or omissions. The Royal Society of Chemistry. {f The paper used in this publication meets the This journal is © The Royal Society of Chemistry 2012. requirements of ANSI/NISO Z39.48–1992 Apart from fair dealing for the purposes of research or (Permanence of Paper). private study for non-commercial purposes, or criticism Royal Society of Chemistry: Registered Charity No. 207890. or review, as permitted under the Copyright, Designs and Patents Act 1988 and the Copyright and Related Rights COMMUNICATIONS

10087 Characterization of structural changes in aptamer films for controlled release nanodevices

M. Bele´n Serrano-Santos,* Eduard Llobet, Veli C. O¨zalp and Thomas Scha¨fer The dimension of the conformational changes of DNA-aptamers has been determined by acoustic wave-based sensors upon recognition of adenosine-50-monophosphate (AMP).

10090 Micromotors with built-in compasses

Guanjia Zhao, Samuel Sanchez, Oliver G. Schmidt and Martin Pumera* Magnetized iron containing microjets can sense the direction of an external magnetic field and align the directionalities of their movements accordingly.

10093

Biocarbon-coated LiFePO4 nucleus nanoparticles enhancing electrochemical performances

Xueguang Zhang, Xudong Zhang,* Wen He,* Yuanzheng Yue, Hong Liu and Jingyun Ma We report a green biomimetic method to synthesize biocarbon-coated LiFePO4 nucleus nanoparticles using yeast cells as both a structural template and a biocarbon source for high-power lithium-ion batteries.

10096 Metal nanoparticle catalysts decorated with metal oxide clusters

Neema A. Mashayekhi, Yi Y. Wu, Mayfair C. Kung* and Harold H. Kung* A method was developed to synthesize metal nanoparticles decorated with mononuclear metal oxide units dispersed in clusters or patches of another oxide.

This journal is & The Royal Society of Chemistry 2012 Chem. Commun., 2012, 48, 10059–10067 | 10061 COMMUNICATIONS

10099 Synthesis, solvatochromism, aggregation-induced emission and cell imaging of tetraphenylethene-containing BODIPY derivatives with large Stokes shifts

Rongrong Hu, C. F. Azael Go´mez-Dura´n, Jacky W. Y. Lam, Jose´L. Belmonte-Va´zquez, Chunmei Deng, Sijie Chen, Ruquan Ye, Eduardo Pen˜a-Cabrera,* Yongchun Zhong, Kam Sing Wong and Ben Zhong Tang* A series of tetraphenylethene-containing BODIPYs with tunable emission colors and large Stokes shift are reported.

10102 Microfluidic size selective growth of palladium nano-particles on carbon nano-onions

Faizah Md Yasin, Ramiz A. Boulos, Boon Yong Hong, Andrew Cornejo, K. Swaminathan Iyer, Lizhen Gao, Hui Tong Chua and Colin L. Raston* Dynamic thin films of dispersed carbon nano-onions decorated with Pd2+ and p-phosphonic acid calix[8]arene allow controlled surface growth of Pd nano-particles 2–7 nm in diameter.

10105 Discrimination of nerve gases mimics and other organophosphorous derivatives in gas phase using a colorimetric probe array

Katherine Chulvi, Pablo Gavin˜a, Ana M. Costero,* Salvador Gil, Margarita Parra, Rau´l Gotor, Santiago Royo, Ramo´n Martı´nez-Ma´n˜ez,* Felix Sanceno´n and Jose´-L. Vivancos The array allows us to classify the nerve agent simulants DFP, DCP and DCNP.

10108 New highly soluble dimedone-derived iodonium ylides: preparation, X-ray structure, and reaction with carbodiimide leading to oxazole derivatives

Chenjie Zhu, Akira Yoshimura, Pavlo Solntsev, Lei Ji, Yunyang Wei, Victor N. Nemykin* and Viktor V. Zhdankin* New highly soluble dimedone-based aryliodonium ylides are useful reagents for the preparation of oxazole derivatives by reaction with carbodiimides.

10062 | Chem. Commun., 2012, 48, 10059–10067 This journal is & The Royal Society of Chemistry 2012 ChemSpider can help you! I need to know We know that chemical naming is hard and that trivial names the structure of hide complex structures. this compound We want to make it easy for you to find this information wherever you are:

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www.chemspider.com Registered Charity Number 207890 COMMUNICATIONS

10111 4,40-Bithiazole-based tetraarylenes: new photochromes with unique photoreactive patterns

Gildas Gavrel, Pei Yu,* Anne Le´austic, Re´gis Guillot, Re´mi Me´tivier and Keitaro Nakatani Tetraarylene-based photochromes offer more functionalizable sites and a new way to design biphotochromes.

10114 Fast pH-assisted functionalization of silver nanoparticles with monothiolated DNA

Xu Zhang, Mark R. Servos and Juewen Liu* While NaCl assists DNA adsorption to AuNPs at neutral pH, this is ineffective for AgNPs; low pH significantly accelerates DNA adsorption to AgNPs.

10117

nBu4NI-catalyzed direct synthesis of a-ketoamides from aryl methyl ketones with dialkylformamides in water using TBHP as oxidant

Wen-Peng Mai,* Hui-Hui Wang, Zhi-Cheng Li, Jin-Wei Yuan, Yong-Mei Xiao, Liang-Ru Yang, Pu Mao and Ling-Bo Qu* A novel and easy practical direct synthesis of a-ketoamides has been developed without metals in water. This procedure was catalyzed by nBu4NI using TBHP as oxidant from simple substrates, aryl methyl ketones and dialkylformamides.

10120 Fluorogenic detection of hydrogen sulfide via reductive unmasking of o-azidomethylbenzoyl-coumarin conjugate

Zhisheng Wu, Zhu Li, Liu Yang, Jiahuai Han and Shoufa Han* Fluorescent detection of hydrogen sulfide was achieved with 7-o-20-(azidomethyl)benzoyl-4-methylcoumarin via analyte mediated reductive removal of the 20-(azidomethyl)benzoyl moiety and release of 7-hydroxy-4-methylcoumarin.

10064 | Chem. Commun., 2012, 48, 10059–10067 This journal is & The Royal Society of Chemistry 2012 COMMUNICATIONS

10123 A label-free real time fluorometric assay for protease and inhibitor screening with a released heme

Wenying Li, Jian Chen, Huping Jiao, Qingfeng Zhang, Huipeng Zhou and Cong Yu* A label free continuous assay for protease activity and inhibitor screening based on a released heme has been developed.

10126 Light-regulated host–guest interaction as a new strategy for intracellular PEG-detachable polyplexes to facilitate nuclear entry

Wenyu Li, Youxiang Wang,* Lina Chen, Zhixiong Huang, Qiaoling Hu and Jian Ji The intracellular light-regulated dePEGylation is exploited firstly to facilitate DNA release and nuclear entry, thus resulting in efficient transfection.

10129 On the aromatic stabilization of benzenoid hydrocarbons

Arkadiusz Ciesielski,* Dorota K. Stepien´, Michaz A. Dobrowolski, yukasz Dobrzycki and Michaz K. Cyran´ski* We present a general scheme for estimation of aromatic stabilization energies of benzenoid hydrocarbons based on selected topological features.

10132 Lewis acid-catalyzed Friedel–Crafts alkylations of 3-hydroxy-2-oxindole: an efficient approach to the core structure of azonazine

Santanu Ghosh, Lakshmana K. Kinthada, Subhajit Bhunia and Alakesh Bisai* A Lewis acid catalyzed Friedel–Crafts reaction of phenol derivatives with 3-alkyl-3-hydroxy-2-oxindole (5) has been investigated. The methodology provides a straightforward access to the tetracyclic core of azonazine (2).

This journal is & The Royal Society of Chemistry 2012 Chem. Commun., 2012, 48, 10059–10067 | 10065 COMMUNICATIONS

10135 First tellurium-containing phthalocyanine analogues: strong effect of tellurium on spectral, redox and conductivity properties of porphyrazines with annulated chalcogenodiazole ring(s)

P. A. Stuzhin,* M. S. Mikhailov, E. S. Yurina, M. I. Bazanov, O. I. Koifman, G. L. Pakhomov, V. V. Travkin and A. A. Sinelshchikova The introduction of tellurium in 1,2,5-chalcogenodiazolo- porphyrazines stabilises the LUMO, facilitates the reduction of the macrocycle and strongly increases the conductivity of fabricated thin films.

10138 The first asymmetric ring-expansion carbonylation of meso-epoxides

Prasad Ganji and Hasim Ibrahim*

Chiral Cr(III) chloro complexes catalyse the ring-expansion carbonylation of meso-epoxides with significant levels of asymmetric induction.

10141 A versatile fluorescence approach to kinetic studies of hydrocarbon autoxidations and their inhibition by radical-trapping antioxidants

Jason J. Hanthorn, Evan Haidasz, Paul Gebhardt and Derek A. Pratt* We report a simple coumarin–triarylphosphine conjugate that undergoes fluorescence enhancement upon reaction with hydroperoxides and demonstrate its use to follow autoxidations of 7-dehydrocholesterol (at 37 1C) and hexadecane (at 160 1C) and their inhibition by antioxidants.

10144 Room-temperature synthesis of soluble, fluorescent carbon nanoparticles from organogel precursors

Jules Rome´oNe´abo, Ce´cile Vigier-Carrie` re, Simon Rondeau-Gagne´and Jean-Franc¸ois Morin* Carbon nanoparticles were obtained at room temperature by irradiating an organogel made from a 1,8-diaryloctatetrayne derivative in chloroform. During the topochemical polymerization, the morphology of the gel changes from fibers to soluble, yellow fluorescent nanoparticles in high yield. Analyses suggest that the resulting nanoparticles are made of amorphous graphitic carbon.

10066 | Chem. Commun., 2012, 48, 10059–10067 This journal is & The Royal Society of Chemistry 2012 The best recruitment site dedicated to chemistry and the chemical sciences

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