Perspectives in Supramolecular Chemistry: Supramolecular Materials and Technologies, Volume 4 PDF
Preview Perspectives in Supramolecular Chemistry: Supramolecular Materials and Technologies, Volume 4
Supramolecular Materials and Technologies Editorial Board Founding Editor J.-M. Lehn, College de France, Chimie des Interactions Moleculaires, 11 Place Marcelin Berthelot, 75005 Paris, France Editors J.-P. Behr, Universite Louis Pasteur, Institut le Bel, 4 Rue Blaise Pascal, F-67070, Strasbourg, France G. R. Desiraju, University of Hyderabad, School of Chemistry, Hyderabad 500134, India A. D. Hamilton, Yale University, Department of Chemistry, New Haven, CT 06520- 8107, USA T. Kunitake, Kyushu University, Faculty of Engineering, Hakozaki, Fukuoka 8 I 2, Japan D. N. Reinhoudt, University of Twente, Faculty of Chemical Technology, PO Box 217, 7500 AE Enschede, The Netherlands J.-P-Sauvage, Universitk Louis Pasteur, Institut le Bel, 4 Rue Blaise Pascal, F-67070 Strasbourg, France Supramolecular Materials and Technologies Perspectives in Supramolecular Chemistry Volume 4 EDITEDB Y DAVIDN . REINHOUDT University of Twente, Department of Chemistty, Enschede, The Netherlandb JOHN WILEY & SONS Chichester . New York . Weinheim . Brisbane . Toronto . Singapore Copyright 0 1999 John Wiley & Sons Ltd, Baffins Lane, Chichester, West Sussex PO19 IUD, England National 01243 779777 International (+44) 1243 779777 e-mail (for orders and customer service enquiries): [email protected] Visit our Home Page on http://ww.wiley.co.uk or http://www.wiley.com All Rights Reserved. No part of this publication may be reproduced, storcd in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording, scanning or otherwise, except under the terms of the Copyright, Designs and Patents Act 1988 or under the terms of a licence issued by the Copyright Licensing Agency, 90 Tottenham Court Road, London WIP 9HE, UK, without the permission in writing of the publisher. Other Wiley Editorial Ofices John Wiley & Sons, Inc., 605 Third Avenue, New York, NY 10158-0012, USA WILEY-VCH Verlag GmbH, Pappelallee 3, D-69469 Weinheim, Germany Jacaranda Wiley Ltd, 33 Park Road Milton, Qneensland 4064, Australia John Wiley Sons (Asia) Pte Ltd, Clementi Loop #02-01, Jim Xing Distripark, Singapore 129809 Wiley & Sons (Canada) Ltd, 22 Worcester Road, John Rexdale, Ontario M9W ILI, Canada Library of Congress Cataloging-in-Publication Data Supramolecular materials and technologies / edited by David N. Reinhoudt. p. cm. - (Perspectives in supramolecular chemistry : v. 4) Includes bibliographical references and indexes. ISBN 0-471-97367-X (hb : alk. paper) 1. Macromolecules. 1. Reinhoudt, D. N. 11. Series. QD381.S87 1999 99- 1899 1 547’.7-d~21 CIP British Library Cataloguing in Publication Data A catalogue record for this book is available from the British Library ISBN 0-471-97367-X Typeset in 10/ 12pt Times by Techset Composition Ltd, Salisbury, Wiltshire Printed and bound in Great Britain by Biddles Ltd, Guildford and King’s Lynn This book is printed on acid-free paper responsibly manufactured from sustainable forestation, for which at least two trees are planted for each one used for paper production, Contents Contributors vii Preface ix 1 Self-Assembling Systems on Scales from Nanometers to Millimeters: Design and Discovery Lyle Issacs, Donovan N. Chin, Ned Bowden, Younan Xia and George M. Whitesides 1 2 Dendritic Architectures Marcel H. P. van Genderen and E. W. Meijer 47 3 Supramolecular Structures with Macromolecules Uwe Beginn and Martin Moller 89 4 Chemosensors: Synthetic Receptors in Analytical Sensing Applications Anthony W. Czarnik and Juyoung Yoon 177 5 Selective Ion Recognition with Durable Sensors Ronny J. W. Lugtenberg and David N. Reinhoudt 193 6 Ion Separations in Membrane and Solid Phase Extraction Systems Reed M. Izatt, Jerald S. Bradshaw and Ronald L. Bruening 225 7 Porphyrin- and Expanded Porphyrin-based diagnostic and therapeutic agents Tar& D. Mody and Jonathan L. Sessler 245 vi Contents Cumulative Author Index 295 Cumulative Title Index 299 Index 301 Contributors Uwe Beginn, Universitat Ulm Abteilung Organische Chemie IJI/Makromolekulare Chemie, Albert-Einstein-Allee 1 1, D-89069 Ulrn, Germany Ned Bowden, Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138, USA Jerald S. Bradshaw, Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT 84602, USA Ronald L. Bruening, IBC Advanced Technologies Inc., American Fork, UT 84003, USA Donovan N. Chin, Moldyn Inc, 955 Massachusetts Avenue, Cambridge, MA 02139, USA Anthony W. Czarnik, Illumina, 9390 Towne Centre Drive, STE 200, San Diego, CA 92121-3015, USA Lyle Issaes, Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02 138, USA Reed M. Izatt, Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT 84602, USA Ronny J. W. Lugtenberg, Laboratory of Supramolecular Chemistry and Technology and MESA Research Institute, University of Twente, PO Box 217, 7500 AE Enschede, The Netherlands ... Vlll Contributors E. W. Meijer, Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, PO Box 513, 5600 MB Eindhoven, The Netherlands Tarak D. Mody, Pharmacyclics Inc., 995E. Arques Ave. Sunnyvale, CA 94086, USA Martin Moller, Universitat Ulm, Abteilung Organische Chemie III/ Makromolekulare Chemie, Albert-Einstein-Allee 1 1, D-89069 Ulm, Germany David N. Reinhoudt, Laboratory of Supramolecular Chemistry and Technology and MESA Research Institute, University of Twente, PO Box 217, 7500 AE Enschede, The Netherlands Jonathan L. Sessler, The University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, TX 78712, USA Marcel H. P. Van Genderen, Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, PO Box 513, 5600 MB Eindhoven, The Netherlands George M. Whitesides, Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138, USA Younan Xia, Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138, USA Juyoung Yoon, Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037. USA Preface From the early days of supramolecular chemistry the field has been associated with possible applications. This is not surprising as the design of new molecules, and later of assemblies of molecules, is often function driven. Now, after three decades of supramolecular chemistry, it is interesting to reflect on what has really been achieved in terms of applications. This is the field that I have defined as Supramolecular Technology. In the beginning molecular recognition was the objective. From this work on receptors that selectively recognize ionic species, the first applications are now established technologies. They can be found in analytical chemistry, in separation science and in the medical world. Chapters 4 to 7 deal with the various aspects of these technologies. In more recent years there is a development towards molecular recognition as a tool. Based on the increasing understanding of the weak forces between (macro) molecules we now see new concepts of material design. Chapters 1 to 3 cover three aspects of this development: nanostructures that are formed by self-assembly of small molecules (chapter 1) , dendritic structures (chapter 2) and polymers (chapter 3). A volume of a series like Perspectives in Supramolecular Chemistry can never claim to cover all aspects of a subject. All I can hope is that these chapters are representative of the filed of supramolecular technology. David N. Reinhoudt Ensckede Chapter 1 Self-assembling Systems on Scales from Nanometers to Millimeters: Design and Discovery LYLEI SAACS*, DONOVANN . CHIN?, NED BOWDEN*Y, OUNAN XIA*, AND GEORGEM . WHITESIDES* * Haward University, MA, USA tMoidyn Inc., Cambridge, MA, USA 1. INTRODUCTION Self-assembly is the spontaneous organization of molecules or objects into stable aggregates by noncovalent forces [ 1-51. Self-assembly is especially evident in biology and much of the early inspiration for studies of self-assembly came from biological aggregates: lipid bilayers, viral capsids, the DNA duplex, and the tertiary and quaternary structure of proteins [6-81. Chemists have been exploring self- assembly as an alternative to the powerful, but stepwise, methods of synthetic chemistry [2,9-271. Self-assembly is interesting both for its biological relevance, and because it is a new approach to complex structures having nanometer to millimeter dimensions that are difficult or impossible to prepare by traditional techniques. Figure 1 shows a scale fiom 1 nm to 10 mm; several examples of natural systems and their corresponding sizes are shown above the scale. Below the scale are pictures of four self-assembling systems that have been investigated in this group, namely hydrogen bonded self-assembled aggregates both in solution and the solid state, patterned self-assembled monolayers (SAMs) of alkanthiolates on gold, and milli- Suprarnoleculur Technology Edited by David N. Keinhoudt 0 1999 John Wiley & Sons Ltd.
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