Hyperbranched Electroactive Azo Polyamide Based on Oligoaniline: Synthesis, Characterization, and Dielectric Properties

Xiaoteng Jia; Danming Chao; Libing He; Hongtao Liu; Tian Zheng; Chengcheng Zhang; Ce Wang

Macromolecular Research, Vol.19, No.11, 1127-1133, November, 2011

DOI10.1007/s13233-011-1114-3 Export Citation

Hyperbranched Electroactive Azo Polyamide Based on Oligoaniline: Synthesis, Characterization, and Dielectric Properties

Xiaoteng Jia, Danming Chao, Libing He, Hongtao Liu, Tian Zheng, Chengcheng Zhang, and Ce Wang^†

Alan G. MacDiarmid Institute, Jilin University, Changchun, 130012, P. R. China

E-mail:

A novel hyperbranched electroactive azo polyamide containing oligoaniline was synthesized by oxidative coupling polymerization. The detailed characteristics of the obtained polyamide were systematically studied by Fourier transform infrared (FTIR) spectra, nuclear magnetic resonance (1H NMR) spectroscopy, and gel permeation chromatography (GPC). The thermogravimetric analysis (TGA) revealed a good thermal resistance of the polymer. The photoisomerization process and doping process of the polymer were monitored with ultraviolet-visible spectroscopy. Further, the electrochemical behavior of the polymer was explored by cyclic voltammogram(CV), and the mechanism of electrochemical oxidation process was studied in detail. The polymer in the HCl-doped form possessed much higher dielectric constants compared with that of the similar linear polymer reported before, mainly due to the highly branched three-dimensional molecular architecture and the high content of oligoaniline segments.

Keywords:hyperbranched;oligoaniline;electroactive;azo;dielectric properties.

[References]

MacDiarmid AG, Angew. Chem. Int. Ed., 40, 2581 (2001)
Heeger AJ, J. Phys. Chem. B, 105(36), 8475 (2001)
McQuade DT, Pullen AE, Swager TM, Chem. Rev., 100(7), 2537 (2000)
Hatchett DW, Josowicz M, Chem. Rev., 108(2), 746 (2008)
Jang J, Ha J, Kim S, Macromol. Res., 15(2), 154 (2007)
Kenwright AM, Feast WJ, Adams P, Milton AJ, Monkman AP, Say BJ, Polymer., 33, 429 (1992)
Kulszewicz-Bajer I, Rozalska I, Kurylek M, New J.Chem., 28, 669 (2004)
Wei ZX, Laitinen T, Smarsly B, Ikkala O, Faul CFJ, Angew. Chem. Int. Ed., 44, 751 (2005)
Cai LT, Cabassi MA, Yoon H, Cabarcos OM, McGuiness CL, Flatt AK, Allara DL, Tour JM, Mayer TS, Nano Lett., 5, 2365 (2005)
Wei ZX, Faul CFJ, Macromol. Rapid Commun., 29(4), 280 (2008)
Canteenwala T, Anantharaj V, Patil SV, Halder M, Chiang LY, J. Macromol. Sci.: Pure Appl. Chem., 39, 1069 (2002)
Quillard S, Corraze B, Poncet M, Mevellec JY, Buisson JP, Evain M, Wang W, MacDiarmid AG, Synth. Met., 137, 921 (2003)
Surwade SP, Agnihotra SR, Dua V, Manohar N, Jain S, Ammu S, Manohar SK, J. Am. Chem. Soc., 131(35), 12528 (2009)
Chen R, Benicewicz BC, Macromolecules, 36(17), 6333 (2003)
Gao JB, Liu DG, Sansinena JM, Wang HL, Adv. Funct. Mater., 14(6), 537 (2004)
Chao DM, Lu XF, Chen JY, Zhao XG, Wang LF, Zhang WJ, Wei Y, J. Polym. Sci. A: Polym. Chem., 44(1), 477 (2006)
Liang SW, Claude J, Xu K, Wang Q, Macromolecules, 41(17), 6265 (2008)
Zhang JF, Chao DM, Cui LL, Liu XC, Zhang WJ, Macromol. Chem. Phys., 210, 1739 (2009)
Fang FF, Lee BM, Choi HJ, Macromol. Res., 18(2), 99 (2010)
Ho CH, Liu CD, Hsieh CH, Hsieh KH, Lee SN, Synth. Met., 158, 63 (2008)
Boye S, Komber H, Friedel P, Lederer A, Polymer, 51(18), 4110 (2010)
Zhang D, Jia D, Zhou Z, Macromol. Res., 17(5), 289 (2009)
Hawker CJ, Lee R, Frechet JM, J. Am. Chem. Soc., 113, 4583 (1991)
Hirao A, Tsunoda Y, Matasuo A, SugiyarnaK, Watanabe T, Macromol. Res., 14, 271 (2006)
Palui G, Banerjee A, J. Phys. Chem. B, 112(33), 10107 (2008)
Basavaraja C, Pierson R, Huh DS, Venkataraman A, Basavaraja S, Macromol. Res., 17(8), 609 (2009)
Yue J, Epstein AJ, Zhong Z, Gallagher PK, MacDiarmid AG, Synth. Met., 41, 765 (1991)
Jeevananda T, Siddaramaiah, Seetharamu S, Saravanan S, Souza LD, Synth. Met., 140, 247 (2004)
Chen L, Yu YH, Mao HP, Lu XF, Yao L, Zhang WJ, Wei Y, Chem. J. Chinese Universities., 9, 1768 (2004)
Chen L, Yu YH, Mao HP, Lu XF, Zhang WJ, Wei Y, Synth. Met., 149, 129 (2005)
Showkat AM, Lee KP, Gopalan AI, Kim SH, Macromol. Res., 15(6), 575 (2007)
Nekrasov AA, Ivanov VF, Vannikov AV, J. Electroanal. Chem., 482(1), 11 (2000)
Guo M, Yan XZ, Kwon Y, Hayakawa T, Kakimoto MA, Goodson T, J. Am. Chem. Soc., 128(46), 14820 (2006)
Wang CC, Song JF, Bao HM, Shen QD, Yang CZ, Adv. Funct. Mater., 18(8), 1299 (2008)
Belaabed B, Lamouri S, Naar N, Bourson P, Hamady SOS, Polym. J., 42, 546 (2010)
Vettegren VI, Zakrevski VA, Smirnov AN, Sudar NT, Phys. Solid State., 52, 1774 (2010)
Lu JX, Moon KS, Kim BK, Wong CP, Polymer, 48(6), 1510 (2007)

[1] MacDiarmid AG, Angew. Chem. Int. Ed., 40, 2581 (2001)

[2] Heeger AJ, J. Phys. Chem. B, 105(36), 8475 (2001)

[3] McQuade DT, Pullen AE, Swager TM, Chem. Rev., 100(7), 2537 (2000)

[4] Hatchett DW, Josowicz M, Chem. Rev., 108(2), 746 (2008)

[5] Jang J, Ha J, Kim S, Macromol. Res., 15(2), 154 (2007)

[6] Kenwright AM, Feast WJ, Adams P, Milton AJ, Monkman AP, Say BJ, Polymer., 33, 429 (1992)

[7] Kulszewicz-Bajer I, Rozalska I, Kurylek M, New J.Chem., 28, 669 (2004)

[8] Wei ZX, Laitinen T, Smarsly B, Ikkala O, Faul CFJ, Angew. Chem. Int. Ed., 44, 751 (2005)

[9] Cai LT, Cabassi MA, Yoon H, Cabarcos OM, McGuiness CL, Flatt AK, Allara DL, Tour JM, Mayer TS, Nano Lett., 5, 2365 (2005)

[10] Wei ZX, Faul CFJ, Macromol. Rapid Commun., 29(4), 280 (2008)

[11] Canteenwala T, Anantharaj V, Patil SV, Halder M, Chiang LY, J. Macromol. Sci.: Pure Appl. Chem., 39, 1069 (2002)

[12] Quillard S, Corraze B, Poncet M, Mevellec JY, Buisson JP, Evain M, Wang W, MacDiarmid AG, Synth. Met., 137, 921 (2003)

[13] Surwade SP, Agnihotra SR, Dua V, Manohar N, Jain S, Ammu S, Manohar SK, J. Am. Chem. Soc., 131(35), 12528 (2009)

[14] Chen R, Benicewicz BC, Macromolecules, 36(17), 6333 (2003)

[15] Gao JB, Liu DG, Sansinena JM, Wang HL, Adv. Funct. Mater., 14(6), 537 (2004)

[16] Chao DM, Lu XF, Chen JY, Zhao XG, Wang LF, Zhang WJ, Wei Y, J. Polym. Sci. A: Polym. Chem., 44(1), 477 (2006)

[17] Liang SW, Claude J, Xu K, Wang Q, Macromolecules, 41(17), 6265 (2008)

[18] Zhang JF, Chao DM, Cui LL, Liu XC, Zhang WJ, Macromol. Chem. Phys., 210, 1739 (2009)

[19] Fang FF, Lee BM, Choi HJ, Macromol. Res., 18(2), 99 (2010)

[20] Ho CH, Liu CD, Hsieh CH, Hsieh KH, Lee SN, Synth. Met., 158, 63 (2008)

[21] Boye S, Komber H, Friedel P, Lederer A, Polymer, 51(18), 4110 (2010)

[22] Zhang D, Jia D, Zhou Z, Macromol. Res., 17(5), 289 (2009)

[23] Hawker CJ, Lee R, Frechet JM, J. Am. Chem. Soc., 113, 4583 (1991)

[24] Hirao A, Tsunoda Y, Matasuo A, SugiyarnaK, Watanabe T, Macromol. Res., 14, 271 (2006)

[25] Palui G, Banerjee A, J. Phys. Chem. B, 112(33), 10107 (2008)

[26] Basavaraja C, Pierson R, Huh DS, Venkataraman A, Basavaraja S, Macromol. Res., 17(8), 609 (2009)

[27] Yue J, Epstein AJ, Zhong Z, Gallagher PK, MacDiarmid AG, Synth. Met., 41, 765 (1991)

[28] Jeevananda T, Siddaramaiah, Seetharamu S, Saravanan S, Souza LD, Synth. Met., 140, 247 (2004)

[29] Chen L, Yu YH, Mao HP, Lu XF, Yao L, Zhang WJ, Wei Y, Chem. J. Chinese Universities., 9, 1768 (2004)

[30] Chen L, Yu YH, Mao HP, Lu XF, Zhang WJ, Wei Y, Synth. Met., 149, 129 (2005)

[31] Showkat AM, Lee KP, Gopalan AI, Kim SH, Macromol. Res., 15(6), 575 (2007)

[32] Nekrasov AA, Ivanov VF, Vannikov AV, J. Electroanal. Chem., 482(1), 11 (2000)

[33] Guo M, Yan XZ, Kwon Y, Hayakawa T, Kakimoto MA, Goodson T, J. Am. Chem. Soc., 128(46), 14820 (2006)

[34] Wang CC, Song JF, Bao HM, Shen QD, Yang CZ, Adv. Funct. Mater., 18(8), 1299 (2008)

[35] Belaabed B, Lamouri S, Naar N, Bourson P, Hamady SOS, Polym. J., 42, 546 (2010)

[36] Vettegren VI, Zakrevski VA, Smirnov AN, Sudar NT, Phys. Solid State., 52, 1774 (2010)

[37] Lu JX, Moon KS, Kim BK, Wong CP, Polymer, 48(6), 1510 (2007)