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VIEWPOINT 6827 Calixarenes and cations: a time-lapse photography of the big-bang Alessandro Casnati* Starting in the 1980s in ChemComm, the reports on cation complexation by calixarenes triggered a massive ‘‘big-bang’’ explosion of studies on these macrocycles. COMMUNICATIONS 6831 ATRP synthesis of poly(2-(methacryloyloxy)ethyl choline phosphate): a multivalent universal biomembrane adhesive Xifei Yu, Xiaoqiang Yang, Sonja Horte, Jayachandran N. Kizhakkedathu and Donald E. Brooks* Synthesis is described of a universal biomembrane adhesive based on biocompatible polymeric choline phosphate binding to any mammalian cell membrane. IN THIS ISSUE ISSN 1359–7345 CODEN CHCOFS 49(61) 6815–6922 (2013) Cover See Donald E. Brooks et al., pp. 6831–6833. Image reproduced by permission of Donald E. Brooks from Chem. Commun., 2013, 49, 6831. Inside cover See Ulrich Siemeling et al., pp. 6834–6836. Image reproduced by permission of Ulrich Siemeling from Chem. Commun., 2013, 49, 6834. ChemComm Chemical Communications www.rsc.org/chemcomm RSC Publishing is a not-for-profit publisher and a division of the Royal Society of Chemistry. Any surplus made is used to support charitable activities aimed at advancing the chemical sciences. Full details are available from www.rsc.org This journal is c The Royal Society of Chemistry 2013 Chem. Commun., 2013, 49, 6817–6826 | 6817 Published on 04 July 2013. Downloaded on 29/10/2014 17:20:21. View Article Online View Journal | View Issue

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Page 1: Contents list

VIEWPOINT

6827

Calixarenes and cations: a time-lapse photographyof the big-bang

Alessandro Casnati*

Starting in the 1980s in ChemComm, the reports oncation complexation by calixarenes triggered a massive‘‘big-bang’’ explosion of studies on these macrocycles.

COMMUNICATIONS

6831

ATRP synthesis of poly(2-(methacryloyloxy)ethylcholine phosphate): a multivalent universalbiomembrane adhesive

Xifei Yu, Xiaoqiang Yang, Sonja Horte,Jayachandran N. Kizhakkedathu and Donald E. Brooks*

Synthesis is described of a universal biomembrane adhesivebased on biocompatible polymeric choline phosphatebinding to any mammalian cell membrane.

IN THIS ISSUE

ISSN 1359–7345 CODEN CHCOFS 49(61) 6815–6922 (2013)

CoverSee Donald E. Brooks et al.,pp. 6831–6833.Image reproduced by permissionof Donald E. Brooks fromChem. Commun., 2013, 49, 6831.

Inside coverSee Ulrich Siemeling et al.,pp. 6834–6836.Image reproduced by permissionof Ulrich Siemeling fromChem. Commun., 2013, 49, 6834.

ChemCommChemical Communications

www.rsc.org/chemcomm

RSC Publishing is a not-for-profit publisher and a division of the Royal Society of Chemistry. Any surplus made is used to support charitable activitiesaimed at advancing the chemical sciences. Full details are available from www.rsc.org

This journal is �c The Royal Society of Chemistry 2013 Chem. Commun., 2013, 49, 6817–6826 | 6817

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Page 2: Contents list

EDITORIAL STAFFEditorRobert Eagling

Deputy editorJane Hordern

Senior publishing editorPhilippa Ross

Development editorJeanne Andres

Publishing editorsTamsin Cowley, Will Dennis, Celia Gitterman,Alan Holder, Eleanor Merritt, Andria Nicodemou,Matthew Reaveley

Publishing assistantsJenny Abbott, Natalie Ford, Bethany Johnson

PublisherEmma Wilson

For queries about submitted papers, please contact Philippa Ross, Senior publishing editor in the first instance. E-mail [email protected]

For pre-submission queries please contact Robert Eagling, Editor. Email [email protected]

Chemical Communications (print: ISSN 1359-7345; electronic: ISSN 1364-548X) is published 100 times a year by the Royal Society of Chemistry, Thomas Graham House, Science Park, Milton Road, Cambridge, UK CB4 0WF. All orders, with cheques made payable to the Royal Society of Chemistry, should be sent to RSC Order Department, Royal Society of Chemistry, Thomas Graham House, Science Park, Milton Road, Cambridge, CB4 0WF, UKTel +44 (0)1223 432398; E-mail [email protected]

2013 Annual (print+electronic) subscription price: £3189; US$5952. 2013 Annual (electronic) subscription price: £3030; US$5654. Customers in Canada will be subject to a surcharge to cover GST. Customers in the EU subscribing to the electronic version only will be charged VAT. If you take an institutional subscription to any RSC journal you are entitled to free, site-wide web access to that journal. You can arrange access via Internet Protocol (IP) address at www.rsc.org/ip. Customers should make payments by cheque in sterling payable on a UK clearing bank or in US dollars payable on a US clearing bank.

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For marketing opportunities relating to this journal, contact [email protected]

ChemCommChemical Communications

www.rsc.org/chemcomm

EDITORIAL BOARD

ChairRichard R. Schrock, Massachusetts

Institute of Technology

Associate EditorsPenny Brothers, The University of

Auckland

Antonio M. Echavarren, Institute of

Chemical Research of Catalonia

Steven De Feyter, Catholic University

of Leuven

Daniel Gamelin, University of

Washington

Michael Krische, University of Texas

at Austin

Can Li, Dalian Institute of Chemical

Physics

S. Ramakrishnan, Indian Institute of

Science

Jean-Louis Reymond, University of

Berne

Manfred Scheer, University of

Regensburg

Jonathan L. Sessler, University of

Texas at Austin

Jonathan W. Steed, Durham

University

T. Don Tilley, University of California,

Berkeley

Yong-Qiang Tu, Lanzhou University

ADVISORY BOARD

Polly Arnold, University of Edinburgh

Jerry L. Atwood, University of Missouri

Zhenan Bao, Stanford University

Louise Berben, University of California,

Davis

Wesley Browne, University of Groningen

Luiz Henrique Catalani, University of São

Paulo

Chi-Ming Che, University of Hong Kong

Xiao-Ming Chen, Sun Yat-Sen University

Derrick Clive, University of Alberta

Seth Cohen, University of California, San

Diego

Marcetta Darensbourg, Texas A&M

University

Shaojun Dong, Chinese Academy of

Sciences

Jairton Dupont, Institute of Chemistry,

UFRGS

Josh Figueroa, University of California,

San Diego

Alois Fürstner, Max Planck Institute for

Coal Research

Lutz Gade, University of Heidelberg

Philip Gale, University of Southampton

Nathan Gianneschi, University of

California, San Diego

David Gonzalez-Rodriguez, Autonomous

University of Madrid

Rebecca Goss, University of St Andrews

Mike Greaney, University of Manchester

Michaele Hardie, University of Leeds

Craig Hawker, University of California,

Santa Barbara

Steven M. Howdle, University of

Nottingham

Xile Hu, Federal Polytechnic of Lausanne

Feihe Huang, Zhejiang University

Susumu Kitagawa, Kyoto University

Shu Kobayashi, University of Tokyo

Eric Kool, Stanford University

Teck-Peng Loh, Nanyang

Technological University

Tien-Yau Luh, National Taiwan University

Doug MacFarlane, Monash University

Hiromitsu Maeda, Ritsumeikan University

Anna Mapp, University of Michigan

Ilan Marek, Technion, Israel Institute of

Technology

Nazario Martin, Complutense University

of Madrid

Keiji Maruoka, Kyoto University

E. W. ‘Bert’ Meijer, Eindhoven University of

Technology

Catherine Murphy, University of Illinois

Wonwoo Nam, Ewha Womans University

Cristina Nevado, University of Zürich

Jean-Francois Nierengarten, University of

Strasbourg

Dan Nocera, Massachusetts Institute of

Technology

Rachel O’Reilly, University of Warwick

Atsuhiro Osuka, Kyoto University

Sebastian Perrier, University of Sydney

Erwin Reisner, University of Cambridge

Robin Rogers, University of Alabama

Paolo Samori, University of Strasbourg

Oren A. Sherman, University of Cambridge

David Smith, University of York

Doug Stephan, University of Toronto

Zhong-Qun Tian, Xiamen University

Christine Thomas, Brandeis University

Tomas Torres, Autonomous University of

Madrid

Wilfred A. van der Donk, University of

Illinois

Sandeep Verma, Indian Institute of

Technology

Li-Jun Wan, Chinese Academy of Sciences

Helma Wennemers, ETH Zurich

Eiji Yashima, Nagoya University

Shuli You, Shanghai Institute of Organic

Chemistry

Xi Zhang, Tsinghua University

INFORMATION FOR AUTHORSFull details on how to submit material for publication in Chemical Communications are given in the Instructions for Authors (available from http://www.rsc.org/authors). Submissions should be made via the journal’s homepage: http://www.rsc.org/chemcomm.

Authors may reproduce/republish portions of their published contribution without seeking permission from the RSC, provided that any such republication is accompanied by an acknowledgement in the form: (Original Citation)–Reproduced by permission of The Royal Society of Chemistry.

This journal is © The Royal Society of Chemistry 2013. Apart from fair dealing for the purposes of research or private study for non-commercial purposes, or criticism or review, as permitted under the Copyright, Designs and Patents Act 1988 and the Copyright and Related Rights

Regulation 2003, this publication may only be reproduced, stored or transmitted, in any form or by any means, with the prior permission in writing of the Publishers or in the case of reprographic reproduction in accordance with the terms of licences issued by the Copyright Licensing Agency in the UK. US copyright law is applicable to users in the USA.

The Royal Society of Chemistry takes reasonable care in the preparation of this publication but does not accept liability for the consequences of any errors or omissions.

The paper used in this publication meets the requirements of ANSI/NISO Z39.48–1992 (Permanence of Paper).

Royal Society of Chemistry: Registered Charity No. 207890.

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COMMUNICATIONS

6834

Carbonylation of the simplest persistentdiaminocarbene

Tim Schulz, Christian Farber, Michael Leibold,Clemens Bruhn, Wolfgang Baumann, Detlef Selent,Timo Porsch, Max C. Holthausen and Ulrich Siemeling*

Three’s company: the prototypical carbene (Me2N)2Creacts with CO in a 2 : 1 stoichiometric ratio, affordingan unprecedented betainic oxyallyl species. This reactivitypattern is representative of acyclic diaminocarbenes whichundergo carbonylation.

6837

Palladium-catalyzed ortho-acylation of 2-arylpyridine derivatives using arylmethyl aminesas new acyl sources

Qian Zhang, Fan Yang* and Yangjie Wu*

A facile and efficient protocol for ortho-acylation of2-aryl pyridines using arylmethyl amines as newacylation reagents was developed.

6840

The mechanism of inhibition by H2 of H2-evolutionby hydrogenases

Vincent Fourmond, Carole Baffert, Kateryna Sybirna,Sebastien Dementin, Abbas Abou-Hamdan,Isabelle Meynial-Salles, Philippe Soucaille, Herve Bottinand Christophe Leger*

We demonstrate that whether or not hydrogen evolutionby FeFe or NiFe hydrogenase is significantly inhibited by H2is not a consequence of active site chemistry, but ratherrelates to H2 transport within the enzyme.

6843

A PdAg bimetallic nanocatalyst for selectivereductive amination of nitroarenes

Linsen Li, Zhiqiang Niu, Shuangfei Cai, Yun Zhi, Hao Li,Hongpan Rong, Lichen Liu, Lei Liu, Wei He* andYadong Li*

The composition-dependent selectivity of bimetallicPd1� xAgx (x = 0–1) nanocatalysts in tandem reductiveamination between nitroarenes and aldehydes led tothe discovery of the optimal Pd1Ag1.7 catalyst.

This journal is �c The Royal Society of Chemistry 2013 Chem. Commun., 2013, 49, 6817–6826 | 6819

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COMMUNICATIONS

6846

Superhydrophobic perfluorinated metal–organicframeworks

Teng-Hao Chen, Ilya Popov,* Oussama Zenasni,Olafs Daugulis and Ognjen S. Miljanic*

Three perfluorinated Cu-based metal–organic frameworks(MOFs) were prepared starting from extensively fluorinatedbiphenyl-based ligands accessed via C–H functionalization.These new materials are highly hydrophobic with watercontact angles of up to 151 7 11, they are among themost water-repellent MOFs ever reported.

6849

Rapid dissolution of DNA in a novel bio-based ionicliquid with long-term structural and chemicalstability: successful recycling of the ionic liquid forreuse in the process

Chandrakant Mukesh, Dibyendu Mondal,Mukesh Sharma and Kamalesh Prasad*

DNA (from salmon testes) was solubilised in choline-indole-3-acetate (both pristine and recycled) in 6 h with long termchemical and structural stability.

6852

A facile and high-recovery material for rare-metalsbased on a water-soluble polyallylamine withside-chain thiourea groups

Daisuke Nagai,* Megumi Yoshida, Takuya Kishi,Hisatoyo Morinaga, Yusuke Hara, Masanobu Mori,Satoshi Kawakami and Kenji Inoue

We developed a facile and high-recovery material for raremetals based on a water-soluble polymer bearing thioureagroups.

6855

A straightforward approach to oxide-free coppernanoparticles by thermal decomposition of acopper(I) precursor

David Adner, Marcus Korb, Steffen Schulze,Michael Hietschold and Heinrich Lang*

The synthesis and application of[Cu(PPh3)2(O2CCH2OC2H4OC2H4OCH3)] for coppernanoparticle formation are reported.

6820 | Chem. Commun., 2013, 49, 6817–6826 This journal is �c The Royal Society of Chemistry 2013

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COMMUNICATIONS

6858

Spatially controlled DNA unzipping by microfluidicinterface positioning on a molecule perpendicularto a multicomponent flow

Naresh K. Mani, Sergii Rudiuk and Damien Baigl*

Intramolecular control of DNA unzipping is achieved byrotating a single DNA molecule against a longitudinalmulticomponent microfluidic flow.

6861

Dynamic control of dendrimer–fullerene associationby axial coordination to the core

Ken Albrecht, Yuto Kasai, Yasunori Kuramoto andKimihisa Yamamoto*

Fullerene association of the carbazole–phenylazomethinedendrimer was controlled by bulky pyridine complexationto the core porphyrin in an allosteric manner.

6864

Phosphorescence doping in a flexibleultramicroporous framework for high andtunable oxygen sensing efficiency

Xiao-Lin Qi, Si-Yang Liu, Rui-Biao Lin, Pei-Qin Liao,Jia-Wen Ye, Zhihui Lai, Yanyan Guan, Xiao-Ning Cheng,Jie-Peng Zhang* and Xiao-Ming Chen

Doping RuII in a flexible, fluorescent, porous coordinationpolymer gave highly oxygen sensitive materials withtunable phosphorescence quenching efficiency.

6867

Selective cleavage of 3,5-bis-(trifluoromethyl)-benzylcarbamate by SmI2–Et3N–H2O

Tobias Ankner, Anna Said Stålsmeden andGoran Hilmersson*

3,5-Bis-(trifluoromethyl)benzylcarbamate is a protectinggroup for amines with orthogonal reactivity compared tothat of the common CBz-group. Selective deprotectionwith SmI2–R3N–H2O can be conducted in the presenceof various protecting groups including the CBz-, t-Boc orTBDM groups.

This journal is �c The Royal Society of Chemistry 2013 Chem. Commun., 2013, 49, 6817–6826 | 6821

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COMMUNICATIONS

6870

Colorimetric visualization of acid–base equilibria innon-polar solvent

Atsuomi Shundo, Shinsuke Ishihara, Jan Labuta,Yosuke Onuma, Hideki Sakai, Masahiko Abe,Katsuhiko Ariga* and Jonathan P. Hill*

The multichromophoric indicator ‘porphochromone’ hasbeen used to detect acid–base equilibria in a non-polarmedium.

6873

Remarkable CO2/CH4 selectivity and CO2 adsorptioncapacity exhibited by polyamine-decoratedmetal–organic framework adsorbents

Qiuju Yan, Yichao Lin, Chunlong Kong* andLiang Chen*

Solid porous dual amine-decorated metal–organicframework adsorbents with tunable porosity have beenprepared, which exhibit remarkable CO2/CH4 selectivityand CO2 adsorption capacity.

6876

Synthesis of heterogeneous enzyme–metalnanoparticle biohybrids in aqueous media andtheir applications in C–C bond formation andtandem catalysis

Marco Filice,* Marzia Marciello,Maria del Puerto Morales and Jose M. Palomo*

Noble metals nanoparticles embedded into an enzymaticnetwork are successfully synthesized in aqueous media.These heterogeneous nanobiohybrids catalyze differentchemical reactions in excellent yields and selectivities.

6879

In situ switching layer-by-layer assembly: one-potrapid layer assembly via alternation of reductiveand oxidative electropolymerization

Mao Li,* Jian Zhang, Hai-Jing Nie, Meiyong Liao,Liwen Sang, Wenqiang Qiao, Zhi Yuan Wang,Yuguang Ma, Yu-Wu Zhong* and Katsuhiko Ariga*

In situ one-pot rapid layer-by-layer assembly ofpolymeric films as an active layer of a photoactivedevice via alternation of reductive and oxidativeelectropolymerization has been demonstrated.

6822 | Chem. Commun., 2013, 49, 6817–6826 This journal is �c The Royal Society of Chemistry 2013

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COMMUNICATIONS

6882

Novel expanded porphyrin sensitized solar cellsusing boryl oxasmaragdyrin as the sensitizer

Sandeep B. Mane, Jyun-Yu Hu, Yu-Cheng Chang,Liyang Luo,* Eric Wei-Guang Diau* andChen-Hsiung Hung*

DSSCs containing expanded core-modified porphyrins assensitizers are prepared to achieve promising energyconversion efficiency up to 5.7%.

6885

Facile synthesis of a Cu-based MOF confined inmacroporous carbon hybrid material withenhanced electrocatalytic ability

Yufan Zhang, Xiangjie Bo, Charles Luhana, Huan Wang,Mian Li and Liping Guo*

Preparation of a novel Cu-based MOF confined inmacroporous carbon composites for enhancedelectrocatalytic ability for H2O2 reduction andNADH oxidation.

6888

N-terminal a-amino group modification of peptidesby an oxime formation–exchange reactionsequence

Karen Ka-Yan Kung, Kong-Fan Wong, King-Chi Leungand Man-Kin Wong*

A site-specific and efficient method for N-terminalmodification of peptides using oxone for selectiveoxidation of N-terminal a-amino groups of peptides tooximes followed by transoximation with O-substitutedhydroxylamines has been developed.

6891

Assembly of naphthalenediimide conjugatedpeptides: aggregation induced changes influorescence

Shibaji Basak, Jayanta Nanda and Arindam Banerjee*

The synthesis, gelation and remarkable fluorescenceproperty of naphthalenediimide containing peptides havebeen presented. Gelator molecules exhibit remarkablechange and enhancement in fluorescence from sol togel transformation in mixed solvent systems.

This journal is �c The Royal Society of Chemistry 2013 Chem. Commun., 2013, 49, 6817–6826 | 6823

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COMMUNICATIONS

6894

One-dimensional self-assembly of a water solubleperylene diimide molecule by pH triggeredhydrogelation

Aniket Datar, Kaushik Balakrishnan and Ling Zang*

A water soluble perylene diimide molecule, PA-PTCDI,has been fabricated into nanofibers via a pH triggeredhydrogelation route, and the anisotropic electronic andoptical properties observed for the nanofibers areconsistent with the one-dimensional intermolecularp–p arrangement.

6897

A microporous metal–organic open frameworkcontaining uncoordinated carbonyl groups aspostsynthetic modification sites for cationexchange and Tb3+ sensing

Jianwei Cao, Yanfei Gao, Yanqin Wang, Chunfang Duand Zhiliang Liu*

A 3D microporous compound containing postsyntheticmodification sites for cation exchange was prepared.This compound can effectively and selectively serve as anantenna for sensitizing the visible-emitting Tb3+ cation.

6900

Direct 2-acetoxylation of quinoline N-oxides viacopper catalyzed C–H bond activation

Xuan Chen, Chongwei Zhu, Xiuling Cui* andYangjie Wu*

Dual C–H bond activation as a key step to construct2-acyloxyl quinolines under mild and operationallysimple conditions.

6903

Mobility on the reconstructed Pt(100)-hex surfacein ethylene and in its mixture with hydrogen andcarbon monoxide

Derek R. Butcher, Zhongwei Zhu, Baohua Mao,Hailiang Wang, Zhi Liu, Miquel Salmeron* andGabor A. Somorjai*

The mobility on the Pt(100)-hex surface was studied usinghigh-pressure STM in ethylene and in gas mixtures ofethylene, hydrogen, and CO.

6824 | Chem. Commun., 2013, 49, 6817–6826 This journal is �c The Royal Society of Chemistry 2013

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COMMUNICATIONS

6906

Hybridization chain reaction-based branchedrolling circle amplification for chemiluminescencedetection of DNA methylation

Sai Bi, Tingting Zhao, Baoyu Luo and Jun-Jie Zhu*

A novel hybridization chain reaction-based branchedrolling circle amplification combining the fabrication ofmulti-HRP-capped MNPs is developed for chemiluminescencedetection of DNA methyltransferase activities and inhibitorswith high sensitivity in a well-controlled manner.

6909

A peptide based two component white lightemitting system

Dibakar Kumar Maiti and Arindam Banerjee*

An equimolar mixture of the blue emitting donor peptideand the orange emitting acceptor peptide gives rise to anew white-light emitting substance in solution. Forsterresonance energy transfer occurs from the stilbene moietycontaining donor peptide to the PDI moiety containingacceptor peptide.

6912

Catalytic oxidative cleavage of catechol by anon-heme iron(III) complex as a green routeto dimethyl adipate

Robin Jastrzebski, Bert M. Weckhuysen andPieter C. A. Bruijnincx*

Iron(III) salts, tris(2-pyridylmethyl)amine and a base readilycatalyse the intradiol dioxygenation of pyrocatechol inmethanol, to primarily afford esters of muconic acid,which can be easily converted to dimethyl adipate.

6915

Time-resolved fluorescent detection of Hg2+ in acomplex environment by conjugating magneticnanoparticles with a triple-helix molecular switch

Jing Zheng, Yuhong Nie, Yaping Hu, Jishan Li, Yinhui Li,Ying Jiang and Ronghua Yang*

In this communication, we molecularly engineered alight-switching excimer oligonucleotide-based probefor fluorescent detection of Hg2+.

This journal is �c The Royal Society of Chemistry 2013 Chem. Commun., 2013, 49, 6817–6826 | 6825

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COMMUNICATIONS

6918

One-step DNA-programmed growth of CpGconjugated silver nanoclusters: a potentialplatform for simultaneous enhanced immuneresponse and cell imaging

Yu Tao, Zhenhua Li, Enguo Ju, Jinsong Ren* andXiaogang Qu*

We designed a one-pot synthesis that allowsCpG-functionalized AgNCs to be prepared,combining attractive features of enhancedimmune response and intracellular imaging.

6826 | Chem. Commun., 2013, 49, 6817–6826 This journal is �c The Royal Society of Chemistry 2013

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