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ISSN 1000-6818CN 11-1892/O6CODEN WHXUEU
Acta Phys Chim Sin >> 2017,Vol.33>> Issue(12)>> 2550-2558     doi: 10.3866/PKU.WHXB201706071         中文摘要
Synthesis of Poly(bis-3,4-ethylenedioxythiophene methine)s with Side-Chain Comprising Electro-Optical Moieties and Alkyl Chain Effect in Solid State Polymerization
PEI Tong, PENG Kai, CAI Xin-Yi, YUAN Liang-Jie, XIA Jiang-Bin
College of Chemistry and Molecular Science, Wuhan University, Wuhan 430072, P. R. China
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New poly(bis-3,4-ethylenedioxythiophene methine)s derivatives with typical electro-optical moieties of thiophene, carbazole and fluorene as the side chains are obtained by facile solid state polymerization (SSP) or melt state polymerization (MSP). Detail characterizations of these polymers are carried out and some key monomers' crystals are obtained for structures analysis. It is found that existence of alkyl chains decrease monomers onset temperatures for SSP (Tonset) due to the weakening of the intermolecular interaction in crystals.



Keywords: Poly (bis-3,4-ethylenedioxythiophene methine) s derivatives   Solid and melt state polymerization   Alkyl chain effect  
Received: 2017-05-08 Accepted: 2017-06-06 Publication Date (Web): 2017-06-09
Corresponding Authors: XIA Jiang-Bin, YUAN Liang-Jie Email: jbxia@whu.edu.cn;ljyuan@whu.edu.cn

Fund: The project was supported by the National Natural Science Foundation of China (21371138), the Funds for Creative Research Groups of Hubei Province, China (2014CFA007) and the Fundamental Research Funds for the Central Universities, China (2042015kf0180).

Cite this article: PEI Tong, PENG Kai, CAI Xin-Yi, YUAN Liang-Jie, XIA Jiang-Bin. Synthesis of Poly(bis-3,4-ethylenedioxythiophene methine)s with Side-Chain Comprising Electro-Optical Moieties and Alkyl Chain Effect in Solid State Polymerization[J]. Acta Phys. -Chim. Sin., 2017,33 (12): 2550-2558.    doi: 10.3866/PKU.WHXB201706071

(1) Skotheim, T. A.; Elsenbaumer, R. L.; Reynolds, J. R. Hand Book of Conducting Polymers; Marcel Dekker Inc., New York, 1998.
(2) Hadziioannou, G.; Hutten, P. F. v. Semiconducting Polymers, 2nd ed.; Wiley-VCH; Weinheim, 2007.
(3) Meng, H.; Perepichka, D. F.; Bendikov, M.; Wudl, F.; Pan, G. Z;. Yu, W.; Dong, W.; Brown, S. J. Am. Chem. Soc. 2003, 125, 15151. doi: 10.1021/ja037115y
(4) Spencer, H. J.; Berridge, R.; Crouch, D. J.; Wright, S. P.; Giles, M. McCulloch, I.; Coles, S. J.; Hursthouse, M. B.; Skabara, P. J. J. Mater. Chem. 2003, 13, 2075. doi: 10.1039/B307575N
(5) Patra, A.; Wijsboom, Y. H.; Zade, S. S.; Li, M.; Sheynin, Y.; Leitus, G.; Bendikov, M. J. Am. Chem. Soc. 2008, 130, 6734. doi: 10.1021/ja8018675
(6) Lepeltier, M.; Hiltz, J.; Lockwood, T.; Bélanger-Gariépy, F.; Perepichka, D. F. J. Mater. Chem. 2009, 19, 5167. doi: 10.1039/B822997J
(7) Patra, A.; Wijsboom, Y. H.; Leitus, G.; Bendikov, M. Chem. Mater. 2011, 23, 896. doi: 10.1021/cm102395v
(8) Chen, S.; Xu, J.; Lu, B.; Duan, X.; Kong, F. Adv. Mater. Res. 2011, 239, 924. doi: 10.4028/www.scientific.net/AMR.239-242.924
(9) Gulprasertrat, N.; Chapromma, J.; Aree, T.; Sritana-anant, Y. J. Appl. Polym. Sci. 2015, 132, 42233/1. doi: 10.1002/app.42233
(10) Wagner, P.; Jolley, K. W.; Officer, D. L. Aust. J. Chem. 2011, 64, 335. doi: 10.1071/CH10413
(11) Yin, Y.; Li, Z.; Jin, J.; Tusy, C.; Xia, J. Synth. Met. 2013, 175, 97. doi: 10.1016/j.synthmet.2013.05.001
(12) Tusy, C.; Jiang, K.; Xia, J. Polym. Chem. 2015, 4, 1014. doi: 10.1039/C4PY01070A
(13) Koh, J. K.; Kim, J.; Kim, B.; Kim, J. H.; Kim, E. Adv. Mater. 2011, 23, 1641. doi: 10.1002/adma.201004715
(14) Chen, L.; Jin, J.; Shu, X.; Xia, J. J. Power Sources 2014, 248, 1234. doi: 10.1016/j.jpowsour.2013.09.139
(15) Yin, X.; Wu, F.; Fu, N.; Han, J.; Chen, D.; Xu, P.; He, M.; Lin, Y. ACS Appl. Mater. Inter. 2013, 5, 8423. doi: 10.1021/am401719e
(16) Papaspyrides, C. D.; Vouyiouka, S. N. Solid State Polymerization, John Wiley & Sons, Inc., 2009.
(17) Tusy, C.; Huang, L.; Jin, J.; Xia, J. RSC Adv. 2014, 4, 8011. doi: 10.1039/C3RA45014G
(18) Tusy, C.; Peng, K.; Huang, L.; Xia, J. RSC Adv. 2015, 5, 16292. doi: 10.1039/C4RA14915G
(19) Peng, K.; Pei, T.; Li, Z.; Huang, L.; Xia, J. RSC Adv. 2015, 5, 103841. doi: 10.1039/C5RA21122K
(20) Barres, A. L.; Allain, M.; Frere, P.; Batail, P. Isr. J. Chem. 2014, 54, 689. doi: 10.1002/ijch.201400068
(21) Jenekhe, S. A. Nature 1986, 322, 345. doi: 10.1038/322345a0
(22) Benincori, T.; Rizzo, S.; Sannicolo, F., Schiavon, G.; Zecchin, S.; Zotti, G. Macromolecules 2003, 36, 5114. doi: 10.1021/ma025919c
(23) Chen, W. C.; Liu, C. L.; Yen, C. T.; Tsai, F. C.; Tonzola, C. J.; Olson, N.; Jenekhe, S. A. Macromolecules 2004, 37, 5959. doi: 10.1021/ma049557f
(24) Zaman, M. B.; Perepichka, D. F. Chem. Commun. 2005, 4187. doi: 10.1039/B506138E
(25) Umeyama, T.; Watanabe, Y.; Oodoi, M.; Evgenia, D.; Shishido, T.; Imahori, H. J. Mater. Chem. 2012, 22, 24394. doi: 10.1039/C2JM33637E
(26) Ahn, S.; Yabumoto, K.; Jeong, Y.; Akagi, K. Polym. Chem. 2014, 5, 6977. doi: 10.1039/C4PY00849A
(27) Lemau de Talance, V.; Hissler, M.; Zhang, L-Z.; Karpati, T.; Nyulaszi, L.; Caras-Quintero, D.; Baeuerle, P.; Reau, R. Chem. Commun. 2008, 19, 2200. doi: 10.1039/B801335G
(28) Zheng, C.; Pu, S.; Xu, J.; Luo, M.; Huang, D.; Shen, L. Tetrahedron 2007, 63, 5437. doi: 10.1016/j.tet.2007.04.049
(29) Wang, H.; Chen, G.; Xu, X.; Chen, H.; Ji, S. Dye Pigm. 2010, 86, 238. doi: 10.1016/j.dyepig.2010.01.010
(30) Zhang, D.; Martín, V.; García-Moreno, I.; Costela, A.; Pérez-Ojeda, M. E.; Xiao, Y. Phys. Chem. Chem. Phys. 2011, 13, 13026. doi: 10.1039/C1CP21038F
(31) Hoffmann, K. J.; Knudsen, L.; Samuelsen, E. J.; Carlsen, P. H. J. Synth. Metal. 2000, 114, 161. doi: 10.1016/S0379-6779
(00)00244-7

(32) Sheldrick, G. M. SHELXTL, Version 6.14, Bruker Analytical X-ray Instruments, Inc, Madison, WI, USA, 2003.
(33) Sheldrick, G. M. Acta Crystallogr. Sect. A, 2008, 64, 112. doi: 10.1107/S0108767307043930
(34) Kvarnström, C.; Neugebauer, H.; Blomquist, S.; Ahonen, H. J.; Kankare, J.; Ivaska, A. Electrochim. Acta 1999, 44, 2739. doi: 10.1016/S0013-4686
(98)00405-8

(35) Louarn, G.; Kruszka, J.; Lefrant, S.; Zagorska, M.; Kulszewicz-Bayer, I.; Pron, A. Synth. Met. 1993, 61, 233. doi: 10.1016/0379-6779
(93)91267-6

(36) Agashe, M. S.; Jose, C. I. J. Chem. Soc. Faraday Trans. 2 1977, 73, 1232. doi: 10.1039/F29797500733
(37) Paul, A.; Gigueère, I.; Liu, D. J. Chem. Phy. 1952, 20, 136. doi: 10.1063/1.1700155
(38) Xia, Y.; MacDiarmid, A. G.; Epstein, A. J. Macromolecules 1994, 27, 7212. doi: 10.1021/ma00102a033
(39) Hohnholz, D.; MacDiarmid, A. G.; Sarno, D. M.; Jones, J. W. E. Chem. Commun. 2001, 2444. doi: 10.1039/B107130K
(40) Benincori, T.; Rizzo, S.; Sannicoloò, F.; Schiavon, G.; Zecchin, S.; Zotti, G. Macromolecules 2003, 36, 5114. doi: 10.1021/ma025919c
(41) Chen, W. C.; Liu, C. L.; Yen, C. T.; Tsai, F. C.; Tonzola, C. J.; Olson, N.; Jenekhe, S. A. Macromolecules 2004, 37, 5959. doi: 10.1021/ma049557f
(42) Itoh, T.; Tachino, K.; Akira, N.; Uno, T.; Kubo, M.; Tohnai, N.; Miyata, M. Macromolecules 2015, 48, 2935. doi: 10.1021/ma502606s
(43) Williams, J. O. Annu. Rep. Prog. Chem., Sect. C: Phys. Chem. 1980, 77, 63. doi: 10.1039/PC9807700063
(44) Lauher, J. W.; Fowler, F. W.; Goroff, N. S. Acc. Chem. Res. 2008, 41, 1215. doi: 10.1021/ar8001427

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