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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 xvi 9781849737999_p0_v1_s260x420.JPG QQͼƬ20140504120726.jpg |
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