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Organic Photochemistry and Photophysics PDF

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Organic Photochemistry and Photophysics MOLECULAR AND SUPRAMOLECULAR PHOTOCHEMISTRY Series Editors V.Ramamurthy Professor Department of Chemistry University of Miami Miami,Florida Kirk S.Schanze Professor Department of Chemistry University of Florida Gainesville,Florida 1. Organic Photochemistry, edited by V.Ramamurthy and Kirk S.Schanze 2. Organic and Inorganic Photochemistry, edited by V.Ramamurthy and Kirk S.Schanze 3. Organic Molecular Photochemistry, edited by V.Ramamurthy and Kirk S.Schanze 4. Multimetallic and Macromolecular Inorganic Photochemistry, edited by V.Ramamurthy and Kirk S.Schanze 5. Solid State and Surface Photochemistry, edited by V.Ramamurthy and Kirk S.Schanze 6. Organic, Physical, and Materials Photochemistry, editedby V.Ramamurthy and Kirk S.Schanze 7. Optical Sensors and Switches, edited by V.Ramamurthy and Kirk S.Schanze 8. Understanding and Manipulating Excited-State Processes, edited by V.Ramamurthy and Kirk S.Schanze 9. Photochemistry of Organic Molecules in Isotropic and Anisotropic Media,edited by V.Ramamurthy and Kirk S.Schanze 10. Semiconductor Photochemistry and Photophysics, edited by V.Ramamurthy and Kirk S.Schanze 11. Chiral Photochemistry, edited by Yoshihisa Inoue and V.Ramamurthy 12. Synthetic Organic Photochemistry, edited by Axel G.Griesbeck and Jochen Mattay 13. Computational Methods in Photochemistry, edited by Andrei G.Kutateladze 14. Organic Photochemistry and Photophysics, edited by V.Ramamurthy and Kirk S.Schanze Organic Photochemistry and Photophysics edited by Vaidhyanathan Ramamurthy University of Miami Miami, Florida Kirk Schanze University of Florida Gainesville, Florida Boca Raton London New York A CRC title, part of the Taylor & Francis imprint, a member of the Taylor & Francis Group, the academic division of T&F Informa plc. Published in 2006 by CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2006 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group No claim to original U.S. Government works Printed in the United States of America on acid-free paper 10 9 8 7 6 5 4 3 2 1 International Standard Book Number-10: 0-8493-7608-4 (Hardcover) International Standard Book Number-13: 978-0-8493-7608-5 (Hardcover) This book contains information obtained from authentic and highly regarded sources. Reprinted material is quoted with permission, and sources are indicated. A wide variety of references are listed. Reasonable efforts have been made to publish reliable data and information, but the author and the publisher cannot assume responsibility for the validity of all materials or for the consequences of their use. No part of this book may be reprinted, reproduced, transmitted, or utilized in any form by any electronic, mechanical, or other means, now known or hereafter invented, including photocopying, microfilming, and recording, or in any information storage or retrieval system, without written permission from the publishers. For permission to photocopy or use material electronically from this work, please access www.copyright.com (http://www.copyright.com/) or contact the Copyright Clearance Center, Inc. (CCC) 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400. CCC is a not-for-profit organization that provides licenses and registration for a variety of users. For organizations that have been granted a photocopy license by the CCC, a separate system of payment has been arranged. Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and explanation without intent to infringe. Library of Congress Cataloging-in-Publication Data Catalog record is available from the Library of Congress Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com Taylor & Francis Group and the CRC Press Web site at is the Academic Division of Informa plc. http://www.crcpress.com Preface Photochemistry is vital to the survival of life on Earth. Light-triggered events serve primary functions in various biological events. The role of light in materials science needs no emphasis, and the value of solar energy has never been more evident than now. Photochemistry is no longer a discipline practiced by a few who are interested in understanding the excited state photochemistry and photophysics of selected molecules. The concepts of photochemistry have pervaded various disciplines, and research in this area is pursued not only by photochemists but also by physical organic chemists, chemical physicists, biologists, materials scientists, and industrial chemists. This volume contains seven chapters written by international experts on the photochemistry and photophysics of organic, inorganic, and biological molecules. The fi rst chapter by Steer and coworkers summarizes the current status of upper excited state physics of organic and inorganic molecules. Almost fi ve decades ago it was believed that no measurable processes are likely from S, S, T, and T states; 2 3 2 3 however, Chapter 1 makes it evident that this belief is no longer valid. Excited state proton transfer has been known and investigated for almost four decades. Recent developments in pico and femto second spectroscopy have revived interest on this topic. In Chapter 2, Shizuka and Tobita summarize recent advances in excited state proton transfer. Organic photochemistry deals with exploring and generalizing the excited state behavior of various chromophores. Excited state behavior of most other chromophores is understood on the basis of carbonyls, olefi ns, enones, and aromatics, which have played leading roles in this process. In Chapter 3, Nau and Pischel highlight the excited state behavior of azoakanes by comparing them directly with alkanones. Photosubstitution reactions of aromatics could become very useful synthetic reactions provided all we know about them is understood in terms of simple models, as discussed by Fagnoni and Albini in Chapter 4. Two of the most fundamental processes in chemistry are electron and proton transfer. Electron transfer has received considerable attention during the last two decades. In Chapters 5 and 6, Yoon, Yasuda, and coworkers, who have made fundamental contributions to electron transfer photochemistry, summarize their work on photoamination of olefi ns and photocyclization of phthalimides, two of the most synthetically useful reactions. In Chapter 7, Armitage discusses a fascinating area of current research in photochemical sciences, namely, aggregation of cynanine and porphyrin dyes. In this chapter, factors that lead to controlled assembly of dyes on DNA surfaces are presented. The volumes in this series serve the needs of chemists who have interest in using light to control the excited state chemistry of organic, inorganic, and biological molecules. It is believed that the chapters in this volume will serve not only experts but also as supplementary reading material in graduate courses. Contributors Angelo Albini Department of Organic Chemistry University of Pavia Pavia, Italy Bruce A. Armitage Department of Chemistry Carnegie Mellon University Pittsburgh, Pennsylvania G. Burdzinski Quantum Electronics Laboratory Faculty of Physics Adam Mickiewicz University Poznan, Poland Maurizio Fagnoni Department of Organic Chemistry University of Pavia Pavia, Italy J. Kubicki Quantum Electronics Laboratory Faculty of Physics Adam Mickiewicz University Poznan, Poland A. Maciejewski Photochemistry Laboratory Faculty of Chemistry and Center for Ultrafast Laser Spectroscopy Adam Mickiewicz University Poznan, Poland Patrick S. Mariano Department of Chemistry University of New Mexico Albuquerque, New Mexico Jin Matsumoto Department of Chemical Science and Engineering Miyakonojo National College of Technology Miyakonojo, Miyazaki, Japan Werner M. Nau School of Engineering and Science International University of Bremen Bremen, Germany Uwe Pischel Department of Chemistry Faculty of Sciences University of Porto Porto, Portugal Kensuke Shima Department of Chemical Science and Engineering Miyakonojo National College of Technology Miyakonojo, Miyazaki, Japan Tsutomu Shiragami Department of Chemical Science and Engineering Miyakonojo National College of Technology Miyakonojo, Miyazaki, Japan Haruo Shizuka Gunma University Kiryu, Japan R.P. Steer Department of Chemistry University of Saskatchewan Saskatoon, Saskatchewan, Canada Seiji Tobita Gunma University Kiryu, Japan S. Velate Department of Chemistry University of Saskatchewan Saskatoon, Saskatchewan, Canada Toshiaki Yamashita Department of Chemical Science and Engineering Miyakonojo National College of Technology Miyakonojo, Miyazaki, Japan Masahide Yasuda Department of Applied Chemistry Faculty of Engineering University of Miyazaki Gakuen-Kibanadai, Miyazaki, Japan E.K.L. Yeow Department of Chemistry University of Saskatchewan Saskatoon, Saskatchewan, Canada Ung Chan Yoon Department of Chemistry College of Natural Sciences Pusan National University Pusan, Korea

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