광변색성 2-(1',2'-dimethyl-3'-indolyl)-3-(2"-methyl-3"-benzo[<i>b</i>]thiophenyl) maleic anhydride와 폴리스티렌 유도체의 합성과 특성

김준원; 안광현; 김홍두; 장태현

Polymer(Korea), Vol.21, No.3, 512-519, May, 1997

Export Citation

광변색성 2-(1',2'-dimethyl-3'-indolyl)-3-(2"-methyl-3"-benzo[b]thiophenyl) maleic anhydride와 폴리스티렌 유도체의 합성과 특성

2'-dimethyl-3'-indolyl)-3-(2"-methyl-3"-benzo[b] thiophenyl) maleic anhydride and Its Polystyrene Derivatives

김준원, 안광현, 김홍두, 장태현

초록

광변색성 2-(1',2'-dimethyl-3'-indolyl)-3-(2"-methyl-3"-benzo[b] thiophenyl) maleic anhydride (DIMBMA)을 전자고리화 반응에 의해 합성하였다. 새로운 합성 방법은 이전에 발표된 thio-Claisen 자리옮김 반응방법보다 더 나은 수득율을 보였다. 광변색성 DIMBMA을 폴리스티렌에 고착하기 위해 부분적으로 아미노메틸화된 폴리스티렌을 사용하였다. 합성된 DIMBMA은 벤젠이나 폴리스티렌 필름에서 488nm 파장에 의해 쉽게 고리화 반응이 일어나며 그 역반응은 632.8nm나 주위의 빛에 의해 쉽게 윈래 상태로 되돌아감을 보였다. 역반응은 빛이 없는 상태에서는 진행되지 않으며 그 수명은 아주 길었다. Forced Rayleigh scattering을 이용하여 DIMBMA의 확산계수와 홀로그래픽 효능을 측정하였다.

Photochromic 2-(1',2'-dimethyl-3'-indolyl)-3-(2"-methyl-3"-benzo[b] thiophenyl) maleic anhydride (DIMBMA) was synthesized by electrocyclic reaction. The new synthetic route gave a better yield than previously reported trio-Claisen rearrangement method. Partially aminomethylated polystyrene was used to label DIMBMA. DIMBMA in benzene solution or polystyrene film turned into the cyclic form by 488 nm wavelength and using 632.8 nm or ambient light it was easily reverted. The reverse reaction did not proceed in dark condition and its life time seemed extremely long. The forced Rayleigh scattering was used to measure the diffusion coefficient of DIMBMA and its holographic efficiency in benzene solution.

Keywords:photochromism;diffusion coefficient;holographic efficiency;aminomethylated polystyrene;photonics

[References]

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[2] Hornak LA, "Polymers for Lightwave and Integrated Optecs," Marcel Dekker, New York (1992)

[3] Chemla DS, Zyss J, "Nonlinear Optical Properties of Organic Molecules and Crystals," Academic Press, New York (1987)

[4] Prasad PN, Ulrich DR, "Nonlinear Optical and Electroactive Polymers," Plenum Press, New York and London (1987)

[5] Brown GH, "Photochromism," Wiley Interscience, New York (1971)

[6] McArdle CB, "Applied Photochromic Polymer Systems," Chapman and Hall, New York (1992)

[7] Santiago A, Becker R, J. Am. Chem. Soc., 90, 3654 (1968)

[8] Heller HG, Chem. Ind., 193 (1978)

[9] Heller HG, Oliver S, J. Chem. Soc.-Perkin Trans. 1, 1, 197 (1981)

[10] Darcy PJ, Heller HG, Strydom PJ, Whittall J, J. Chem. Soc.-Perkin Trans. 1, 1, 202 (1981)

[11] Heller HG, Langan JR, J. Chem. Soc.-Perkin Trans. 2, 2, 341 (1981)

[12] Glaze AP, Harris SA, Heller HG, Johncock W, Oliver SN, Strydom PJ, Whittall J, J. Chem. Soc.-Perkin Trans. 1, 1, 957 (1985)

[13] Heller HG, Proc. IEEE, 130, 209 (1983)

[14] Urlich K, Port H, Chem. Phys. Lett., 155, 437 (1989)

[15] Irie M, Mohri M, J. Org. Chem., 53, 803 (1988)

[16] Uchida K, Nakayama Y, Irie M, Bull. Chem. Soc. Jpn., 63, 1311 (1990)

[17] Hervet H, Urbach W, Rondelez F, J. Chem. Phys., 68, 2725 (1978)

[18] Leger L, Hervet H, Rondelez F, Macromolecules, 14, 1732 (1981)

[19] Wesson JA, Noh I, Kitano T, Yu H, Macromolecules, 17, 282 (1984)

[20] Kim H, Chang T, Yohanan JM, Wang L, Yu H, Macromolecules, 19, 2737 (1986)

[21] Bergman J, Pelcman B, Tetrahedron Lett., 28, 4441 (1987)