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ÊéÃûConjugated Polymers: A Practical Guide to Synthesis
×÷Õßby Klaus M¨¹llen, John R Reynolds, Toshio MasudaµÈ
Ò³Êý502
³ö°æÉç RSC Polymer Chemistry
Publication Date: October 18, 2013 | ISBN-10: 1849737991 | ISBN-13: 978-1849737999
Ŀ¼Chapter 1 Pi-Conjugated Polymers: The Importance of Polymer
Synthesis 1
John R. Reynolds
1.1 Historical Perspective 1
1.2 Considerations in Polymerizations 3
1.3 Side Chains, Processability and Molecular Weight 4
1.4 Structural Control via Repeat Unit and Functionality 5
1.5 Summary 9
Acknowledgements 10
References 10
Chapter 2 Polyacetylenes 12
Kazuo Akagi
2.1 Introduction 12
2.1.1 Polyacetylene (PA) 13
2.1.2 Helical Polyacetylene (H-PA) 18
2.1.3 H-PA with Bundle-Free Fibril Morphology 24
2.1.4 Morphology-Retaining Carbonization of
H-PA 28
2.2 Experimental Procedures 29
2.2.1 Synthesis of Shirakawa-Type PA 29
2.2.2 Synthesis of Naarmann and Theophilou-Type
PA 29
2.2.3 Synthesis of Tsukamoto-Type PA 30
2.2.4 Synthesis of High Mechanical Modulus and
Strength PA 30
2.2.5 Synthesis of Directly Aligned PA 31
RSC Polymer Chemistry Series No. 9
Conjugated Polymers: A Practical Guide to Synthesis
Edited by Klaus Mu¡§ llen, John R. Reynolds and Toshio Masuda
r The Royal Society of Chemistry 2014
Published by the Royal Society of Chemistry, www.rsc.org
xiii
.
Published on 18 October 2013 on http://pubs.rsc.org | doi:10.1039/9781849739771-FP013
2.2.6 Synthesis of Helical PA 32
2.2.7 Synthesis of Nematic Liquid Crystals and
Chiral Dopants 32
References 33
Chapter 3 Substituted Polyacetylenes 37
Fumio Sanda, Masashi Shiotsuki and Toshio Masuda
3.1 Introduction 37
3.1.1 Polymers of Aromatic Monosubstituted
Acetylenes 38
3.1.2 Polymers of Aliphatic Monosubstituted
Acetylenes 39
3.1.3 Polymers of Aromatic Disubstituted
Acetylenes 39
3.1.4 Polymers of Aliphatic Disubstituted
Acetylenes 40
3.1.5 Functions of Substituted Polyacetylenes 41
3.2 Experimental Procedures 42
3.2.1 Materials and General Polymerization
Procedures 42
3.2.2 Polymers of Aromatic Monosubstituted
Acetylenes 43
3.2.3 Polymers of Aliphatic Monosubstituted
Acetylenes 49
3.2.4 Polymers of Aromatic Disubstituted
Acetylenes 51
3.2.5 Polymers of Aliphatic Disubstituted
Acetylenes 54
3.2.6 Characterization and Remarks 56
References 58
Chapter 4 Polyphenylenes 61
Takakazu Yamamoto
4.1 Introduction 61
4.1.1 Polyphenylenes without Side Chain 62
4.1.2 Polyphenylenes with Side Chains or Side Rings 65
4.2 Experimental Procedures 66
4.2.1 Materials and General Polymerization
Procedures 66
4.2.2 Polyphenylenes without Side Chain 67
4.2.3 Polyphenylenes with Side Chains 71
4.2.4 Polyphenylenes with -N¼N- or -NR- Binding
Units 77
4.2.5 Polyphenylenes with Conjugated Side Rings 79
xiv Contents
.
Published on 18 October 2013 on http://pubs.rsc.org | doi:10.1039/9781849739771-FP013
View Online
4.2.6 Polyphenylenes with -SO3M or -NO2 Side
Chains Prepared via Ullmann Coupling 80
4.2.7 Characterization and Remarks 81
References 82
Chapter 5 Polyfluorenes 87
Byung Jun Jung, Hong-Ku Shim and Do-Hoon Hwang
5.1 Introduction 87
5.2 Experimental Procedures 88
5.2.1 Oxidative Polymerization 88
5.2.2 Yamamoto Coupling Polymerization 89
5.2.3 Suzuki Coupling Polymerization 92
5.3 Developments in Polymerization 99
5.3.1 Microwave-Assisted Polymerization 99
5.3.2 Other Synthetic Techniques 99
5.3.3 New Polymerization Methods 99
5.3.4 Purification of Polymers 100
5.4 Various Applications of Polyfluorenes 101
5.4.1 Polymer Light-Emitting Diodes (PLEDs) 101
5.4.2 Sensing Applications 105
5.4.3 Polymer Transistors and Solar Cells 105
5.4.4 Electron Injection Layers in Organic
Electronic Devices 107
5.5 Remarks 107
References 108
Chapter 6 Poly(carbazolylene)s 113
Sung Ju Cho and Andrew C. Grimsdale
6.1 Introduction 113
6.1.1 Poly(3,6-carbazolylene)s 114
6.1.2 Poly(1,8-carbazolylene)s 116
6.1.3 Poly(2,7-carbazolylene)s 116
6.1.4 Poly(3,9-carbazolylene)s 119
6.1.5 Ladder-Type Polycarbazolylenes 120
6.2 Experimental Procedures 121
6.2.1 Materials and General Procedures 121
6.2.2 Poly(3,6-carbazolylene)s 121
6.2.3 Poly(1,8-carbazolylene)s 123
6.2.4 Poly(2,7-carbazolylene)s 124
6.2.5 Poly(3,9-carbazolylene)s 128
6.2.6 Ladder-Type Poly(carbazolylene)s 129
References 132
Contents xv
.
Published on 18 October 2013 on http://pubs.rsc.org | doi:10.1039/9781849739771-FP013
View Online
Chapter 7 Poly(phenylenevinylene)s 134
Wallace W. H. Wong, Helga Seyler and Andrew B. Holmes
7.1 Introduction 134
7.2 Methods of Synthesis 135
7.2.1 Precursor Routes via Radical/Anionic
Polymerization Mechanism 135
7.2.2 Direct Routes to PPVs: Step-growth
Polycondensation 140
7.2.3 Ring-Opening Metathesis Polymerization 144
7.2.4 Alternative Routes 145
7.2.5 Comparison of Syntheses and Summary 146
7.3 Experimental Procedures 147
7.3.1 General Experimental Requirements 147
7.3.2 Example Procedures 148
References 151
Chapter 8 Poly(p-phenyleneethynylene)s and Poly(aryleneethynylene)s 156
Uwe H. F. Bunz
8.1 Introduction 156
8.1.1 Alkyl-PPEs and PAEs by Alkyne
Metathesis 159
8.1.2 Alkyl-PPEs by Pd Catalysis 161
8.1.3 Alkoxy-PPEs by Pd Catalysis 162
8.1.4 Poly(fluorenyleneethynylene)s by Alkyne
Metathesis 163
8.1.5 Other PAEs by Pd Catalysis 164
8.1.6 Side-Chain Functionalized PPEs by
Pd-Catalyzed Coupling 165
8.2 Experimental Procedures 165
8.2.1 Materials and General Polymerization
Procedures 165
8.2.2 Didodecyl-PPE 13b by Alkyne Metathesis
of 12b 168
8.2.3 Sonogashira Reactions, General
Remarks 168
8.2.4 Polyfluorenyleneethynylene by ADIMET 171
8.2.5 Quinoxaline-Containing PAEs 171
8.2.6 Benzothiadiazole-Containing PAE 173
8.2.7 Quinoline-Containing PAEs 173
8.2.8 Grafted PPEs 174
8.2.9 Characterization and Concluding
Remarks 176
References 177
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