MACROCYCLIC CHEMISTRY

Transcription

1 MACROCYCLIC CHEMISTRY

2 Macrocyclic Chemistry Current Trends and Future Perspectives Edited by KARSTEN GLOE Technische Universität Dresden, Germany

3 A C.I.P. Catalogue record for this book is available from the Library of Congress. ISBN (HB) Springer Dordrecht, Berlin, Heidelberg, New York ISBN (e-book) Springer Dordrecht, Berlin, Heidelberg, New York ISBN (HB) Springer Dordrecht, Berlin, Heidelberg, New York ISBN (e-book) Springer Dordrecht, Berlin, Heidelberg, New York Published by Springer, P.O. Box 17, 3300 AA Dordrecht, The Netherlands. The front cover illustration depicts the X-ray structure of 5,10,15,20-(4-bromophenyl)-21,23- dithiaporphyrin obtained by S. Stute and T. Söhnel, TU Dresden. The image on the back cover and in the preface shows the logo of the ISMC 2005 in Dresden designed by Cornelia Kreiß, TU Dresden. Printed on acid-free paper All Rights Reserved 2005 Springer No part of this work may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, microfilming, recording or otherwise, without written permission from the Publisher, with the exception of any material supplied specifically for the purpose of being entered and executed on a computer system, for exclusive use by the purchaser of the work. Printed in the Netherlands.

4 CONTENTS PREFACE ix 1 CONTRIBUTIONS OF THE INTERNATIONAL SYMPOSIUM ON MACROCYCLIC CHEMISTRY TO THE DEVELOPMENT OF MACROCYCLIC CHEMISTRY R. M. Izatt, K. Pawlak and J. S. Bradshaw 1 2 FROM FUNCTIONALISED CATENANES, ROTAXANES AND KNOTS TO HIGHER INTERTWINED ASSEMBLIES O. Lukin and F. Vögtle 15 3 TOWARDS FUNCTIONAL MACROCYCLES: SELF-ASSEMBLY AND TEMPLATE STRATEGIES C. A. Schalley, H. T. Baytekin and B. Baytekin 37 4 RECENT DEVELOPMENTS IN THE SYNTHESIS AND d-block CHEMISTRY OF LINKED MULTI-RING MACROCYCLIC LIGANDS L. F. Lindoy 53 5 BINDING AND STRUCTURAL ASPECTS OF NITRILE- AND AMINO- FUNCTIONALISED PENDANT ARM DERIVATIVES OF 1,4,7- TRIAZACYCLONONANE ([9]aneN3) M. Schröder and V. Lippolis 67 6 AZAMACROCYCLIC SYSTEMS WITH DIFFERENT SUPRAMOLECULAR FUNCTIONS B. König and J. Svoboda 87 7 SENSING, TEMPLATION AND SELF-ASSEMBLY BY MACROCYCLIC LIGAND SYSTEMS P. D. Beer and W. W. H. Wong SIGNALLING REVERSIBLE ANION BINDING IN AQUEOUS MEDIA R. S. Dickens and D. Parker ION-PAIR RECOGNITION BY DITOPIC MACROCYCLIC RECEPTORS B. D. Smith CYCLIC AND ACYCLIC AMIDOPYRROLE CONTAINING ANION RECEPTORS S. J. Brooks and P. A. Gale 153 v

5 vi MACROCYCLIC CHEMISTRY 11 STRUCTURAL ASPECTS OF HALIDES WITH CRYPTANDS MD. A. Hossain, S. O. Kang and K. Bowman-James OXOANION SELECTIVITY WITH PROTONATED AZACRYPTATE HOSTS: THE INFLUENCE OF HYDRATION ON STRUCTURE AND STABILITY J. Nelson, V. McKee and R. M. Town CYCLODEXTRIN COMBINATIONS WITH AZOCOMPOUNDS E. Luboch, Z. Poleska-Muchlado, M. Jamrógiewicz and J. Biernat Ru(II) AND Os(II) COMPLEXES OF A SHAPE-PERSISTENT MACROCYCLIC LIGAND: SYNTHESIS, PHOTOPHYSICAL PROPERTIES, AND ELECTROCHEMICAL CHARACTERIZATION M. Venturi, V. Balzani, F. Marchioni, D. M. Opris, P. Franke and A.-D. Schlüter MACROCYCLIC SYSTEMS WITH PHOTOSWITCHABLE FUNCTIONS O. A. Fedorova, E. N. Ushakov, Y. V. Fedorov, Y. P. Strokach and S. P. Gromov MODEL SYSTEMS FOR BIOLOGICAL PROCESSES G. W. Gokel, W. M. Leevy and M. E. Weber RECOGNITION OF CYTOCHROME c BY TETRAPHENYLPORPHYRIN- BASED PROTEIN SURFACE RECEPTORS R. K. Jain, L. K. Tsou and A. D. Hamilton SUPRAMOLECULAR COMPLEXES WITH MACROCYCLES: SURPRISES AND INSIGHTS H.-J. Schneider CALORIMETRY: AN INDISPENSIBLE TOOL IN THE DESIGN OF MOLECULAR HOSTS F. P. Schmidtchen MODELING OF MACROCYCLIC LIGAND COMPLEXES P. Comba and B. Martin SIMULATIONS OF THE DYNAMICS OF 18-CROWN-6 AND ITS COMPLEXES: FROM THE GAS PHASE TO AQUEOUS INTERFACES WITH SC-CO 2 AND A ROOM-TEMPERATURE IONIC LIQUID A. Chaumont, R. Schurhammer, P. Vayssière and G. Wipff APPLICATION OF MACROCYCLIC LIGANDS TO ANALYTICAL CHROMATOGRAPHY J. D. Lamb and J. S. Gardner 349

6 MACROCYCLIC CHEMISTRY vii 23 LIGAND DESIGN FOR BASE METAL RECOVERY P. A. Tasker and V. Gasperov USE OF MACROCYCLES IN NUCLEAR-WASTE CLEANUP: A REAL- WORLD APPLICATION OF A CALIXCROWN IN CESIUM SEPARATION TECHNOLOGY B. A. Moyer, J. F. Birdwell, Jr., P. V. Bonnesen and L. H. Delmau TEXAPHYRIN CONJUGATES. PROGRESS TOWARDS SECOND GENERATION DIAGNOSTIC AND THERAPEUTIC AGENTS W.-H. Wei, M. E. Fountain, J. L. Sessler, D. J. Magda, Z. Wang and Richard A. Miller 407 APPENDIX: COLOURED FIGURES OF CHAPTERS 3, 7, 8, 11, 12, 17, 21, 23, INDEX 441

7 PREFACE Macrocyclic and supramolecular chemistry have developed into one of the most active and promising research areas of chemical science located at the interface between chemistry, physics and biology. Based on the pioneering and stimulating work of the 1987 Nobel Prize Winners Charles J. Pedersen, Donald J. Cram and Jean-Marie Lehn, this field encompasses manifold fundamental aspects of molecular recognition and selforganization and uses these biological principles for the design of smart artificial systems. Therefore an enormous potential exists (some of which is currently being exploited) for future applications in such fields as bio- and nanotechnology, environmental protection, catalysis, molecular electronics and photonics as well as medicine. The interdisciplinary character of supramolecular chemistry thus provides a platform for the mixing and cross-pollination of ideas between chemists, physicists, biologists and engineers. Since the first International Symposium on Macrocyclic Chemistry (ISMC) was held at Brigham Young University in Provo, USA in 1977, the yearly conferences have been a forum for experts in supramolecular chemistry, bringing together researchers from around the globe in a pleasant and creative atmosphere. In July 2005 the XXX ISMC conference will be held in Dresden, Germany. In order to celebrate the 30 th meeting, it was the idea of Emma Roberts from Kluwer Academic Publishers to produce a book in which selected aspects of current macrocyclic and supramolecular chemistry would be highlighted. Owing to the enormous number of publications that continue to appear, it has been a difficult venture to cover all important facets of this expanding field. Nevertheless, the result of our efforts and of the hard work of 25 leading groups in the field is now presented to you. Starting with a discussion of the history of ISMC, the following chapters serve to characterize a representative number of topics in macrocyclic chemistry and to indicate its future developments. Thus, the synthesis, structure and properties of functional macrocycles, their modeling and an outlook towards their possible application, such as for monitoring, environmental clean-up and recovery, in medicine or as models for biological processes, are all presented. I am indebted to all the authors for their stimulating contributions and for their commitment and patience during the very short preparation time for the chapters between April and October I should like to thank my coworkers, especially Marco Wenzel, Christoph Naumann and my wife, Kerstin, who have helped me complete this book by reading and correcting the manuscripts. In particular, I am very grateful to Bianca Antonioli who fostered close contact with the authors and who had the tremendous burden of coming to grips with the formatting of the individual chapters. Karsten Gloe (ed.), Macrocyclic Chemistry: Current Trends and Future Perspectives, ix x Springer. Printed in the Netherlands.

8 x MACROCYCLIC CHEMISTRY Finally, I sincerely thank Emma Roberts and Vaska Krabbe from Springer (formerly Kluwer Academic Publishers) for their considerable assistance during preparation of the book. Hopefully this book will find a timely and useful place in the supramolecular chemistry community. Dresden, Germany October 2004 Karsten Gloe