Conjugated Polymers: Properties, Processing, and Applications

844 Pages·2019·42.948 MB·English

by  Reynolds J.R., Thompson B.C., Skotheim T.A. (ed.)

Conjugated Polymers
Properties, Processing, and Applications
Conjugated Polymers
Properties, Processing, and Applications
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.
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Contents
Preface to Fourth Edition .......................................................................................vii
Acknowledgments ....................................................................................................ix
Editors .......................................................................................................................xi
Contributors ...........................................................................................................xiii
1 Conjugated Polymer-Based OFET Devices........................................................1
Mark Nikolka and Henning Sirringhaus
2 Electrical Doping of Organic Semiconductors with Molecular Oxidants
and Reductants .................................................................................................21
Stephen Barlow, Seth R. Marder, Xin Lin, Fengyu Zhang, and Antoine Kahn
3 Electric Transport Properties in PEDOT Thin Films ....................................45
Nara Kim, Ioannis Petsagkourakis, Shangzhi Chen, Magnus Berggren, Xavier Crispin,
Magnus P. Jonsson, and Igor Zozoulenko
4 Thermoelectric Properties of Conjugated Polymers .....................................129
Kelly A. Peterson, Eunhee Lim, and Michael L. Chabinyc
5 Electrochemistry of Conducting Polymers ...................................................161
P. Audebert and F. Miomandre
6 Electrochromism in Conjugated Polymers – Strategies for Complete
and Straightforward Color Control ...............................................................201
Anna M. Ö sterholm, D. Eric Shen, and John R. Reynolds
7 Mechanical Properties of Semiconducting Polymers ..................................249
Mohammad A. Alkhadra, Andrew T. Kleinschmidt, Samuel E. Root, Daniel Rodriquez,
Adam D. Printz, Suchol Savagatrup, and Darren J. Lipomi
8 Magnetic Field Effects in Organic Semiconductors; Low and High
Fields, Steady State and Time Resolved ........................................................277
Eitan Ehrenfreund and Z. Valy Vardeny
9 Organic Electro-Optic Materials ..................................................................299
Larry Dalton
1 0 Establishing the Thermal Phase Behavior and its Influence on
Optoelectronic Properties of Semiconducting Polymers .............................329
Natalie Stingelin
v
vi Contents
11 Poly(3-alkylthiophenes): Controlled Manipulation of Microstructure
and its Impact on Charge Transport .............................................................351
Michael McBride, Guoyan Zhang, Martha Grover, and Elsa Reichmanis
1 2 Microstructural Characterization of Conjugated Organic
Semiconductors by X-Ray Scattering .............................................................391
Maged Abdelsamie and Michael F. Toney
13 Soft X-Ray Scattering Characterization of Polymer Semiconductors .........427
Long Ye, Samuel J. Stuard, and Harald Ade
1 4 Morphology Evolution and Interfacial Design of Conjugated Polymer-
Based Photovoltaics .......................................................................................459
Yao Liu and Thomas P. Russell
15 The Relevance of Solubility and Miscibility for the Performance of
Organic Solar Cells .......................................................................................485
Stefan Langner, Jose Dario Perea Ospina,
Chaohong Zhang, Ning Li, and Christoph J. Brabec
1 6 Processing-Structure-Function Relationships of Polymer-Acid-
Templated Conducting Polymers for Solid-State Devices ............................515
Melda Sezen-Edmonds and Yueh-Lin Loo
1 7 Conjugated Polymer Thin Films for Stretchable Electronics .......................535
Aristide Gumyusenge, William McNutt, and Jianguo Mei
1 8 Conducting Polymers for Electrochemical Capacitors .................................561
Luciano M. Santino, Yang Lu, Yifan Diao, Hongmin Wang, and Julio M. D’Arcy
1 9 Redox-Active Polymers as an Organic Energy Storage Material .................587
Kenichi Oyaizu and Hiroyuki Nishide
2 0 Electrochromics: Processing of Conjugated Polymers and Device
Fabrication on Semi-Rigid, Flexible, and Stretchable Substrates ................ 595
Matthew Baczkowski, Sneh Sinha, Mengfang Li, and Gregory Sotzing
2 1 Separation Techniques Using Conjugated Polymers ....................................629
Cheng-Wei Lin, Wai H. Mak, Brian T. McVerry, and Richard B. Kaner
2 2 Organic Bioelectronics Based on Mixed Ion–Electron Conductors ............679
Magnus Berggren, Erik O. Gabrielsson, Daniel T. Simon, and Klas Tybrandt
2 3 Conducting and Conjugated Polymers for Biosensing Applications ...........697
C. Pitsalidis, A.M. Pappa, C.M. Moysidou, D. Iandolo, and R.M. Owens
2 4 Conjugated Poly/ Oligo-Electrolytes for Cancer Diagnosis and Therapy .....743
Lingyun Zhou, Guillermo C. Bazan, and Shu Wang
2 5 Biomedical Applications of Organic Conducting Polymers ........................ 783
Alexander R. Harris, Paul J. Molino, Caiyun Wang,
Gordon G. Wallace, and Zhilian Yue
Index .......................................................................................................................813
Preface to Fourth Edition
Over 40 years has passed since the seminal polyacetylene doping experiments demonstrated that metal-
lic conductivity was possible in free-standing films of conjugated polymers. The field has developed
immensely in the interim, and this is fully captured in the now Fourth Edition of the Handbook of
Conducting Polymers, which follows the editions published in 1986, 1997, and 2007. What started out as
a field focused on, and known as, “Conducting Polymers,” has now broadened significantly to encom-
pass conjugated polymeric materials with a wide range of properties, including semi-conductivity, light
emission, bio-electronic effects, electrochemical redox activity, and a number of other properties in
addition to the original focus on charge transport.
With 41 chapters in the present Fourth Edition of the Handbook, we set the stage with three perspec-
tive chapters devoted to historical aspects, theoretical developments, and new conjugated polymer prep-
arations. One is struck with how new materials preparation through synthesis and processing continues
to serve as the backbone of the field, and with innovative processes being developed, such as chemical
vapor deposition, providing new avenues for both synthesis and applications. Researchers have made
enormous progress to develop a more complete picture of structure and morphology in these complex
systems using a myriad of characterization tools.
This has led to new capabilities in tuning optical, electronic, and redox properties optimized for par-
ticular effects. In conjunction with the success of PEDOT:PSS as a viable conducting polymer coating,
a range of applications are evolving towards commercial viability. These include field effect transistors,
solar cells, thermoelectrics, electrochromics, and charge storage. Particularly noteworthy are bio-elec-
tronic applications, which were alluded to in the Third Edition of the Handbook and now is blossoming
into multiple exciting fields of research. Building on the foundations laid over the years to understand
structure–property relationships, these tools are now employed to tailor interactions with biological
systems, one of the most exciting developments in the field. We expect to see the emergence of a range of
novel uses for functional conjugated polymeric systems in increasingly complex biological applications.
Examining the Handbook as a whole, and looking back at the history of the field over the last 40
years, there is no reason to expect the rate of development to slow down. New materials, new concepts,
and new applications are continuously being developed and reported. The field is dynamic and alive. It
is with great anticipation we wait to see what the next 10 years will bring.
John R. Reynolds
Atlanta, Georgia
Barry C. Thompson
Los Angeles, California
Terje A. Skotheim
Tucson, Arizona
vii
Acknowledgments
We appreciate and acknowledge the many contributions made by a large number of researchers and
authors who made this Fourth Edition of the Handbook of Conducting Polymers possible. We extend
our sincere thanks to them all, and a special thank you to the staff and editors at Taylor and Francis for
their effort and assistance in bringing this project to a successful conclusion. Again, and most impor-
tantly, this book is dedicated to our spouses, Ellen Skotheim and Dianne Reynolds, and now Emine
Boz-Thompson. We appreciate their understanding and support for this project, and the many other
projects we find ourselves involved in.
ix
Editors
Dr John R. Reynolds is a professor of chemistry and biochemistry, and materials science and engineer-
ing at the Georgia Institute of Technology with expertise in polymer chemistry. He serves as a member
of the Center for Organic Photonics and Electronics (COPE) and Director of the Georgia Tech Polymer
Network (GTPN). His research interests have involved electrically conducting and electroactive conju-
gated polymers for over 35 years with work focused to the development of new polymers by manipulat-
ing their fundamental organic structure in order to control their optoelectronic and redox properties.
His group has been heavily involved in developing new polyheterocycles for visible and infrared light
electrochromism, along with light emission from polymer and composite LEDs (both visible and near-
infrared) and light emitting electrochemical cells (LECs). Further work is directed to using organic
polymers and oligomers in charge storing supercapacitors and photovoltaic cells. Reynolds obtained
his MS (1982) and PhD (1984) degrees from the University of Massachusetts in polymer science and
engineering, he has published over 400 peer-reviewed scientific papers, has ~40 patents issued and ~15
patents pending, and serves as co-editor of the Handbook of Conducting Polymers. He was awarded the
ACS Applied Polymer Science Award in 2012 and is a Fellow of the Royal Society of Chemistry and the
Materials Research Society. He serves on the editorial board for the journals ACS Applied Materials
and Interfaces, ACS Central Science, Macromolecular Rapid Communications, Polymers for Advanced
Technologies, and the Journal of Macromolecular Science, Chemistry. John has been married since
October of 1986, has three children, and he and his wife make their home in Dunwoody, GA.
Dr Barry C. Thompson is an associate professor of chemistry and member of the Loker Hydrocarbon
Research Institute at the University of Southern California with expertise in polymer and organic chem-
istry. He received a BS in chemistry and physics from the University of Rio Grande in Rio Grande,
Ohio in 2000, a PhD in Chemistry from the University of Florida in 2005, and completed a postdoc at
UC Berkeley from 2005–2008. His research interests lie in the design and synthesis of conjugated and
electroactive polymers for a variety of applications including solar cells and batteries. A fundamental
interest in polymer synthesis is also reflected in extensive research on direct arylation polymerization
and the synthesis of non-conjugated electroactive polymers. Barry has more than 85 peer-reviewed sci-
entific publications. He has served on the editorial advisory boards for Macromolecules, ACS Macro
Letters, ACS Applied Materials and Interfaces, and Advanced Science. He lives in Rancho Palos Verdes,
CA with his wife and son.
Dr Terje A. Skotheim is the founder and chief executive of Lightsense Technology, Inc., a Tucson,
AZ-based technology company, the latest in a series of successful startups with Skotheim as a (co)
founder. Skotheim is an experienced developer of several technologies. His research interests over the
last 40 years span several disciplines in materials science, including electroactive and conjugated poly-
mers, molecular electronic materials, solid-state ion conductors, and nano-amorphous, and diamond-
like composites as new classes of electronic materials. Skotheim has pursued a wide range of applications
xi
xii Editors
of advanced materials including glucose sensors based on interactions between specially tailored elec-
troactive polymers and enzymes (licensed to a major glucose sensor manufacturer), a new class of ultra-
hard carbon-based wear-coatings (licensed to major automotive components company), pioneered the
development of the world’s first rechargeable Li-S battery (as founder of Sion Power), the application of
nano-amorphous composites as electrodes in OLED systems, the key inventor and developer of a new
class of infrared MEMS technology that is the platform for miniature IR sensors, and spectrometers
(foundation of two startups); and the application of IR MEMS-based systems to biomedical diagnostics
applications. Skotheim has held research positions in France, Sweden, Norway, and the United States
and was head of the conducting polymer program at Brookhaven National Laboratory before launch-
ing his career as an entrepreneur. Skotheim received his BS in physics from the Massachusetts Institute
of Technology and his PhD in physics from the University of California at Berkeley (1979). In addi-
tion to being the editor/co-editor of these volumes, he is the editor of Electroresponsive Molecular and
Polymeric Systems (Marcel Dekker), the author or more than 300 publications and 80 patents. Terje and
his wife of 46 years (the cover artist for this volume) divide their time between Tucson, AZ, and Palo
Alto, CA, where they tend to business, arts, and grandkids.