Conjugated Polymers: Perspective, Theory, and New Materials PDF
Preview Conjugated Polymers: Perspective, Theory, and New Materials
Conjugated Polymers Perspective, Theory, and New Materials Conjugated Polymers Perspective, Theory, and New Materials Edited by John R. Reynolds, Barry C. Thompson, and Terje A. Skotheim Cover art by Ellen Skotheim. A collage, based on images from important developments in conducting polymers as represented by the 4th edition of the Handbook. CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2019 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S. Government works Printed on acid-free paper International Standard Book Number-13: 978-1-138-06569-7 (Hardback) This book contains information obtained from authentic and highly regarded sources. Reasonable efforts have been made to pub- lish reliable data and information, but the author and publisher cannot assume responsibility for the validity of all materials or the consequences of their use. The authors and publishers have attempted to trace the copyright holders of all material reproduced in this publication and apologize to copyright holders if permission to publish in this form has not been obtained. If any copyright material has not been acknowledged please write and let us know so we may rectify in any future reprint. Except as permitted under U.S. Copyright Law, 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.copy- right.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. Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com Contents Authors ....................................................................................................................vii Contributors .............................................................................................................ix 1 Early History of Conjugated Polymers: From Their Origins to the Handbook of Conducting Polymers ..................................................................1 Seth C. Rasmussen 2 Recent Advances in the Computational Characterization of π-Conjugated Organic Semiconductors. ......................................................... 37 Jean-Luc Brédas, Xiankai Chen, Thomas Körzdörfer, Hong Li, Chad Risko, Sean M. Ryno, and Tonghui Wang 3 Perspective on the Advancements in Conjugated Polymer Synthesis, Design, and Functionality over the Past Ten Years ......................................107 Brian Schmatz, Robert M. Pankow, Barry C. Thompson, and John R. Reynolds 4 Advances in Discrete Length and Fused Conjugated Oligomers .................149 Shanshan Chen, So-Huei Kang, Sang Myeon Lee, Tanya Kumari, and Changduk Yang 5 Direct (Hetero)Arylation Polymerization for the Preparation of Conjugated Polymers .....................................................................................195 J. Terence Blaskovits and Mario Leclerc 6 Living Polymerizations of π-Conjugated Semiconductors .......................... 239 Jeffrey Buenaflor and Christine Luscombe 7 Controlled Synthesis of Polyfurans, Polyselenophenes, and Polytellurophenes .......................................................................................... 263 Shuyang Ye, Emily L. Kynaston, and Dwight S. Seferos 8 Donor-Acceptor Polymers for Organic Photovoltaics ................................. 283 Desta Gedefaw and Mats R. Andersson 9 Conjugated Polymers for n- and p-Type Charge Transport ........................ 325 Zachary S. Parr, Zhijie Guo, and Christian B. Nielsen 10 Conjugated Block Copolymers: Synthesis, Self-Assembly, and Device Applications. ..................................................................................................429 Jessica Shaw and Malika Jeffries-EL v vi Contents 11 Metal-Containing Conjugated Polymers ......................................................447 Christopher M. Brown and Michael O. Wolf 12 Recent Progress in the Development of Optoelectronic Materials Based on Group 13 Element-Containing Conjugated Polymers ............................. 489 Shunichiro Ito, Masayuki Gon, Kazuo Tanaka, and Yoshiki Chujo 13 Multifunctional Conjugated Polymers: Helically Assembled Spherulites, Photo-Controllable Illuminants, and Helical Graphites ..............................517 Kazuo Akagi 14 Conjugated Polyelectrolytes Designed for Biological Applications ............ 547 Pradeepkumar Jagadesan, Yun Huang, and Kirk S. Schanze 15 Oxidative Chemical Vapor Deposition for Conjugated Polymers: Theory and Applications. .............................................................................. 587 Karen K. Gleason and Xiaoxue Wang 16 Flow Synthesis: A Better Way to Conjugating Polymers? .............................613 James H. Bannock, Martin J. Heeney, and John C. de Mello Index ............................................................................................................653 ENDORSEMENTS ENDORSEMENTS Authors John R. Reynolds, a native Californian, obtained his B.S. in Chemistry at San Jose State University (1979) followed by his M.S. (1982) and Ph.D. (1984) in Polymer Science and Engineering at the University of Massachusetts. He became interested in the field of conducting and electroactive polymers through a position with the IBM Research Laboratories in the late 1970s. After developing his own research effort at the University of Texas at Arlington (1984–1991), he moved to the University of Florida where he was a Professor of Chemistry and Associate Director of the Center for Macromolecular Science and Engineering until Spring 2012, when his group moved to Georgia Tech and where he is currently a Professor of Chemistry and Biochemistry, and Materials Science and Engineering. He serves as Director of the Georgia Tech Polymer Network (GTPN) and is a member of the Center for Organic Photonics and Electronics (COPE) management team. Barry C. Thompson was born in Milwaukee, Wisconsin, in 1977 and moved at a young age to Gallipolis, Ohio, where he attended elementary and high school. Barry then attended the University of Rio Grande in Rio Grande, Ohio, where he majored in Chemistry and Physics and minored in Mathematics. After completing his undergraduate studies at Rio Grande, Barry moved to the University of Florida to pur- sue a Ph.D. in Chemistry with Prof. John R. Reynolds as an NSF Graduate Research Fellow. During his Ph.D. studies, Barry focused on the design and synthesis of electroactive conjugated polymers for electrochromic and photovoltaic applications. Upon completion of his Ph.D. in 2005, Barry moved to Prof. Jean Fréchet’s lab at UC Berkeley to further pursue his interests in polymer-based photovoltaics as an ACS-PRF Postdoctoral Fellow. After a three-year stay at Berkeley, Barry moved to the University of Southern California Department of Chemistry and Loker Hydrocarbon Research Institute as an Assistant Professor of Chemistry. Barry was promoted to Associate Professor with Tenure in 2015. Terje A. Skotheim is the founder of Lightsense and has a successful record in developing new technolo- gies and launching new products through several startups in fields as diverse as advanced lithium-sulfur batteries, MEMS devices, photovoltaic cells, and biosensors. His research interests have spanned across several disciplines in materials science, including conducting polymers, semiconductors, ion conduc- tors, and diamond-like carbon. He has held research positions and co-founded companies in Europe and the US, and was head of the conducting polymer group at DOE’s Brookhaven National Laboratory before launching his career as an entrepreneur. He received his B.S. in Physics from the Massachusetts Institute Technology and his Ph.D. in Physics from the University of California at Berkeley. vii Contributors Kazuo Akagi Shanshan Chen Research Organization of Science and Department of Energy Engineering Technology School of Energy and Chemical Engineering Ritsumeikan University Ulsan National Institute of Science and Kusatsu, Japan Technology (UNIST) Ulsan, South Korea Mats R. Andersson Flinders Institute for NanoScale Science and Xiankai Chen Technology School of Chemistry and Biochemistry and Flinders University Center for Organic Photonics and Adelaide, Australia Electronics Georgia Institute of Technology James H. Bannock Atlanta, Georgia Department of Chemistry Imperial College London Yoshiki Chujo London, United Kingdom Department of Polymer Chemistry Graduate School of Engineering, Kyoto J. Terence Blaskovits University Département de Chimie Kyoto, Japan Université Laval Québec City, Québec, Canada John C. de Mello Department of Chemistry Norwegian University Jean-Luc Bredas of Science and Technology (NTNU) School of Chemistry and Biochemistry and Trondheim, Norway Center for Organic Photonics and Electronics Georgia Institute of Technology Desta Gedefaw Atlanta, Georgia Flinders Institute for NanoScale Science and Technology Christopher M. Brown Flinders University Department of Chemistry Adelaide, Australia University of British Columbia and Vancouver, British Columbia, Canada School of Biological and Chemical Sciences Jeffrey Buenaflor Faculty of Science, Technology and Environment Department of Chemistry The University of South Pacific University of Washington Suva, Fiji Seattle, Washington ix x Contributors Karen K. Gleason Thomas Körzdörfer Department of Chemical Engineering Computational Chemistry Massachusetts Institute of Technology Institute of Chemistry Cambridge, Massachusetts University of Potsdam Potsdam, Germany Masayuki Gon Department of Polymer Chemistry Tanya Kumari Graduate School of Engineering, Kyoto Department of Energy Engineering University School of Energy and Chemical Engineering Kyoto, Japan Ulsan National Institute of Science and Technology (UNIST) Zhijie Guo Ulsan, South Korea Materials Research Institute and School of Biological and Chemical Sciences Emily L. Kynaston Queen Mary University of London Department of Chemistry London, United Kingdom University of Toronto Toronto, Ontario, Canada Martin J. Heeney Department of Chemistry Imperial College Mario Leclerc London Département de Chimie London, United Kingdom Université Laval Québec City, Québec, Canada Yun Huang Department of Chemistry Sang Myeon Lee University of Texas at San Antonio Department of Energy Engineering San Antonio, Texas School of Energy and Chemical Engineering Ulsan National Institute of Science and Shunichiro Ito Technology (UNIST) Department of Polymer Chemistry Ulsan, South Korea Graduate School of Engineering, Kyoto University Kyoto, Japan Hong Li School of Chemistry and Biochemistry Pradeepkumar Jagadesan and Center for Organic Photonics and Department of Chemistry Electronics University of Texas at San Antonio Georgia Institute of Technology San Antonio, Texas Atlanta, Georgia Malika Jeffries-EL Christine Luscombe Department of Chemistry Department of Materials Science and Boston University Engineering Boston, Massachusetts University of Washington Seattle, Washington So-Huei Kang Department of Energy Engineering Christian B. Nielsen School of Energy and Chemical Engineering Materials Research Institute and School of Ulsan National Institute of Science and Biological and Chemical Sciences Technology (UNIST) Queen Mary University of London Ulsan, South Korea London, United Kingdom Contributors xi Robert M. Pankow Dwight S. Seferos University of Southern California Department of Chemistry Department of Chemistry Department of Chemical Engineering and Los Angeles, California Applied Chemistry University of Toronto Toronto, Ontario, Canada Zachary S. Parr Materials Research Institute and School of Jessica Shaw Biological and Chemical Sciences Department of Chemistry Queen Mary University of London Boston University London, United Kingdom Boston, Massachusetts Seth C. Rasmussen Kazuo Tanaka Department of Chemistry and Biochemistry Department of Polymer Chemistry North Dakota State University Graduate School of Engineering, Kyoto Fargo, North Dakota University Kyoto, Japan Chad Risko Department of Chemistry and Center for Applied Tonghui Wang Energy Research (CAER) School of Chemistry and Biochemistry and University of Kentucky Center for Organic Photonics and Electronics Lexington, Kentucky Georgia Institute of Technology Atlanta, Georgia Sean M. Ryno Xiaoxue Wang School of Chemistry and Biochemistry and Department of Chemical Engineering Center for Organic Photonics and Electronics Massachusetts Institute of Technology Georgia Institute of Technology Cambridge, Massachusetts Atlanta, Georgia and Michael O. Wolf Department of Chemistry Department of Chemistry and Center for Applied University of British Columbia Energy Research (CAER) Vancouver, British Columbia, Canada University of Kentucky Lexington, Kentucky Changduk Yang Department of Energy Engineering Kirk S. Schanze School of Energy and Chemical Engineering Department of Chemistry Ulsan National Institute of Science and University of Texas at San Antonio Technology (UNIST) San Antonio, Texas Ulsan, South Korea Brian Schmatz Shuyang Ye University of Southern California Department of Chemistry Department of Chemistry University of Toronto Los Angeles, California Toronto, Ontario, Canada
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