Influence of Alkyl Spacer on Electrosynthesis of Polyacrylate Functionalized Polycarbazole Network Films

Abstract

Abstract: Two novel acrylate functionalized monomers N-[10-(acryloxy)decyl]carbazole(MACZ10) and N-[12-(acryloxy)dodecyl]carbazole(MACZ12), which incorporate a carbazole moiety at the terminal of the hydrocarbon chain, were designed and synthesized. Through radical polymerization of MACZs led to the formation of two precursor polymers, poly(N-[10-(acryloxy)decyl]carbazole)(PMACZ10) and poly{N-[12-(acryloxy)dodecyl]carbazole}(PMACZ12). The results of GPC indicate that molecular weight of polymer decreased with the growth of alkyl chain, fluorescence spectral show that the emission peak at 353 nm of the polymer decreased with the growth of alkyl chain. Free-standing and conducting conjugated polycarbazole network poly-{poly(N-[10-(acryloxy)decyl]carbazole)}(PPMACZ10) and poly-{poly(N-[12-(acryloxy)dodecyl]carbazole)}(PPMACZ12) films were synthesized electrochemically by direct anodic oxidation of PMACZ10 and PMACZ12 in THF containing additional 10%(volume fraction) boron trifluoride diethyl etherate(BFEE). PPMACZs films obtained from this medium show good electrochemical behavior and good thermal stability. As-formed PPMACZs films were characterized by UV-Vis, infrared, fluorescence spectroscopy and thermal analysis. Fluorescence spectral studies revealed that PPMACZs films were good blue light emitters.

Key words: Polycarbazole, Conducting polymer, Polyacrylate, Alkyl spacer, Network film

TrendMD:

ZHU Zhao-Jin, LU Bao-Yang, LIU Cong-Cong, WANG Lu-Yan*, XU Jing-Kun*, PEI Mei-Shan. Influence of Alkyl Spacer on Electrosynthesis of Polyacrylate Functionalized Polycarbazole Network Films[J]. Chem. J. Chinese Universities, 2010, 31(10): 2102.

References

[1]ZHANG Zhi-Pan(张志攀), SHI Gao-Quan(石高全), WU Xu-Feng(吴旭峰), QU Liang-Ti(曲良体). Acta. Polym. Sin.(高分子学报)[J], 2004, (1): 140—144 [2]Roncali J.. Chem. Rev.[J], 1992, 92: 711—738 [3]Xu J. K., Shi G. Q., Qu L. T., Zhang J.. Synth. Met.[J], 2003, 221: 135—136 [4]Sadki S., Schottland P., Brodie N., Sabouraud G.. Chem. Soc. Rev.[J], 2000, 29: 283—293 [5]Ouyang J. Y., Li Y. F.. Polymer[J], 1997, 38: 1971—1976 [6]Ouyang J. Y., Li Y. F.. Polymer[J], 1997, 38: 3997—3999 [7]Qin H., Wan M., Matthew B., Dai L.. Macromolecules[J], 2001, 4: 675—677 [8]Xu J. K., Nie G. M., Zhang S. S., Han X. J., Hou J., Pu S. Z.. J. Polym. Sci. Polym. Chem.[J], 2005, 43: 1444—1453 [9]Yurtsever M., Yurtsever E.. Polymer[J], 2002, 43: 6019—6025 [10]Xu Jian, Zhan Yi-qiang, Hou Xiao-yuan, Xiao Fei. Chinese Journal of Chemistry[J], 2005, 23(4): 454—458 [11]YING Lei(应磊), CHEN Zhao(陈钊), JIANG Jia-Xing(蒋加兴), GUAN Rong(管榕), YANG Wei(杨伟), CAO Yong(曹镛). Chem. J. Chinese Universities(高等学校化学学报)[J], 2009, 30(2): 403—407 [12]WANG Guang-Rong(王光荣), ZENG He-Ping(曾和平). Chem. J. Chinese Universities(高等学校化学学报)[J], 2009, 30(6): 1140—1145 [13]BO Dong-Sheng(薄冬生), REN Ai-Min(任爱民), FENG Ji-Kang(封继康), YANG Li(杨丽). Chem. J. Chinese Universities(高等学校化学学报)[J], 2007, 28(5): 955—959 [14]Obrien R. N., Santhanam K. S. V.. Electrochim. Acta[J], 1989, 34: 493—498 [15]Levesque I., Bertrand P. O., Blouin N., Leclerc M., Zecchin S., Zotti G., Ratcliffe C. I., Klug D. D., Gao X., Gao F. M., Tse J. S.. Chem.Mat.[J], 2007, 19: 2128—2138 [16]Diamant Y., Chen J., Han H., Kamenev B., Tsybeskov L., Grebel H.. Synth. Met.[J], 2005, 151: 202—207 [17]Miao Hua-Ming, Zhang Hong-Lin, Xu Jing-Kun, Fan Chang-Li, Dong Bin, Zeng Li-Qiang, Zhao Feng. Chin. J. Chem.[J], 2008, 26(10): 1922—1928 [18]Wei Zhen-hong, Xu Jing-kun, Nie Guang-ming, Du Yu-kou, Pu Shou-zhi. J. Electroanal. Chem.[J], 2006, 589: 112 [19]SHEN Yan-Yan(申艳艳), MIAO Hua-Ming(苗华明), ZHANG Hong-Lin(张洪林), XU Jing-Kun(徐景坤), LU Bao-Yang(卢宝阳). Acta. Polym. Sin[J]. 2008, (11): 1089 [20]Ravindranath R., Ajikumar P. K., Bahulayan S., Hanafiah N. B. M., Baba A., Advincula R. C., Knoll W., Valiyaveettil S.. J. Phys. Chem. B[J], 2007, 111: 6336—6343 [21]Barik S., Valiyaveettil S.. Macromolecules[J], 2008, 41(17): 6376—6386 [22]Huang C. Y., Jiang G. Q., Advincula R.. Macromolecules[J], 2008, 41: 4661—4670 [23]Fulghum T. M., Taranekar P., Advincula R. C.. Macromolecules[J], 2008, 41: 5681—5687 [24]Xu J. K., Zhou W. Q., Peng H. P., Pu S. Z., Wang J. W., Yan L. S.. Polym. J.[J], 2006, 38: 369—375 [25]Topchiev A. V., Zavgorodnii S. V., Paushkin Y. M.. Boron Fluoride and Its Compounds as Catalysts in Organic Chemistry[M], New York: Pergamon Press, 1959: 70—71 [26]Otero T. F., de Larreta-Azelain E.. Polymer[J], 1988, 29: 1522—1527 [27]RONG Guo-Bin(荣国斌), ZHU Shi-Zheng(朱仕正). Structure Determination of Organic CompoundsTables of Spectral Data(波谱数据表有机化合物的结构解析)[M], Shanghai: Eastchina University of Science and Technology, 2002: 255—265 [28]Sezer E., Ustamehmetoglu B., Sarac A. S.. Synth. Met.[J], 1999, 107: 7—17 [29]Morin J. F., Leclerc M., Adès D., Siove A.. Macromol. Rapid. Commun.[J], 2005, 26: 761—778 [30]Guo L., Shi G. Q., Liang Y. Q.. Synth. Met.[J], 1999, 104: 129—135