Abstract
In this paper, novel poly(esterimide)s with attached as a side group azobenzene chromophores are presented. The polymers differing in substituents on the azobenzene moieties and chromophore concentration. Azopolymers were obtained by a two-step synthetic approach. This include the preparation of a precursor poly(esterimide) with benzene moiety pendant from main chains, followed by the covalent bonding of the NLO chromophores onto the polyimide backbone by a post-azo-coupling reaction using the following coupling components: p-nitroaniline, 2-cyan-4-nitroanilin, 2,4-dinitroaniline and Disperse Orange 3. The precursor poly(esterimide) was obtained from synthesized 2,2′[N-phenylethyloaniline-di(4-estro-1,2-dicarboxylic)]anhydride and 4,4′-methylene bis(2,6-dimethylaniline). The degree of functionalization of the poly(esterimide)s was estimated by UV-vis spectroscopy. The obtained polymers were characterized and evaluated by FT-IR, 1H NMR, X-ray, UV-vis, DSC and TGA. The results showed the azopolymers exhibited high glass transition temperatures (Tg=159–224 °C), high thermal stability with decomposition temperatures in the range of 311–334 °C and good solubilities in common organic solvents. First time two-photon absorption (TPA) coefficient in cast films of amorphous azopoly(esterimide)s was measured using Z-scan experiment which was performed with femtosecond laser pulses 100 fs at 800 nm. The TPA coefficient was determined to be in the range of 1.54–11.69cm/GW.
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D. R. Kanis, M. A. Ratner, and T. J. Marks, Chem. Rev., 94, 195 (1994).
T. C. Lin, S. J. Chung, K. S. Kim, X. P. Wang, G. S. He, J. Swiatkiewica, H. E. Pudavar, P. N. Prasad, and K. S. Lee, in “Advances in Polymer Science,” Springer, Berlin, 2003, vol. 161, p 157.
H. J. Lee, J. Sohn, J. Hwang, and S. Y. Park, Chem. Mater., 16, 456 (2004).
T. Baldacchini, C. N. LaFratta, R. A. Farrer, M. C. Teich, B. E. A. Saleh, M. J. Naughton, and J. T. Fourkas, J. Apply. Phys., 95, 6072 (2004).
Z. Sekkat, H. Ishitobi, and S. Kawata, Opt. Commun., 222, 269 (2003).
C. C. Corredor, Zh.-L. Huang, K. D. Belfied, A. R. Morales, and M. V. Bondar, Chem. Mater., 19, 5165 (2007).
B. R. Cho, K. H. Son, S. H. Lee, Y.-S. Song, Y.-K. Lee, S. G.-J. Jeon, J. H. Choi, H. Lee, and M. Cho, J. Am. Chem. Soc., 123, 10039 (2001).
Y.-G. Liu, Y. Sui, J. Yin, J. Gao, Z.-K. Zhu, D.-Y. Huang, and Z.-G. Wang, J. Appl. Polym. Sci., Part A, 76, 290 (2000).
S. K. Yesodha, Ch. K. S. Pillai, and N. Tsutsumi, Prog. Polym. Sci. Part A, 29, 45 (2004).
M. R. Cardoso, U. M. Neves, L. Misoguti, Zh. Ye, X. R. Bu, and C. R. Mendonca, Opt. Mater., 28, 1118 (2006).
M. Maeda, H. Ishitobi, Z. Sekkat, and S. Kawata, Appl. Phys. Lett., 85, 351 (2004).
L. Yang, G. Wang, J. Wang, G. Wang, and Z. Xu, Optik, 113, 189 (2002).
X. Yang, L. Hong, G. Ma, Ch. Li, H. Xing, Y. Xu, and E. Liang, Opt. Commun., 272, 521 (2007).
C. R. Mendonca, U. M. Neves, L. De Boni, A. A. Andrade, D. S. dos Santos Jr., F. J. Pavinatto, S. C. Zilio, L. Misoguti, and O. N. Oliveria Jr., Opt. Commun., 273, 435 (2007).
H. Ishitobi, Z. Sekkat, and S. Kawata, J. Chem. Phys., 125, 164718 (2006).
H. L. Hampsch, J. Yang, G. K. Wong, and J. M. Torkensol, Macromolecules, 21, 526 (1988).
M. Cha, W. E. Torruellas, G. I. Stegeman, W. H. G. Horsthuis, G. R. Mohlmann, and J. Meth, Appl. Phys. Lett., 65, 2648 (1994).
M. Samoc, A. Samoc, and B. Luther-Davies, Synth. Met., 109, 79 (2000).
J.-P. Yang, Chem. Phys. Lett., 243, 129 (1995).
F. Meng, J. Mi, Sh. Qian, K. Chen, and H. Tian, Polymer, 44, 6851 (2003).
X. Chen, J. Zhang, H. Zhang, Z. Jiang, G. Shi, Y. Li, and Y. Song, Dyes Pigm., 77, 223 (2008).
J. Y. Do, S. K. Park, J.-J. Ju, S. Park, and M.-H. Lee, Opt. Mater., 26, 223 (2004).
H. Saadeh, L. Wang, and L. Yu, Macromolecules, 33, 1570 (2000).
J. Luo, J. Qin, H. Kang, and Ch. Ye, Chem. Mater., 13, 927 (2001).
T.-A. Chen, A. K.-Y. Jen, and Y. Cai, Macromolecules, 29, 535 (1996).
W. N. Leng, Y. M. Zhou, Q. H. Xu, and J. Z. Liu, Polymer, 42, 7749 (2001).
Y.-G. Liu, Y. Sui, J. Yin, J. Gao, Z.-K. Zhu, D.-Y. Huang, and Z.-G. Wang, J. Appl. Polym. Sci., 76, 290 (2000).
E. Ortyl, S. Kucharski, and T. Gotszalk, Thin Solid Films, 479, 288 (2005).
E. Schab-Balcerzak, B. Sapich, J. Stumpe, A. Sobolweska, and A. Miniewicz, e-polymers, 021 (2006).
M. Chen, L. R. Dalton, L. P. Yu, Y. Q. Shi, and W. H. Steier, Macromolecules, 25, 4032 (1992).
R. Janik, S. Kucharski, A. Kubanska, and B. Lyko, Polish J. Chem., 75, 242 (2001).
D. Sek, E. Schab-Balcerzak, and E. Grabiec, Polymer, 39, 7001 (1998).
Y.-G. Liu, Y. Sui, J. Yin, J. Gao, Z.-K. Zhu, D.-Y. Huang, and Z.-G. Wang, J. Appl. Polym. Sci., 76, 290 (2000).
A. K.-Y. Jen, K. J. Drost, V. P. Rao, Y. Cai, Y.-J. Liu, R. M. Mininni, J. T. Kenney, E. S. Binkley, S. R. Marder, L. R. Dalton, and Ch. Xu, Polym. Prepr., 35, 130 (1994).
D. M. Munoz, J. G. de la Campa, J. de Abajo, and A. E. Lozano, Macromolecules, 40, 8225 (2007).
I. Zhao, Z. Yuxia, Z. Jiayun, and S. Yuquan, Eur. Polym. J., 36, 2418 (2000).
E. Schab-Balcerzak and D. Sek, High Perform. Polym., 13, 45 (2001).
Y. He, J. Yin, P. Che, and X. Wang, Eur. Polym. J., 42, 292 (2006).
E. Schab-Balcerzak, B. Sapich, and J. Stumpe, Polymer, 46, 49 (2005).
J. Wang, W. F. Cao, J. H. Su, H. Tian, Y. H. Huang, and Z. R. Sun, Dyes Pigm., 57, 171 (2003).
B. Jarzabek, J. Weszka, M. Domanski, J. Jurusik, and J. Cisowski, J. Non-Cryst. Solids, 354, 856 (2008).
B. Jarzabek, J. Weszka, A. Burian, and G. Pocztowski, Thin Solid Films, 279, 204 (1996).
M. Sheik-Bahae, M. Ieee, A. A. Said, T.-H. Wei, and D. J. Hagan, J. Quantum Electronics, 26, 760 (1990).
L. De Boni, J. J. Rodrigues Jr., D. S. dos Santos Jr., C. H. T. P. Silva, D. T. Balogh, O. N. Oliveira Jr., S. C. Zilio, L. Misoguti, and C. R. Mendonca, Chem. Phys. Lett., 361, 209 (2002).
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Siwy, M., Jarzabek, B., Switkowski, K. et al. Novel Poly(esterimide)s Containing a Push-Pull Type Azobenzene Moiety-Synthesis, Characterization and Optical Properties. Polym J 40, 813–824 (2008). https://doi.org/10.1295/polymj.PJ2008076
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DOI: https://doi.org/10.1295/polymj.PJ2008076