臺灣博碩士論文加值系統

本研究成功合成主鏈上具有含氮雜環benzo[c]cinnoline之共軛高分子，包含poly(1,3,4-oxadiazole)s (POXD (I) 與 (T))、 poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene]s (MEH-PPVs) (P10、P25與P50)以及 polyfluorenes (BF10、BF25與BF50)，並進一步對此些高分子進行表徵。其中，透過對含氮雜環benzo[c]cinnoline之四級胺化，高分子BF50形成多電解質(polyelectrolyte) BF50Br。在poly(1,3,4-oxadiazole)s之研究中，透過循環伏安法(cyclic voltammetry)的量測，POXD (I) 與 (T)發現到兩段的還原峰型。將循環伏安法之結果搭配分子模擬，我們推論出第一段之還原應是oxadiazole單元接受了第一個電子，第二段還原則是benzo[c]cinnoline單元接受了第二個電子。此結果顯示出oxadiazole相對於benzo[c]cinnoline，具有較佳之電子親和力。而MEH-PPV之衍生物P10、P25與 P50被做為半導體層，導入構型為下閘極-上接觸(bottom-gate, top-contact)之有機場效電晶體(organic field-effect transistors, OFETs)，並在空氣環境中進行元件之量測。其中，高分子P10量測到p型材料之特性，即傳導電洞之性質。相對來說，P25與 P50則無法量測到電洞之傳導，但卻展現出n型材料傳導電子之特性。同時，將P50為半導體層之有機場效電晶體在空氣環境下進行30天的保存，其電子傳導率(electron mobility)並沒有顯著之下降，數值仍維持在同一個階乘，展現出良好之穩定性。據我們所知，此研究首先提出具有良好空氣穩定性以及n型材料特性之MEH-PPV衍生物，並證明透過benzo[c]cinnoline單元之導入，可將p型材料MEH-PPV轉換成n型之材料。具有benzo[c]cinnoline單元之polyfluorenes (BF10, BF25, and BF50)則被配置成稀薄溶液，並以352 nm之紫外光(UV)進行照射。照光後可觀察到溶液的光致發光(photoluminescence, PL)強度提升。此現象之原因應為照光後，高分子主鏈上的fluorene單元形成含有氧原子之基團，導致高分子之有效共軛鏈段變短，同時抑制了高分子之施體(donor)與受體(acceptor)間的交互作用力。如將照光後之溶液加入三氟醋酸(trifluoroacetic acid)，則可進一步抑制其溶液之光致發光。此研究最後，透過建立紫外光劑量(UV dose)與光致發光量子效率(PL quantum yields)之線性關係，顯示出此系列材料有應用於感測紫外光強度之潛力。新型之多電解質BF50Br在高極性溶劑DMSO、NMP、甲醇(methanol)與 乙醇(ethanol)中，展現出比BF50更好的溶解度，並在這些溶劑中發出藍光。其中，以NMP作為溶劑之BF50Br溶液，展現出比前驅物BF50更高的的光致發光量子效率以及更純的藍光。透過一系列對於含有benzo[c]cinnoline單元之共軛高分子之研究，顯示出具有benzo[c]cinnoline單元之共軛高分子，皆具有獨特之光電特性。

The conjugated polymers, including poly(1,3,4-oxadiazole)s (POXD (I) and (T)), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene]s (MEH-PPVs) (P10, P25, and P50), and polyfluorenes (BF10, BF25, and BF50) containing benzo[c]cinnoline moieties, were synthesized and characterized. The polyfluorene containing benzo[c]cinnoline moieties, BF50, was further quaternized to obtain the polyelectrolyte, BF50Br. Two reduction peaks were observed for POXD (I) and (T) during cyclic voltammetry (CV) cathodic scan. From CV characterization combined with the results from molecular simulation, we concluded that the first reduction occurred at oxadiazole moiety and benzo[c]cinnoline moiety was responsible for the second reduction. It indicates that oxadiazole has stronger electron affinity than benzo[c]cinnoline. The bottom-gate, top-contact organic field-effect transistors (OFETs) based on P10, P25, and P50 were performed under ambient conditions. The OFET based on P10 only exhibited p-channel characteristic. In contrast, we could not determine the hole mobilities of P25 and P50. The OFETs of these two polymers only exhibited n-channel characteristics. No significant variation in electron mobility can be observed after P50-based OFET was stored under ambient conditions up to 30 days. To the best of our knowledge, this is the first time that air-stable n-channel MEH-PPV derivatives have ever been reported. It indicated that p-type MEH-PPV can be transformed into n-type materials upon incorporation of benzo[c]cinnoline moieties. By UV irradiation (352 nm), the PL (photoluminescence) intensity of dilute polymer solutions of BF10, BF25, and BF50 was enhanced. The PL emission enhancement was attributed to the shorter conjugated length and the reduced donor-acceptor interaction caused by oxygen-containing groups that were formed on fluorene moieties by UV irradiation. The enhanced emission could be quenched further by the addition of proton donors such as trifluoroacetic acid. The completely alternating polymer BF50 consisting of fluorene and benzo[c]cinnoline moieties in dilute THF solution showed linear relationship between UV doses and PL quantum yields after UV irradiation. It exhibited good potential for UV-sensing applications. The solubility of the polyelectrolyte, BF50Br, in polar solvents including DMSO, NMP, methanol, and ethanol was improved obviously after modification. BF50Br exhibited blue-light emitting at 437 nm in NMP, accompanied with higher quantum yield and narrower FWHM (full width at half maximum) than its precursor polymer. The blue-light emission of BF50Br was also observed in DMSO, methanol, and ethanol. The unique optoelectronic properties have been investigated in a series of researches of various polymers containing benzo[c]cinnoline moieties.

摘要 I
Abstract III
Acknowledge V
Contents VIII
List of Tables XII
List of Schemes XIII
List of Figures XIV
Preface 1
Chapter A: Introduction and Motivation 2
Introduction 3
Organic Conjugated Polymers 3
Electron-Donors 7
Electron-Acceptors 12
Donor-Acceptor Copolymers Containing Dual Acceptors 18
2-Dimensional Donor-Acceptor Copolymers 20
High-Performance Donor-Acceptor Copolymers 23
Benzo[c]cinnoline 26
Motivation 28
Chapter B: Experimental 29
Materials 30
Measurements 31
Synthesis of monomers and polymers 33
4,4’-Dibromo-2,2’-dinitrobiphenyl (1) 33
3,8-Dibromobenzo[c]cinnoline (2) 34
3,8-Dicyanobenzo[c]cinnoline (3) 34
3,8-Benzo[c]cinnolinedicarboxylic acid (4) 35
3,8-Benzo[c]cinnolinedicarbaldehyde (5) 36
Polyhydrazide and Polyoxadiazole Derivatives Containing Benzo[c]cinnoline Moieties (PHA (I), PHA (T), POXD (I), and POXD (T)) 37
MEH-PPV Derivatives Containing Benzo[c]cinnoline Moieties (P10, P25, and P50) 39
Polyfluorene Derivatives Containing Benzo[c]cinnoline Moieties (PFO, BF10, BF25, and BF50) and Model Compound (FBF) 41
Polyelectrolyte Containing Benzo[c]cinnoline Derivative, 2,3-Dihydrobenzo[c]pyrazolo[1,2-a]cinnolium Cation Moieties (BF50Br) 44
Fabrication of devices 45
Electron-Only Devices 45
Organic Field-Effect Transistors 45
Simulation methods 47
PHA (T) and POXD (T) 47
MEH-PPV and P50 47
Chapter C: Investigations on the Electrochemical Properties of New Conjugated Polymers Containing Benzo[c]cinnoline and Oxadiazole Moieties 49
Abstract 50
Introduction 51
RESULTS AND DISCUSSION 54
Physical Properties of PHA (I), PHA (T), POXD (I), and POXD (T) 54
Electrochemical Properties 56
Conclusions 64
Chapter D: Synthesis and Properties of Air-Stable n-Channel Semiconductors Based on MEH-PPV Derivatives Containing Benzo[c]cinnoline Moieties 65
Abstract 66
Introduction 67
Results and Discussion 71
Synthesis of Monomer 71
Synthesis of Polymers 73
Optical Properties 78
Electrochemical Properties 89
Organic Field-Effect Transistor Performance 94
Conclusions 99
Chapter E: UV-Irradiation-Enhanced Photoluminescence Emission of Polyfluorenes Containing Heterocyclic Benzo[c]cinnoline Moieties 100
Abstract 101
Introduction 102
Results and Discussion 105
Synthesis and Characterization 105
Electrochemical Properties 111
Optical Properties 114
UV-Irradiation-Enhanced PL Emission 118
Conclusions 136
Chapter F: Novel Polyelectrolyte Containing Benzo[c]cinnoline Derivative, 2,3-Dihydrobenzo[c]pyrazolo[1,2-a]cinnolium Cation Moieties 137
Abstract 138
Introduction 139
Results and Discussion 142
Synthesis and Characterization 142
Electrochemical Properties 147
Optical Properties 149
Conclusions 156
Chapter G: Conclusions 157
Conclusions 158
Chapter H: References 160
References 161

1.M.-C. Choi, Y. Kim and C.-S. Ha, Progress in Polymer Science, 2008, 33, 581-630.
2.Q.-D. Ling, D.-J. Liaw, C. Zhu, D. S.-H. Chan, E.-T. Kang and K.-G. Neoh, Progress in Polymer Science, 2008, 33, 917-978.
3.Y.-J. Cheng, S.-H. Yang and C.-S. Hsu, Chemical Reviews, 2009, 109, 5868-5923.
4.C. L. Chochos and S. A. Choulis, in Progress in Polymer Science, 2011, vol. 36, pp. 1326-1414.
5.C.-L. Liu, C.-H. Lin, C.-C. Kuo, S.-T. Lin and W.-C. Chen, Progress in Polymer Science, 2011, 36, 603-637.
6.L.-H. Xie, C.-R. Yin, W.-Y. Lai, Q.-L. Fan and W. Huang, Progress in Polymer Science, 2012, 37, 1192-1264.
7.C. Wang, H. Dong, W. Hu, Y. Liu and D. Zhu, Chemical Reviews, 2011, 112, 2208-2267.
8.A. Yassar, L. Miozzo, R. Gironda and G. Horowitz, Progress in Polymer Science, 2013, 38, 791-844.
9.X. Guo, M. Baumgarten and K. Müllen, Progress in Polymer Science, 2013, 38, 1832-1908.
10.A. J. Heeger, Chemical Society Reviews, 2010, 39, 2354-2371.
11.H. Sirringhaus, P. J. Brown, R. H. Friend, M. M. Nielsen, K. Bechgaard, B. M. W. Langeveld-Voss, A. J. H. Spiering, R. A. J. Janssen, E. W. Meijer, P. Herwig and D. M. de Leeuw, Nature, 1999, 401, 685-688.
12.J.-F. Chang, B. Sun, D. W. Breiby, M. M. Nielsen, T. I. Sölling, M. Giles, I. McCulloch and H. Sirringhaus, Chemistry of Materials, 2004, 16, 4772-4776.
13.G. Zhao, Y. He and Y. Li, Advanced Materials, 2010, 22, 4355-4358.
14.Y. Liang and L. Yu, Polymer Reviews, 2010, 50, 454-473.
15.N. S. Sariciftci, L. Smilowitz, A. J. Heeger and F. Wudl, Science, 1992, 258, 1474-1476.
16.G. Gustafsson, Y. Cao, G. M. Treacy, F. Klavetter, N. Colaneri and A. J. Heeger, Nature, 1992, 357, 477-479.
17.H. A. M. van Mullekom, J. A. J. M. Vekemans, E. E. Havinga and E. W. Meijer, Materials Science and Engineering: R: Reports, 2001, 32, 1-40.
18.A. P. Kulkarni, C. J. Tonzola, A. Babel and S. A. Jenekhe, Chemistry of Materials, 2004, 16, 4556-4573.
19.S.-C. Lo and P. L. Burn, Chemical Reviews, 2007, 107, 1097-1116.
20.T. Kashiki, S. Shinamura, M. Kohara, E. Miyazaki, K. Takimiya, M. Ikeda and H. Kuwabara, Organic Letters, 2009, 11, 2473-2475.
21.T. Kashiki, M. Kohara, I. Osaka, E. Miyazaki and K. Takimiya, The Journal of Organic Chemistry, 2011, 76, 4061-4070.
22.C. B. Nielsen, B. C. Schroeder, A. Hadipour, B. P. Rand, S. E. Watkins and I. McCulloch, Journal of Materials Chemistry, 2011, 21, 17642-17645.
23.I. McCulloch, R. S. Ashraf, L. Biniek, H. Bronstein, C. Combe, J. E. Donaghey, D. I. James, C. B. Nielsen, B. C. Schroeder and W. Zhang, Accounts of Chemical Research, 2012, 45, 714-722.
24.X. Zhao, D. Yang, H. Lv, L. Yin and X. Yang, Polymer Chemistry, 2013, 4, 57-60.
25.S.-C. Lan, P.-A. Yang, M.-J. Zhu, C.-M. Yu, J.-M. Jiang and K.-H. Wei, Polymer Chemistry, 2013, 4, 1132-1140.
26.X. Guo, S. Wang, V. Enkelmann, M. Baumgarten and K. Müllen, Organic Letters, 2011, 13, 6062-6065.
27.J. Peet, J. Y. Kim, N. E. Coates, W. L. Ma, D. Moses, A. J. Heeger and G. C. Bazan, Nat Mater, 2007, 6, 497-500.
28.J. K. Lee, W. L. Ma, C. J. Brabec, J. Yuen, J. S. Moon, J. Y. Kim, K. Lee, G. C. Bazan and A. J. Heeger, Journal of the American Chemical Society, 2008, 130, 3619-3623.
29.S. Wang, M. Kappl, I. Liebewirth, M. Müller, K. Kirchhoff, W. Pisula and K. Müllen, Advanced Materials, 2012, 24, 417-420.
30.W. Zhang, J. Smith, S. E. Watkins, R. Gysel, M. McGehee, A. Salleo, J. Kirkpatrick, S. Ashraf, T. Anthopoulos, M. Heeney and I. McCulloch, Journal of the American Chemical Society, 2010, 132, 11437-11439.
31.H. Bronstein, D. S. Leem, R. Hamilton, P. Woebkenberg, S. King, W. Zhang, R. S. Ashraf, M. Heeney, T. D. Anthopoulos, J. d. Mello and I. McCulloch, Macromolecules, 2011, 44, 6649-6652.
32.M. Zhang, X. Guo, X. Wang, H. Wang and Y. Li, Chemistry of Materials, 2011, 23, 4264-4270.
33.Y. Zhang, J. Zou, H.-L. Yip, K.-S. Chen, D. F. Zeigler, Y. Sun and A. K. Y. Jen, Chemistry of Materials, 2011, 23, 2289-2291.
34.Y. Zhang, J. Zou, H. L. Yip, K. S. Chen, J. A. Davies, Y. Sun and A. K. Y. Jen, Macromolecules, 2011, 44, 4752-4758.
35.X. Guo, M. Zhang, J. Tan, S. Zhang, L. Huo, W. Hu, Y. Li and J. Hou, Advanced Materials, 2012, 24, 6536-6541.
36.C.-Y. Chang, Y.-J. Cheng, S.-H. Hung, J.-S. Wu, W.-S. Kao, C.-H. Lee and C.-S. Hsu, Advanced Materials, 2012, 24, 549-553.
37.Y.-L. Chen, C.-Y. Chang, Y.-J. Cheng and C.-S. Hsu, Chemistry of Materials, 2012, 24, 3964-3971.
38.Y.-X. Xu, C.-C. Chueh, H.-L. Yip, F.-Z. Ding, Y.-X. Li, C.-Z. Li, X. Li, W.-C. Chen and A. K. Y. Jen, Advanced Materials, 2012, 24, 6356-6361.
39.H. Yan, Z. Chen, Y. Zheng, C. Newman, J. R. Quinn, F. Dotz, M. Kastler and A. Facchetti, Nature, 2009, 457, 679-686.
40.Z. Chen, Y. Zheng, H. Yan and A. Facchetti, Journal of the American Chemical Society, 2009, 131, 8-9.
41.E. Zhou, J. Cong, Q. Wei, K. Tajima, C. Yang and K. Hashimoto, Angewandte Chemie International Edition, 2011, 50, 2799-2803.
42.H. Chen, Y. Guo, G. Yu, Y. Zhao, J. Zhang, D. Gao, H. Liu and Y. Liu, Advanced Materials, 2012, 24, 4618-4622.
43.I. Kang, T. K. An, J.-a. Hong, H.-J. Yun, R. Kim, D. S. Chung, C. E. Park, Y.-H. Kim and S.-K. Kwon, Advanced Materials, 2013, 25, 524-528.
44.C. Kanimozhi, N. Yaacobi-Gross, K. W. Chou, A. Amassian, T. D. Anthopoulos and S. Patil, Journal of the American Chemical Society, 2012, 134, 16532-16535.
45.J. Lee, A. R. Han, J. Kim, Y. Kim, J. H. Oh and C. Yang, Journal of the American Chemical Society, 2012, 134, 20713-20721.
46.R. Stalder, J. Mei, J. Subbiah, C. Grand, L. A. Estrada, F. So and J. R. Reynolds, Macromolecules, 2011, 44, 6303-6310.
47.T. Lei, Y. Cao, Y. Fan, C.-J. Liu, S.-C. Yuan and J. Pei, Journal of the American Chemical Society, 2011, 133, 6099-6101.
48.T. Lei, J.-H. Dou and J. Pei, Advanced Materials, 2012, 24, 6457-6461.
49.J. Mei, D. H. Kim, A. L. Ayzner, M. F. Toney and Z. Bao, Journal of the American Chemical Society, 2011, 133, 20130-20133.
50.T. Lei, J.-H. Dou, Z.-J. Ma, C.-H. Yao, C.-J. Liu, J.-Y. Wang and J. Pei, Journal of the American Chemical Society, 2012, 134, 20025-20028.
51.G. W. P. Van Pruissen, F. Gholamrezaie, M. M. Wienk and R. A. J. Janssen, Journal of Materials Chemistry, 2012, 22, 20387-20393.
52.Y. Koizumi, M. Ide, A. Saeki, C. Vijayakumar, B. Balan, M. Kawamoto and S. Seki, Polymer Chemistry, 2013, 4, 484-494.
53.P. Sonar, S. P. Singh, Y. Li, M. S. Soh and A. Dodabalapur, Advanced Materials, 2010, 22, 5409-5413.
54.S. Cho, J. Lee, M. Tong, J. H. Seo and C. Yang, Advanced Functional Materials, 2011, 21, 1910-1916.
55.A. J. Kronemeijer, E. Gili, M. Shahid, J. Rivnay, A. Salleo, M. Heeney and H. Sirringhaus, Advanced Materials, 2012, 24, 1558-1565.
56.J. D. Yuen, J. Fan, J. Seifter, B. Lim, R. Hufschmid, A. J. Heeger and F. Wudl, Journal of the American Chemical Society, 2011, 133, 20799-20807.
57.F. Huang, K.-S. Chen, H.-L. Yip, S. K. Hau, O. Acton, Y. Zhang, J. Luo and A. K. Y. Jen, Journal of the American Chemical Society, 2009, 131, 13886-13887.
58.C. Duan, W. Cai, F. Huang, J. Zhang, M. Wang, T. Yang, C. Zhong, X. Gong and Y. Cao, Macromolecules, 2010, 43, 5262-5268.
59.S.-L. Hsu, C.-M. Chen and K.-H. Wei, Journal of Polymer Science Part A: Polymer Chemistry, 2010, 48, 5126-5134.
60.C. Duan, K.-S. Chen, F. Huang, H.-L. Yip, S. Liu, J. Zhang, A. K. Y. Jen and Y. Cao, Chemistry of Materials, 2010, 22, 6444-6452.
61.L. Huo, J. Hou, S. Zhang, H.-Y. Chen and Y. Yang, Angewandte Chemie International Edition, 2010, 49, 1500-1503.
62.Q. Peng, X. Liu, D. Su, G. Fu, J. Xu and L. Dai, Advanced Materials, 2011, 23, 4554-4558.
63.M. Wang, X. Hu, P. Liu, W. Li, X. Gong, F. Huang and Y. Cao, Journal of the American Chemical Society, 2011, 133, 9638-9641.
64.L. Huo, S. Zhang, X. Guo, F. Xu, Y. Li and J. Hou, Angewandte Chemie International Edition, 2011, 50, 9697-9702.
65.Y. Huang, X. Guo, F. Liu, L. Huo, Y. Chen, T. P. Russell, C. C. Han, Y. Li and J. Hou, Advanced Materials, 2012, 24, 3383-3389.
66.L. Dou, J. Gao, E. Richard, J. You, C.-C. Chen, K. C. Cha, Y. He, G. Li and Y. Yang, Journal of the American Chemical Society, 2012, 134, 10071-10079.
67.C. Luo, A. K. K. Kyaw, L. A. Perez, S. Patel, M. Wang, B. Grimm, G. C. Bazan, E. J. Kramer and A. J. Heeger, Nano Letters, 2014, 14, 2764-2771.
68.B. Nketia-Yawson, H.-S. Lee, D. Seo, Y. Yoon, W.-T. Park, K. Kwak, H. J. Son, B. Kim and Y.-Y. Noh, Advanced Materials, 2015, 27, 3045-3052.
69.H.-J. Yun, S.-J. Kang, Y. Xu, S. O. Kim, Y.-H. Kim, Y.-Y. Noh and S.-K. Kwon, Advanced Materials, 2014, 26, 7300-7307.
70.G. Kim, S.-J. Kang, G. K. Dutta, Y.-K. Han, T. J. Shin, Y.-Y. Noh and C. Yang, Journal of the American Chemical Society, 2014, 136, 9477-9483.
71.H.-R. Tseng, H. Phan, C. Luo, M. Wang, L. A. Perez, S. N. Patel, L. Ying, E. J. Kramer, T.-Q. Nguyen, G. C. Bazan and A. J. Heeger, Advanced Materials, 2014, 26, 2993-2998.
72.L. Huo, T. Liu, X. Sun, Y. Cai, A. J. Heeger and Y. Sun, Advanced Materials, 2015, 27, 2938-2944.
73.J. You, L. Dou, K. Yoshimura, T. Kato, K. Ohya, T. Moriarty, K. Emery, C.-C. Chen, J. Gao, G. Li and Y. Yang, Nature Communications, 2013, 4, 1446.
74.Y. Liu, J. Zhao, Z. Li, C. Mu, W. Ma, H. Hu, K. Jiang, H. Lin, H. Ade and H. Yan, Nature Communications, 2014, 5.
75.S.-H. Liao, H.-J. Jhuo, P.-N. Yeh, Y.-S. Cheng, Y.-L. Li, Y.-H. Lee, S. Sharma and S.-A. Chen, Scientific Reports, 2014, 4, 6813.
76.A. R. b. M. Yusoff, D. Kim, H. P. Kim, F. K. Shneider, W. J. da Silva and J. Jang, Energy & Environmental Science, 2015, 8, 303-316.
77.J. You, C.-C. Chen, Z. Hong, K. Yoshimura, K. Ohya, R. Xu, S. Ye, J. Gao, G. Li and Y. Yang, Advanced Materials, 2013, 25, 3973-3978.
78.Z. Zheng, S. Zhang, M. Zhang, K. Zhao, L. Ye, Y. Chen, B. Yang and J. Hou, Advanced Materials, 2015, 27, 1189-1194.
79.H. Zhou, Y. Zhang, C.-K. Mai, S. D. Collins, G. C. Bazan, T.-Q. Nguyen and A. J. Heeger, Advanced Materials, 2015, 27, 1767-1773.
80.X. Shao, X. Luo, X. Hu and K. Wu, Journal of Physical Chemistry B, 2006, 110, 15393-15402.
81.Y. Yu, A. R. Sadique, J. M. Smith, T. R. Dugan, R. E. Cowley, W. W. Brennessel, C. J. Flaschenriem, E. Bill, T. R. Cundari and P. L. Holland, Journal of the American Chemical Society, 2008, 130, 6624-6638.
82.P.-Y. Orain, J.-F. Capon, F. Gloaguen, P. Schollhammer and J. Talarmin, International Journal of Hydrogen Energy, 2010, 35, 10797-10802.
83.N. J. Leonard, Chemical Reviews, 1945, 37, 269-286.
84.O. V. Vinogradova and I. A. Balova, Chemistry of Heterocyclic Compounds, 2008, 1-22.
85.J. Waluk, A. Grabowska and B. Pakulstroka, Journal of Luminescence, 1980, 21, 277-291.
86.C. T. Lin and J. A. Stikeleather, Chemical Physics Letters, 1976, 38, 561-566.
87.H. Inoue, Y. Hiroshima and K. i. Tomiyama, Bulletin of the Chemical Society of Japan, 1981, 54, 2209-2210.
88.M. J. Sienkowska, J. M. Farrar, F. Zhang, S. Kusuma, P. A. Heiney and P. Kaszynski, Journal of Materials Chemistry, 2007, 17, 1399-1411.
89.B. K. Choi and T. Yamamoto, Electrochemistry Communications, 2003, 5, 566-570.
90.L. Huo, C. He, M. Han, E. Zhou and Y. Li, Journal of Polymer Science Part A: Polymer Chemistry, 2007, 45, 3861-3871.
91.M. Kubo, C. Takimoto, Y. Minami, T. Uno, T. Itoh and M. Shoyama, Macromolecules, 2005, 38, 7314-7320.
92.M. Ranger, D. Rondeau and M. Leclerc, Macromolecules, 1997, 30, 7686-7691.
93.R. G. R. Bacon and S. G. Pande, Journal of the Chemical Society C: Organic, 1970, 1967-1973.
94.D. A. Patrick, D. W. Boykin, W. D. Wilson, F. A. Tanious, J. Spychala, B. C. Bender, J. E. Hall, C. C. Dykstra, K. A. Ohemeng and R. R. Tidwell, European Journal of Medicinal Chemistry, 1997, 32, 781-793.
95.C. P. Joshua and V. N. R. Pillai, Tetrahedron, 1974, 30, 3333-3337.
96.L. Akcelrud, Progress in Polymer Science, 2003, 28, 875-962.
97.C.-F. Shu, R. Dodda, F.-I. Wu, M. S. Liu and A. K. Y. Jen, Macromolecules, 2003, 36, 6698-6703.
98.C.-Y. Chuang, P.-I. Shih, C.-H. Chien, F.-I. Wu and C.-F. Shu, Macromolecules, 2007, 40, 247-252.
99.S. Beaupré, P.-L. T. Boudreault and M. Leclerc, Advanced Materials, 2010, 22, E6-E27.
100.P. Herguth, X. Jiang, M. S. Liu and A. K. Y. Jen, Macromolecules, 2002, 35, 6094-6100.
101.N. Blouin, A. Michaud, D. Gendron, S. Wakim, E. Blair, R. Neagu-Plesu, M. Belletête, G. Durocher, Y. Tao and M. Leclerc, Journal of the American Chemical Society, 2008, 130, 732-742.
102.R. Qin, W. Li, C. Li, C. Du, C. Veit, H.-F. Schleiermacher, M. Andersson, Z. Bo, Z. Liu, O. Inganäs, U. Wuerfel and F. Zhang, Journal of the American Chemical Society, 2009, 131, 14612-14613.
103.L. H. Slooff, S. C. Veenstra, J. M. Kroon, D. J. D. Moet, J. Sweelssen and M. M. Koetse, Applied Physics Letters, 2007, 90, 143506.
104.M. D. Curtis, Macromolecules, 2001, 34, 7905-7910.
105.Y. Yang, Q. Pei and A. J. Heeger, Synthetic Metals, 1996, 78, 263-267.
106.M. Berggren, O. Inganas, G. Gustafsson, J. Rasmusson, M. R. Andersson, T. Hjertberg and O. Wennerstrom, Nature, 1994, 372, 444-446.
107.Q. Pei and Yang, Journal of the American Chemical Society, 1996, 118, 7416-7417.
108.G. Yu, J. Gao, J. C. Hummelen, F. Wudl and A. J. Heeger, Science, 1995, 270, 1789-1791.
109.M. Strukelj, F. Papadimitrakopoulos, T. M. Miller and L. J. Rothberg, Science, 1995, 267, 1969-1972.
110.C. J. Tonzola, M. M. Alam and S. A. Jenekhe, Advanced Materials, 2002, 14, 1086-1090.
111.L. J. Lindgren, F. Zhang, M. Andersson, S. Barrau, S. Hellström, W. Mammo, E. Perzon, O. Inganäs and M. R. Andersson, Chemistry of Materials, 2009, 21, 3491-3502.
112.F. Zhang, W. Mammo, L. M. Andersson, S. Admassie, M. R. Andersson and O. Inganäs, Advanced Materials, 2006, 18, 2169-2173.
113.F. Zhang, J. Bijleveld, E. Perzon, K. Tvingstedt, S. Barrau, O. Inganas and M. R. Andersson, Journal of Materials Chemistry, 2008, 18, 5468-5474.
114.S. P. Liu, H. S. O. Chan and N. G. Siu-Choon, Journal of Polymer Science, Part A: Polymer Chemistry, 2004, 42, 4792-4801.
115.B. C. Thompson, Y. G. Kim, T. D. McCarley and J. R. Reynolds, Journal of the American Chemical Society, 2006, 128, 12714-12725.
116.J. A. Mikroyannidis, K. M. Gibbons, A. P. Kulkarni and S. A. Jenekhe, Macromolecules, 2008, 41, 663-674.
117.J.-C. Chen, C.-J. Chiang and Y.-C. Liu, Synthetic Metals, 2010, 160, 1953-1961.
118.C. Adachi, T. Tsutsui and S. Saito, Applied Physics Letters, 1990, 56, 799-801.
119.H. Meng, W.-L. Yu and W. Huang, Macromolecules, 1999, 32, 8841-8847.
120.Y.-Z. Lee, X. Chen, S.-A. Chen, P.-K. Wei and W.-S. Fann, Journal of the American Chemical Society, 2001, 123, 2296-2307.
121.S.-W. Hwang and Y. Chen, Macromolecules, 2002, 35, 5438-5443.
122.J. C. Chen, H. C. Wu, C. J. Chiang, L. C. Peng, T. Chen, L. Xing and S. W. Liu, Polymer, 2011, 52, 6011-6019.
123.T. Yasuda, T. Imase and T. Yamamoto, Macromolecules, 2005, 38, 7378-7385.
124.Y. Li, Y. Cao, J. Gao, D. Wang, G. Yu and A. J. Heeger, Synthetic Metals, 1999, 99, 243-248.
125.P. Destruel, P. Jolinat, R. Clergereaux and J. Farenc, Journal of Applied Physics, 1999, 85, 397-400.
126.J. Pommerehne, H. Vestweber, W. Guss, R. F. Mahrt, H. Bässler, M. Porsch and J. Daub, Advanced Materials, 1995, 7, 551-554.
127.M.-Y. Hwang, M.-Y. Hua and S.-A. Chen, Polymer, 1999, 40, 3233-3235.
128.T. Yamamoto, K. Sugiyama, T. Kushida, T. Inoue and T. Kanbara, Journal of the American Chemical Society, 1996, 118, 3930-3937.
129.C.-C. Lee, M.-Y. Chang, P.-T. Huang, Y. C. Chen, Y. Chang and S.-W. Liu, Journal of Applied Physics, 2007, 101, 114501.
130.C. R. Newman, C. D. Frisbie, D. A. Da Silva Filho, J. L. Brédas, P. C. Ewbank and K. R. Mann, Chemistry of Materials, 2004, 16, 4436-4451.
131.J. Zaumseil and H. Sirringhaus, Chemical Reviews, 2007, 107, 1296-1323.
132.A. R. Murphy and J. M. J. Fréchet, Chemical Reviews, 2007, 107, 1066-1096.
133.A. Facchetti, Materials Today, 2007, 10, 28-37.
134.Y. Wen and Y. Liu, Advanced Materials, 2010, 22, 1331-1345.
135.J. E. Anthony, A. Facchetti, M. Heeney, S. R. Marder and X. Zhan, Advanced Materials, 2010, 22, 3876-3892.
136.X. Zhao and X. Zhan, Chemical Society Reviews, 2011, 40, 3728-3743.
137.H. Usta, A. Facchetti and T. J. Marks, Accounts of Chemical Research, 2011, 44, 501-510.
138.A. Tsumura, H. Koezuka and T. Ando, Applied Physics Letters, 1986, 49, 1210-1212.
139.H. N. Tsao, D. M. Cho, I. Park, M. R. Hansen, A. Mavrinskiy, D. Y. Yoon, R. Graf, W. Pisula, H. W. Spiess and K. Müllen, Journal of the American Chemical Society, 2011, 133, 2605-2612.
140.J. S. Ha, K. H. Kim and D. H. Choi, Journal of the American Chemical Society, 2011, 133, 10364-10367.
141.J. Lee, A. R. Han, J. Kim, Y. Kim, J. H. Oh and C. Yang, Journal of the American Chemical Society, 2012, 134, 20713-20721.
142.M. Sommer, Journal of Materials Chemistry C, 2014, 2, 3088-3098.
143.J. A. Mikroyannidis, I. K. Spiliopoulos, T. S. Kasimis, A. P. Kulkarni and S. A. Jenekhe, Journal of Polymer Science, Part A: Polymer Chemistry, 2004, 42, 2112-2123.
144.P. Karastatiris, J. A. Mikroyannidis, I. K. Spiliopoulos, A. P. Kulkarni and S. A. Jenekhe, Macromolecules, 2004, 37, 7867-7878.
145.B. C. Thompson, L. G. Madrigal, M. R. Pinto, T. S. Kang, K. S. Schanze and J. R. Reynolds, Journal of Polymer Science, Part A: Polymer Chemistry, 2005, 43, 1417-1431.
146.W. F. Su, K. M. Yeh and Y. Chen, Journal of Polymer Science, Part A: Polymer Chemistry, 2007, 45, 4377-4388.
147.L. Huo, Z. Tan, X. Wang, Y. Zhou, M. Han and Y. Li, Journal of Polymer Science, Part A: Polymer Chemistry, 2008, 46, 4038-4049.
148.P. Karastatiris, J. A. Mikroyannidis and I. K. Spiliopoulos, Journal of Polymer Science, Part A: Polymer Chemistry, 2008, 46, 2367-2378.
149.Y. Zhang, B. de Boer and P. W. M. Blom, Physical Review B, 2010, 81, 085201.
150.A. R. Inigo, C. H. Tan, W. Fann, Y. S. Huang, G. Y. Perng and S. A. Chen, Advanced Materials, 2001, 13, 504-508.
151.M. Muratsubaki, Y. Furukawa, T. Noguchi, T. Ohnishi, E. Fujiwara and H. Tada, Chemistry Letters, 2004, 33, 1480-1481.
152.W. W. Zhu, S. Xiao and I. Shih, Applied Surface Science, 2004, 221, 358-363.
153.Y. R. Liu, J. B. Peng and P. T. Lai, Applied Surface Science, 2007, 253, 6987-6991.
154.S.-i. Watanabe, H. Tanaka, S.-i. Kuroda, A. Toda, H. Tomikawa, S. Nagano and T. Seki, Applied Physics Express, 2012, 5, 021602.
155.L.-L. Chua, J. Zaumseil, J.-F. Chang, E. C.-W. Ou, P. K.-H. Ho, H. Sirringhaus and R. H. Friend, Nature, 2005, 434, 194-199.
156.H. Lee, D. Vak, K. J. Baeg, Y. C. Nah, D. Y. Kim and Y. Y. Noh, Journal of Nanoscience and Nanotechnology, 2013, 13, 3321-3330.
157.C. A. Amorim, M. R. Cavallari, G. Santos, F. J. Fonseca, A. M. Andrade and S. Mergulhão, Journal of Non-Crystalline Solids, 2012, 358, 484-491.
158.G. Padmanaban and S. Ramakrishnan, Journal of the American Chemical Society, 2000, 122, 2244-2251.
159.P. J. Lynch, L. O'Neill, D. Bradley, H. J. Byrne and M. McNamara, Macromolecules, 2007, 40, 7895-7901.
160.Y. Jin, J. Y. Kim, S. Song, Y. Xia, J. Kim, H. Y. Woo, K. Lee and H. Suh, Polymer, 2008, 49, 467-473.
161.S.-H. Chen and Y. Chen, Macromolecules, 2004, 38, 53-60.
162.E. Wang, M. Wang, L. Wang, C. Duan, J. Zhang, W. Cai, C. He, H. Wu and Y. Cao, Macromolecules, 2009, 42, 4410-4415.
163.E. Wang, L. Hou, Z. Wang, S. Hellström, F. Zhang, O. Inganäs and M. R. Andersson, Advanced Materials, 2010, 22, 5240-5244.
164.H. Zhou, L. Yang, S. C. Price, K. J. Knight and W. You, Angewandte Chemie International Edition, 2010, 49, 7992-7995.
165.X. Guo, H. Xin, F. S. Kim, A. D. T. Liyanage, S. A. Jenekhe and M. D. Watson, Macromolecules, 2010, 44, 269-277.
166.F. B. Dias, S. Pollock, G. Hedley, L. O. Pålsson, A. Monkman, I. I. Perepichka, I. F. Perepichka, M. Tavasli and M. R. Bryce, Journal of Physical Chemistry B, 2006, 110, 19329-19339.
167.Q. Hou, Q. Zhou, Y. Zhang, W. Yang, R. Yang and Y. Cao, Macromolecules, 2004, 37, 6299-6305.
168.L. Zhang, S. Hu, J. Chen, Z. Chen, H. Wu, J. Peng and Y. Cao, Advanced Functional Materials, 2011, 21, 3760-3769.
169.J. Wakita, S. Inoue, N. Kawanishi and S. Ando, Macromolecules, 2010, 43, 3594-3605.
170.C. Reichardt, Chemical Reviews, 1994, 94, 2319-2358.
171.S. A. Jenekhe, L. Lu and M. M. Alam, Macromolecules, 2001, 34, 7315-7324.
172.Q. Fang and T. Yamamoto, Macromolecules, 2004, 37, 5894-5899.
173.J. Du, Q. Fang, X. Chen, S. Ren, A. Cao and B. Xu, Polymer, 2005, 46, 11927-11933.
174.J. Natera, L. Otero, L. Sereno, F. Fungo, N.-S. Wang, Y.-M. Tsai, T.-Y. Hwu and K.-T. Wong, Macromolecules, 2007, 40, 4456-4463.
175.Q. Fang, B. Xu, B. Jiang, H. Fu, X. Chen and A. Cao, Chemical Communications, 2005, 1468-1470.
176.W.-C. Wu, C.-L. Liu and W.-C. Chen, Polymer, 2006, 47, 527-538.
177.G.-S. Liou, N.-K. Huang and Y.-L. Yang, Journal of Polymer Science Part A: Polymer Chemistry, 2007, 45, 48-58.
178.H. W. Chang, K. H. Lin, C. C. Chueh, G. S. Liou and W. C. Chen, Journal of Polymer Science, Part A: Polymer Chemistry, 2009, 47, 4037-4050.
179.Y.-C. Kung, W.-F. Lee, S.-H. Hsiao and G.-S. Liou, Journal of Polymer Science Part A: Polymer Chemistry, 2011, 49, 2210-2221.
180.J. R. Lakowicz, Principles of Fluorescence Spectroscopy, 2006, Springer, Singapore, 3rd edn, 2006.
181.K. L. Gering, L. L. Lee, L. H. Landis and J. L. Savidge, Fluid Phase Equilibria, 1989, 48, 111-139.
182.M. S. Altuwaim, K. H. A. E. Alkhaldi, A. S. Al-Jimaz and A. A. Mohammad, Journal of Chemical Thermodynamics, 2012, 48, 39-47.
183.G. Zhang, H. Xu, K. Liu, Y. Li, L. Yang and M. Yang, Synthetic Metals, 2010, 160, 1945-1952.
184.S. Zhang, Y. Wen, W. Zhou, Y. Guo, L. Ma, X. Zhao, Z. Zhao, S. Barlow, S. R. Marder, Y. Liu and X. Zhan, Journal of Polymer Science, Part A: Polymer Chemistry, 2013, 51, 1550-1558.
185.X. Zhao, Y. Wen, L. Ren, L. Ma, Y. Liu and X. Zhan, Journal of Polymer Science Part A: Polymer Chemistry, 2012, 50, 4266-4271.
186.Y. Yang, Q. Zhao, W. Feng and F. Li, Chemical Reviews, 2013, 113, 192-270.
187.S. W. Thomas, G. D. Joly and T. M. Swager, Chemical Reviews, 2007, 107, 1339-1386.
188.H. N. Kim, Z. Guo, W. Zhu, J. Yoon and H. Tian, Chemical Society Reviews, 2011, 40, 79-93.
189.J. Wu, W. Liu, J. Ge, H. Zhang and P. Wang, Chemical Society Reviews, 2011, 40, 3483-3495.
190.S. Holdcroft, Macromolecules, 1991, 24, 4834-4838.
191.B. H. Cumpston and K. F. Jensen, Synthetic Metals, 1995, 73, 195-199.
192.M. Yan, L. J. Rothberg, F. Papadimitrakopoulos, M. E. Galvin and T. M. Miller, Physical Review Letters, 1994, 73, 744-747.
193.N. Ljungqvist and T. Hjertberg, Macromolecules, 1995, 28, 5993-5999.
194.A. T. H. Koch, N. T. Harrison, N. Haylett, R. Daik, W. J. Feast and R. H. Friend, Synthetic Metals, 1999, 100, 113-122.
195.D. M. Johansson, G. Srdanov, G. Yu, M. Theander, O. Inganäs and M. R. Andersson, Macromolecules, 2000, 33, 2525-2529.
196.V. N. Bliznyuk, S. A. Carter, J. C. Scott, G. Klärner, R. D. Miller and D. C. Miller, Macromolecules, 1999, 32, 361-369.
197.E. J. W. List, R. Guentner, P. Scanducci de Freitas and U. Scherf, Advanced Materials, 2002, 14, 374-378.
198.L. Romaner, A. Pogantsch, P. Scandiucci de Freitas, U. Scherf, M. Gaal, E. Zojer and E. J. W. List, Advanced Functional Materials, 2003, 13, 597-601.
199.A. P. Kulkarni, X. Kong and S. A. Jenekhe, The Journal of Physical Chemistry B, 2004, 108, 8689-8701.
200.T. V. Duncan and S.-J. Park, The Journal of Physical Chemistry B, 2009, 113, 13216-13221.
201.E. L. Dane, S. B. King and T. M. Swager, Journal of the American Chemical Society, 2010, 132, 7758-7768.
202.M. H. M. Cativo, A. C. Kamps, J. Gao, J. K. Grey, G. R. Hutchison and S. J. Park, Journal of Physical Chemistry B, 2013, 117, 4528-4535.
203.N. Miyaura and A. Suzuki, Chemical Reviews, 1995, 95, 2457-2483.
204.J.-C. Chen, H.-C. Wu, C.-J. Chiang, T. Chen and L. Xing, Journal of Materials Chemistry C, 2014, 2, 4835-4846.
205.T. A. Koizumi, S. Kato and T. Yamamoto, Journal of Polymer Science, Part A: Polymer Chemistry, 2011, 49, 4204-4212.
206.A. P. Kulkarni, Y. Zhu and S. A. Jenekhe, Macromolecules, 2005, 38, 1553-1563.
207.A. P. Kulkarni, X. Kong and S. A. Jenekhe, Macromolecules, 2006, 39, 8699-8711.
208.J.-L. Brédas, J. Cornil and A. J. Heeger, Advanced Materials, 1996, 8, 447-452.
209.B. Liu, W.-L. Yu, J. Pei, S.-Y. Liu, Y.-H. Lai and W. Huang, Macromolecules, 2001, 34, 7932-7940.
210.Y. Zhu, K. M. Gibbons, A. P. Kulkarni and S. A. Jenekhe, Macromolecules, 2007, 40, 804-813.
211.N. S. Bayliss and E. G. McRae, The Journal of Physical Chemistry, 1954, 58, 1002-1006.
212.D. M. Hercules and L. B. Rogers, The Journal of Physical Chemistry, 1960, 64, 397-400.
213.H. Baba and C. Mugiya, Bulletin of the Chemical Society of Japan, 1970, 43, 13-19.
214.K. T. Kamtekar, H. L. Vaughan, B. P. Lyons, A. P. Monkman, S. U. Pandya and M. R. Bryce, Macromolecules, 2010, 43, 4481-4488.
215.W. Schnabel, Polymers and Light, WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007.
216.A. G. Anastassiou, H. S. Kasmai and M. R. Saadein, Helvetica Chimica Acta, 1981, 64, 617-619.
217.H. T. Nagasawa and H. R. Gutmann, Journal of Medicinal Chemistry, 1966, 9, 719-725.
218.J. Malthête, J. Canceill, J. Gabard and J. Jacques, Tetrahedron, 1981, 37, 2823-2828.
219.R. D. Scurlock, B. Wang, P. R. Ogilby, J. R. Sheats and R. L. Clough, Journal of the American Chemical Society, 1995, 117, 10194-10202.
220.M. S. A. Abdou, F. P. Orfino, Y. Son and S. Holdcroft, Journal of the American Chemical Society, 1997, 119, 4518-4524.
221.G. Kwak, M. Fujiki, T. Sakaguchi and T. Masuda, Macromolecules, 2005, 39, 319-323.
222.W.-E. Lee, H. Park and G. Kwak, Chemical Communications, 2011, 47, 659-661.
223.F. Uckert, Y. H. Tak, K. Müllen and H. Bässler, Advanced Materials, 2000, 12, 905-908.
224.T. Yasuda and T. Yamamoto, Macromolecules, 2003, 36, 7513-7519.
225.A. Balamurugan, M. L. P. Reddy and M. Jayakannan, Journal of Polymer Science Part A: Polymer Chemistry, 2009, 47, 5144-5157.
226.W.-J. Li, B. Liu, Y. Qian, L.-H. Xie, J. Wang, S.-B. Li and W. Huang, Polymer Chemistry, 2013, 4, 1796-1802.
227.W. Ngampeungpis, G. Tumcharern, P. Pienpinijtham and M. Sukwattanasinitt, Dyes and Pigments, 2014, 101, 103-108.
228.C. V. Hoven, A. Garcia, G. C. Bazan and T.-Q. Nguyen, Advanced Materials, 2008, 20, 3793-3810.
229.H. Jiang, P. Taranekar, J. R. Reynolds and K. S. Schanze, Angewandte Chemie International Edition, 2009, 48, 4300-4316.
230.F. Huang, H. Wu and Y. Cao, Chemical Society Reviews, 2010, 39, 2500-2521.
231.D. Mecerreyes, Progress in Polymer Science, 2011, 36, 1629-1648.
232.W. Jaeger, J. Bohrisch and A. Laschewsky, Progress in Polymer Science, 2010, 35, 511-577.
233.L. Ying, P. Zalar, S. D. Collins, Z. Chen, A. A. Mikhailovsky, T.-Q. Nguyen and G. C. Bazan, Advanced Materials, 2012, 24, 6496-6501.
234.Z. B. Henson, Y. Zhang, T.-Q. Nguyen, J. H. Seo and G. C. Bazan, Journal of the American Chemical Society, 2013, 135, 4163-4166.
235.S. Prescher, S. Ghasimi, P. Höhne, K. Grygiel, K. Landfester, K. A. I. Zhang and J. Yuan, Macromolecular Rapid Communications, 2014, 35, 1925-1930.
236.F. Huang, L. Hou, H. Shen, J. Jiang, F. Wang, H. Zhen and Y. Cao, Journal of Materials Chemistry, 2005, 15, 2499-2507.
237.R. Kang, S.-H. Oh and D.-Y. Kim, ACS Applied Materials & Interfaces, 2014, 6, 6227-6236.
238.D. G. Farnum, R. J. Alaimo and J. M. Dunston, Journal of Organic Chemistry, 1967, 32, 1130-1134.
239.H. Fischer, F. A. Neugebauer, H. Chandra and M. C. R. Symons, Journal of the Chemical Society, Perkin Transactions 2, 1989, 727-730.
240.J. W. Barton, Advances in Heterocyclic Chemistry. Academic Press, 1979, 24, 151-185.
241.G. Jang, J. Kim, D. Kim and T. S. Lee, Polymer Chemistry, 2015, 6, 714-720.
242.H.-C. Wu, J.-C. Chen and H.-Z. Lin, Macromolecules, 2015, 48, 4373-4381.