5,15-Bis(mesityl)-10,20-bis(4-amino)porphyrin을 포함하는 Copolyimide의 합성

김휘성; 이민호; 김춘호; 김미라; 이진국

Journal of the Korean Industrial and Engineering Chemistry, Vol.10, No.6, 828-831, October, 1999

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5,15-Bis(mesityl)-10,20-bis(4-amino)porphyrin을 포함하는 Copolyimide의 합성

Synthesis of Copolyimide Containing 5,15-Bis(mesityl)-10,20-bis(4-amino)porphyrin

김휘성, 이민호, 김춘호, 김미라, 이진국

초록

Meso-(mesityl)dipyrromethane(MS-DPM)과 4-nitrobenaldehyde로부터 5,15-bis(mesityl)-10,20-bis(4-amino)porphyrin[mesityl-TPP(NH₂)]을 합성하였다. Mesityl-TPP(NH₂)는 UV spectrophotometer[Soret-band(438 nm), Q-band(526, 572, 611 nm)]와 ¹H-NMR spectroscopy에 의해 그 구조를 확인하였다. 3,3`,4,4`-Benzophenone tetracarboxylic dianhydride(BTDA)와 2,2-bis(4-(4-aminophenoxy)-phenyl)hexafluoropropane(BAPHF)를 mesityl-TPP(NH₂)와 축합시켜 porphyrin 구조를 포함하는 copolyimide를 합성하였다. 제조된 copolyimide 역시 UV spectrophotometer [Soret-band (428 nm), Q-band (558 nm, 599 nm)]와 FT-IR spectrophotometer를 이용하여 그 구조를 확인하였고, 열분석 결과 T_g와 T_m은 각각 220.7와 369.2℃였다.

5,15-Bis(mesity)-10,20-bis(4-amino)porphyrin was synthesized with meso-(mesityl)dipyrromethane and 4-nitrobenzaldehyde. It was characterized with ¹H-NMR spectroscopy, UV spectrophotometer, and GC-MASS. In UV spectrum, Soret-band(438 nm) and Q-bands(526, 572, 611 nm) were confirmed. In NMR spectrum, the characteristic peak of porphyrin was detected at -2.65 ppm. Copolyimide containing porphyrin structure was synthesized with mesityl-TPP(NH₂), 3,3`,4,4`-benzophenonetetracarboxylic dianhydride(BTDA) and 2,2-bis(4-(4-aminophenoxy)phenyl) hexafluoropropane(BAPHF) and characterized with UV and FT-IR spectrophotometer. The T_g and T_m of the synthesized copolyimide were 220.7 and 369.2 ℃, respectively.

Keywords:porphyrin;copolymide;Soret band;Q-band;imidization

[References]

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[1] Wagner RW, Lindsey JS, Seth J, Palaniappan V, Bocian DF, J. Am. Chem. Soc., 118(16), 3996 (1996)

[2] Brian AG, Marye AF, Bard AJ, J. Phys. Chem., 93, 4227 (1989)

[3] Takeda Y, Takahara S, Kobayashi Y, Misawa H, Sakuragi H, Tokumaru K, Chem. Lett., 2103 (1990)

[4] Bhardwaj, U.S. Patent, 5,312,896 (1994)

[5] Aota H, Itai Y, Matsumoto A, Kamachi M, Chem. Lett., 2043 (1994)

[6] Aramata K, Kajiwara A, Kamachi M, Macromolecules, 28(13), 4774 (1995)

[7] Peng ZH, Bao ZN, Yu LP, J. Am. Chem. Soc., 116(13), 6003 (1994)

[8] Fleischer EB, Shachter AM, Inorg. Chem., 30, 3763 (1991)

[9] Young R, Chang CK, J. Am. Chem. Soc., 107, 898 (1985)

[10] Manka JS, Lawrence DS, Tetrahedron Lett., 30, 6989 (1989)

[11] Lee CH, Lindsey JS, Tetrahedron, 50, 11427 (1994)

[12] Goll JG, Moore KT, Ghosh A, Therien MJ, J. Am. Chem. Soc., 118(35), 8344 (1996)

[13] Kajiwara A, Aramata K, Kamachi M, Sumi K, Polym. J., 26, 215 (1994)