Topics in Current Chemistry

Transcription

1 322 Topics in Current Chemistry Editorial Board: K.N. Houk C.A. Hunter M.J. Krische J.-M. Lehn l l l S.V. Ley M. Olivucci J. Thiem M. Venturi P. Vogel l l l l C.-H. Wong H. Wong H. Yamamoto l l

2 Topics in Current Chemistry Recently Published and Forthcoming Volumes Constitutional Dynamic Chemistry Volume Editor: Mihail Barboiu Vol. 322, 2012 EPR Spectroscopy: Applications in Chemistry and Biology Volume Editors: Malte Drescher, Gunnar Jeschke Vol. 321, 2012 Radicals in Synthesis III Volume Editors: Markus R. Heinrich, Andreas Gansäuer Vol. 320, 2012 Chemistry of Nanocontainers Volume Editors: Markus Albrecht, F. Ekkehardt Hahn Vol. 319, 2012 Liquid Crystals: Materials Design and Self-Assembly Volume Editor: Carsten Tschierske Vol. 318, 2012 Fragment-Based Drug Discovery and X-Ray Crystallography Volume Editors: Thomas G. Davies, Marko Hyvönen Vol. 317, 2012 Novel Sampling Approaches in Higher Dimensional NMR Volume Editors: Martin Billeter, Vladislav Orekhov Vol. 316, 2012 Advanced X-Ray Crystallography Volume Editor: Kari Rissanen Vol. 315, 2012 Pyrethroids: From Chrysanthemum to Modern Industrial Insecticide Volume Editors: Noritada Matsuo, Tatsuya Mori Vol. 314, 2012 Unimolecular and Supramolecular Electronics II Volume Editor: Robert M. Metzger Vol. 313, 2012 Unimolecular and Supramolecular Electronics I Volume Editor: Robert M. Metzger Vol. 312, 2012 Bismuth-Mediated Organic Reactions Volume Editor: Thierry Ollevier Vol. 311, 2012 Peptide-Based Materials Volume Editor: Timothy Deming Vol. 310, 2012 Alkaloid Synthesis Volume Editor: Hans-Joachim Knölker Vol. 309, 2012 Fluorous Chemistry Volume Editor: István T. Horváth Vol. 308, 2012 Multiscale Molecular Methods in Applied Chemistry Volume Editors: Barbara Kirchner, Jadran Vrabec Vol. 307, 2012 Solid State NMR Volume Editor: Jerry C. C. Chan Vol. 306, 2012 Prion Proteins Volume Editor: Jörg Tatzelt Vol. 305, 2011 Microfluidics: Technologies and Applications Volume Editor: Bingcheng Lin Vol. 304, 2011

3 Constitutional Dynamic Chemistry Volume Editor: Mihail Barboiu With Contributions by T. Aastrup M. Barboiu R. Custelcean A. Deratani N. Giuseppone S. Ladame S. Lecommandoux J.-M. Lehn E. Mahon K. Meguellati B.L. Miller E. Moulin G.D. Pantoş N. Ponnuswamy D. Quémener J. Ramírez O. Ramström M. Sakulsombat J.K.M. Sanders A.-M. Stadler A.R. Stefankiewicz Y. Zhang

4 Editor Dr. Mihail Barboiu Institut Européen des Membranes ENSCM-UMII-CNRS 5635 Place Eugene Bataillon CC , Montpellier, Cedex 5 France ISSN e-issn ISBN e-isbn DOI / Springer Heidelberg Dordrecht London New York Library of Congress Control Number: # Springer-Verlag Berlin Heidelberg 2012 This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilm or in any other way, and storage in data banks. Duplication of this publication or parts thereof is permitted only under the provisions of the German Copyright Law of September 9, 1965, in its current version, and permission for use must always be obtained from Springer. Violations are liable to prosecution under the German Copyright Law. The use of general descriptive names, registered names, trademarks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. Printed on acid-free paper Springer is part of Springer Science+Business Media (

5 Volume Editor Dr. Mihail Barboiu Institut Européen des Membranes ENSCM-UMII-CNRS 5635 Place Eugene Bataillon CC , Montpellier, Cedex 5 France Editorial Board Prof. Dr. Kendall N. Houk University of California Department of Chemistry and Biochemistry 405 Hilgard Avenue Los Angeles, CA , USA houk@chem.ucla.edu Prof. Dr. Christopher A. Hunter Department of Chemistry University of Sheffield Sheffield S3 7HF, United Kingdom c.hunter@sheffield.ac.uk Prof. Michael J. Krische University of Texas at Austin Chemistry & Biochemistry Department 1 University Station A5300 Austin TX, , USA mkrische@mail.utexas.edu Prof. Dr. Jean-Marie Lehn ISIS 8, allée Gaspard Monge BP Strasbourg Cedex, France lehn@isis.u-strasbg.fr Prof. Dr. Steven V. Ley University Chemical Laboratory Lensfield Road Cambridge CB2 1EW Great Britain Svl1000@cus.cam.ac.uk Prof. Dr. Massimo Olivucci Università di Siena Dipartimento di Chimica Via A De Gasperi Siena, Italy olivucci@unisi.it Prof. Dr. Joachim Thiem Institut für Organische Chemie Universität Hamburg Martin-Luther-King-Platz Hamburg, Germany thiem@chemie.uni-hamburg.de Prof. Dr. Margherita Venturi Dipartimento di Chimica Università di Bologna via Selmi Bologna, Italy margherita.venturi@unibo.it

6 vi Editorial Board Prof. Dr. Pierre Vogel Laboratory of Glycochemistry and Asymmetric Synthesis EPFL Ecole polytechnique féderale de Lausanne EPFL SB ISIC LGSA BCH 5307 (Bat.BCH) 1015 Lausanne, Switzerland Prof. Dr. Chi-Huey Wong Professor of Chemistry, Scripps Research Institute President of Academia Sinica Academia Sinica 128 Academia Road Section 2, Nankang Taipei 115 Taiwan Prof. Dr. Henry Wong The Chinese University of Hong Kong University Science Centre Department of Chemistry Shatin, New Territories Prof. Dr. Hisashi Yamamoto Arthur Holly Compton Distinguished Professor Department of Chemistry The University of Chicago 5735 South Ellis Avenue Chicago, IL USA

7 Topics in Current Chemistry Also Available Electronically Topics in Current Chemistry is included in Springer s ebook package Chemistry and Materials Science. If a library does not opt for the whole package the book series may be bought on a subscription basis. Also, all back volumes are available electronically. For all customers with a print standing order we offer free access to the electronic volumes of the series published in the current year. If you do not have access, you can still view the table of contents of each volume and the abstract of each article by going to the SpringerLink homepage, clicking on Chemistry and Materials Science, under Subject Collection, then Book Series, under Content Type and finally by selecting Topics in Current Chemistry. You will find information about the Editorial Board Aims and Scope Instructions for Authors Sample Contribution at springer.com using the search function by typing in Topics in Current Chemistry. Color figures are published in full color in the electronic version on SpringerLink. Aims and Scope The series Topics in Current Chemistry presents critical reviews of the present and future trends in modern chemical research. The scope includes all areas of chemical science, including the interfaces with related disciplines such as biology, medicine, and materials science. The objective of each thematic volume is to give the non-specialist reader, whether at the university or in industry, a comprehensive overview of an area where new insights of interest to a larger scientific audience are emerging. vii

8 viii Topics in Current Chemistry Also Available Electronically Thus each review within the volume critically surveys one aspect of that topic and places it within the context of the volume as a whole. The most significant developments of the last 5 10 years are presented, using selected examples to illustrate the principles discussed. A description of the laboratory procedures involved is often useful to the reader. The coverage is not exhaustive in data, but rather conceptual, concentrating on the methodological thinking that will allow the nonspecialist reader to understand the information presented. Discussion of possible future research directions in the area is welcome. Review articles for the individual volumes are invited by the volume editors. In references Topics in Current Chemistry is abbreviated Top Curr Chem and is cited as a journal. Impact Factor 2010: 2.067; Section Chemistry, Multidisciplinary : Rank 44 of 144

9 Preface Constitutional Dynamic Chemistry (CDC) and its application Dynamic Combinatorial Chemistry (DCC) are new evolutional approaches to produce chemical diversity. In contrast to the classical methods, they allow for the simple generation of functional systems amplified from a mixture of inter-exchanging architectures which result from sets of building blocks interacting reversibly. Kinetic or thermodynamic resolution, self-assembly followed by covalent modification, and phase-change processes all shed light on useful strategies to control and create convergence between self-organization and constitutional functions. Such dynamic libraries have special relevance for a very diverse range of applications such as drug-, catalyst-, and material discovery. CDC implements a dynamic molecular/ supramolecular reversible interface between interacting constituents, mediating the structural self-correlation of different domains of generated systems by virtue of their basic constitutional behaviors. The self-assembly of the components controlled by mastering molecular/supramolecular interactions may allow the flow of structural information from molecular level toward nanoscale dimensions. This volume of Topics in Current Chemistry focuses on constitutional methods for understanding and controlling such upscale propagation of structural information. These methods show potential to impose further precise order at the mesoscale and to discover new routes to obtain highly ordered ultradense arrays over macroscopic distances. During the last decade, CDC has become increasingly interesting for Dynamic Interactive Systems (DIS). Networks of continuously exchanging and reversibly reorganizing objects form the core of DIS. For example, molecules, supermolecules, polymers, biomolecules, biopolymers, nanotubes, surfaces, nanoparticles, liposomes, materials, and cells are all operating under the natural selection to allow spatial/temporal and structural/functional adaptability in response to constitutional internal or stimulant external factors. The contributions to this volume open new horizons, shortening the essential steps from molecular to functional nano-objects. These steps are sometimes too long and the research strategies should expand the fundamental understanding of complex dynamic structures and properties as it relates to creating products and manufacturing processes. Combined ix

10 x Preface dynamic strategies to produce constitutional/combinatorial systems can be effectively shared as soon merged marketable technology to benefit most research laboratories and industrial producers. The 11 chapters are structured in three groups: 1. Evolutional Approaches to Produce Chemical Diversity and the Development of the Constitutional Dynamic Systems (Lehn, Miller, Ramström et al., and Ladame), 2. Constitutional Self-Assembly Toward Complex Architectures (Pantos and Sanders, Custelcean, and Quemener et al.), and 3. Constitutional Dynamic Chemistry Toward Dynamic Interactive Systems (Barboiu, Mahon et al., Giussepone et al., and Stadler et al.). I would like to thank all the authors, as well as all those who have facilitated this volume, and I hope that readers will find answers to key questions concerning basic principles and related evolutional approaches that have been used in Constitutional Dynamic Chemistry (CDC). The most revolutionary consequences may reflect the fascinating possibilities offered by selection, evolution, amplification, molecular recognition, and replication processes. This volume is not a comprehensive treatise, but is a timely objective snapshot of the CDC field from which the reader can get a broader insight into this and hopefully a future source of inspiration. Montpellier Mihail Barboiu.

11 Contents Constitutional Dynamic Chemistry: Bridge from Supramolecular Chemistry to Adaptive Chemistry... 1 Jean-Marie Lehn Multistate and Phase Change Selection in Constitutional Multivalent Systems Mihail Barboiu Dynamic Systemic Resolution Morakot Sakulsombat, Yan Zhang, and Olof Ramström Dynamic Combinatorial Self-Replicating Systems Emilie Moulin and Nicolas Giuseppone DCC in the Development of Nucleic Acid Targeted and Nucleic Acid Inspired Structures Benjamin L. Miller Dynamic Nanoplatforms in Biosensor and Membrane Constitutional Systems Eugene Mahon, Teodor Aastrup, and Mihail Barboiu Dynamic Assembly of Block-Copolymers D. Quémener, A. Deratani, and S. Lecommandoux Dynamic Chemistry of Anion Recognition Radu Custelcean Supramolecular Naphthalenediimide Nanotubes Nandhini Ponnuswamy, Artur R. Stefankiewicz, Jeremy K. M. Sanders, and G. Dan Pantoş xi

12 xii Contents Synthetic Molecular Machines and Polymer/Monomer Size Switches that Operate Through Dynamic and Non-Dynamic Covalent Changes Adrian-Mihail Stadler and Juan Ramírez Reversible Covalent Chemistries Compatible with the Principles of Constitutional Dynamic Chemistry: New Reactions to Create More Diversity Kamel Meguellati and Sylvain Ladame Index