Conjugated polymers and oligomers : structural and soft matter aspects

204 Pages·2018·39.029 MB·English

by  Knaapila, Matti

CONJUGATED POLYMERS
AND OLIGOMERS
Structural and Soft Matter Aspects
10591_9789813225756_TP.indd 1 23/11/17 4:23 PM
World Scientific Series in Materials and Energy
ISSN: 2335-6596
Series Editors:
Leonard C. Feldman (Rutgers University)
Jean-Luc Brédas (King Abdullah University of Science & Technology, Saudi Arabia)
Richard A. Haight (IBM Thomas J. Watson Research Ctr, USA)
Angus Alexander Rockett (University of Illinois at Urbana-Champaign, USA)
Eugene A. Fitzgerald (MIT, USA, Cornell, USA & The Innovation Interface, USA)
Gary Brudvig (Yale University, USA)
Michael R. Wasielewski (Northwestern University, USA)
Energy and sustainability are keywords driving current science and technology. Concerns about the
environment and the supply of fossil fuel have driven researchers to explore technological solutions
seeking alternative means of energy supply and storage. New materials and material structures are at
the very core of this research endeavor. The search for cleaner, cheaper, smaller and more efficient
energy technologies is intimately connected to the discovery and the development of new materials.
This collection focuses onmaterials-based solutions to the energy problem through a series of
case studies illustrating advances in energy-related materials research. The research studies employ
creativity, discovery, rationale design and improvement of the physical and chemical properties of
materials leading to new paradigms for competitive energy-production. The challenge tests both our
fundamental understanding of material and our ability to manipulate and reconfigure materials into
practical and useful configurations. Invariably these materials issues arise at the nano-scale!
For electricity generation, dramatic breakthroughs are taking place in the fields of solar cells and fuel
cells, the former giving rise to entirely new classes of semiconductors; the latter testing our knowledge
of the behavior of ionic transport through a solid medium. Inenergy-storage exciting developments are
emerging from the fields of rechargeable batteries and hydrogen storage. On the horizon are break-
throughs in thermoelectrics, high temperature superconductivity, and power generation. Still to emerge
are the harnessing of systems that mimic nature, ranging from fusion, as in the sun, to photosynthesis,
nature's photovoltaic. All of these approaches represent a body of materials–based research employing
the most sophisticated experimental and theoretical techniques dedicated to a commongoal. The aim of
this series is to capture these advances, through a collection of volumes authored by leading physicists,
chemists, biologists and engineers that represent the forefront of energy-related materials research.
Published
Vol. 9 Conjugated Polymers and Oligomers: Structural and Soft Matter Aspects
edited by Matti Knaapila (Technical University of Denmark, Denmark)
Vol. 8 Thin Films on Silicon: Electronic and Photonic Applications
edited by Vijay Narayanan (IBM Thomas J Watson Research Center, USA),
Martin M. Frank (IBM Thomas J Watson Research Center, USA) and
Alexander A. Demkov (The University of Texas at Austin, USA)
For further details, please visit: http://www.worldscientific.com/series/mae
(Continued at the end of the book)
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MATERIALS AND ENERGY – Vol.9
CONJUGATED POLYMERS
AND OLIGOMERS
Structural and Soft Matter Aspects
Editor
Matti Knaapila
Technical University of Denmark
World Scientific
NEW JERSEY • LONDON • SINGAPORE • BEIJING • SHANGHAI • HONG KONG • TAIPEI • CHENNAI • TOKYO
10591_9789813225756_TP.indd 2 23/11/17 4:23 PM
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Library of Congress Cataloging-in-Publication Data
Names: Knaapila, Matti, editor.
Title: Conjugated polymers and oligomers : structural and soft matter aspects / editor,
Matti Knaapila (Technical University of Denmark, Denmark).
Other titles: World Scientific series in materials and energy ; v. 9.
Description: Singapore ; Hackensack, NJ : World Scientific, [2017] |
Series: Materials and energy, ISSN 2335-6596 ; vol. 9
Identifiers: LCCN 2017030402| ISBN 9789813225756 (hardcover ; alk. paper) |
ISBN 9813225750 (hardcover ; alk. paper)
Subjects: LCSH: Conjugated polymers. | Oligomers.
Classification: LCC QD382.C66 C696 2017 | DDC 547/.70457--dc23
LC record available at https://lccn.loc.gov/2017030402
British Library Cataloguing-in-Publication Data
A catalogue record for this book is available from the British Library.
Copyright © 2018 by World Scientific Publishing Co. Pte. Ltd.
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Rhaimie - 10591 - Conjugated Polymers and Oligomers.indd 3 23-11-17 3:01:09 PM
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Preface
Soft materials are characterized by self-organized structures at mesoscopic
lengthscaleswellabovetheatomiclevel.Structuraltransformationstakeplace
atenergyscalescomparabletoroomtemperaturethermalenergies.Conjugated
polymers and oligomers have found widespread applications from OLEDs to
sensors. In addition to photophysics, charge transport and device fabrication,
this field has also been paralleled by phase behavioral studies since the first
structural reports of polythiophenes in the late 1980s by Winokur, Tashiro
and others which follows from even earlier work. This book identifies current
trendsofstructuralaspectsofconjugatedpolymersandoligomers.Allchapters
are written by leading scientists in their fields, ensuring state-of-art coverage.
Most properties of conjugated molecules and supramolecules stem from
theirstiffconjugatedbackbone.Theunderstandingofthisfundamentalstruc-
tural unit has become exceedingly advanced. This is described by Wunderlich,
MüllenandFytasinChapter1.Theareahasbenefittedgreatlyfromadvancesin
instrumentationsuchashighresolutiontransmissionelectronmicroscopyand
electrondiffractionandtomography.ThisisbeautifullydiscussedbyBrinkmann
in Chapter 2. Processing conjugated molecules from solutions has made
significantprogressandnowincludeswatersolutionsanddispersions.Strategies
tocontroltheirsolubilityinwaterincludeincorporationofhydrophilicterminal
groupsintosidechainsoffthepolymerbackboneaswellassurfactantsthatmay
formalayerbetweenthepolymerandwater.ThistopicisreviewedbyBurrows,
Stewart,RamosandJustinoinChapter3.Thishasledtoanincreasinglyactive
trendistousethemindetectingbiomoleculesandDNA.Thisrequirescareful
understanding of intermolecular interactions and the subsequent formation
of supramolecules. Interactions between conjugated molecules and DNA are
discussed by Alemán and Zanuy in Chapter 4. A comprehensive overview of
v
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vi ConjugatedPolymersandOligomers
the supramolecular assemblies of conjugated polymers and DNA is provided
by Knoops, Rubio-Magnieto, Richeter, Clément and Surin in Chapter 5.
The device performance depends on the microstructure and morphology of
conjugated materials and these on the other hand depend on the device
environmentitself.Thishasledscientiststofollowthedevicemanufacturingin
situbyfittingdeviceprocessingonsynchrotronbeamlines.Thistopicisfeatured
by Andreasen in Chapter 6. Current trends also embrace fundamental studies
not directly motivated by device prospects. These niches include for example
structural behavior of conjugated molecules under high pressure conditions,
discussed by Knaapila, Torkkeli, Scherf and Guha in Chapter 7.
This way each chapter recognizes an active research line where the soft
matterperspectivedominatestheresearchofconjugatedmaterials.Thethesisof
thewholebookistointroduceaspectrumofthemesfromfundamentalaspects
ofpersistentbackbonetowatersolubleconjugatedmoleculeswithsurfactants,
biomoleculesandDNA—andfromtheadvanceduseofsynchrotronradiation
and electron microscopy to the extreme conditions research. I feel that this
compact overview will be helpful and inspire and motivate scientists and
graduate students in their future work.
Ithanktheauthorsfortheireffortsandtherefereesforcarefullyreadingthe
chapters and giving comments that significantly improved the book. I thank
Prof. Michael J Winokur of the University of Wisconsin-Madison and Prof.
Jean-Luc Brédas of KAUST for the original idea and encouragement in the
editorial work.
Matti Knaapila
Department of Physics
Technical University of Denmark
Kgs. Lyngby, Denmark
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Contents
Preface v
Chapter 1: Shape Persistence in Polymers
and Supramolecular Assemblies 1
KatrinWunderlich,KlausMüllenandGeorgeFytas
Chapter 2: Structure in Thin Films of π-Conjugated
Semi-Conductors from the Perspective
of Transmission Electron Microscopy 29
MartinBrinkmann
Chapter 3: Structuring Conjugated Polymers
and Polyelectrolytes Through Self-Assembly 67
HughD.Burrows,BeverlyStewart,M.LuisaRamos
andLiciniaL.G.Justino
Chapter 4: Specific Interactions Between Electroactive
Conducting Polymers and DNA Bases 115
CarlosAlemánandDavidZanuy
Chapter 5: Supramolecular Assemblies of DNA/Conjugated
Polymers 139
JérémieKnoops,JeniferRubio-Magnieto,
SébastienRicheter,SébastienClément
andMathieuSurin
vii
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viii ConjugatedPolymersandOligomers
Chapter6: HighThroughputinsituScatteringofRoll-To-Roll
Coated Functional Polymer Films 159
JensWenzelAndreasen
Chapter 7: High Pressure Structural Studies of Conjugated
Molecules 175
MattiKnaapila,MikaTorkkeli,UllrichScherf
andSuchismitaGuha
Index 189
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Chapter 1
Shape Persistence in Polymers
and Supramolecular Assemblies
Katrin Wunderlich,∗ Klaus Müllen,∗,‡ George Fytas ∗,†,§
∗
MaxPlanckInstituteforPolymerResearch,
Ackermannweg10,55128Mainz,Germany
†DepartmentofMaterialsScience,
UniversityofCreteandIESL/FORTH,
71110Heraklion,Greece
‡[email protected]
§[email protected]
A thorough insight into the shape of polymers and supramolecular assemblies is of
crucial importance for the flow behavior, the packing in the solid as well as the
structureanddynamicsinnon-dilutesolutions.Inthischapter,wepresentthemain
experimental techniques that can reliably address persistence and compare different
polymers with reported persistence lengths ranging from few nanometers to few
hundredsnanometers.Specifically,wediscussnotonlytheso-calledrigid-rodpolymers
such as polyphenylenes, but also dendronized and helical polymers. These chain-
type macromolecules are generally considered as rigid or semi-rigid compared with
conventional homopolymers such as polyolefins. Next it is meaningful to compare
these covalently bonded polymers with supramolecular assemblies consisting of
amphiphilicpolymerssuchaspoly(ethyleneglycol)functionalizedbenzenederivatives
and poly(ethylene oxide-b-butadiene). Supramolecular assemblies can assume larger
rigiditythancovalentlybondedpolymers.Althoughwecanclassifydifferenttypesof
polymersandsupramolecularassembliesanddeterminetheirpersistencelengths,sofar,
thereisnoclearstructure-rigidityrelationship.Hence,apredictionofthepersistence
lengthssolelybasedonthemolecularstructuresremainsuncertain.
1