Perspectives in Supramolecular Chemistry: Supramolecular Materials and Technologies, Volume 4

316 Pages·1999·13.235 MB·English

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 ([phone]
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.