Synthesis and Characterization of Polyurethanes Containing the NLO-phore Dioxynitrostilbene

Ju Yeon Lee

Korea Polymer Journal, Vol.8, No.3, 137-141, June, 2000

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Synthesis and Characterization of Polyurethanes Containing the NLO-phore Dioxynitrostilbene

Ju Yeon Lee^†

Department of Chemistry, Inje University, 607 Aebang-dong, Kimhae 621-749, Korea

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3,4-Di-(2'-hydroxyethoxy)-4-nitrostilbene (2) was prepared by the reaction of 2-iodoethanol with 3,4-dihydroxy-4-nitrostilbene (1). Diol 2 was condensed with 2,4-toluenediisocyanate, 3,3'-dimethoxy-4,4'-biphenylenediisocyanate, and 1,6-hexamethylenediisocyanate to yield polyurethanes 3,4 and 4 containing the NLO-chromophore. Polymer 3-5 were soluble in common organic solvents such as acetone and DMSO. The glass transition temperatures (T_g) of the resulting polymers 3-5 were observed around 100-114℃. Electrooptic coefficients (r₃₃) of the poled polymer films were in the range of 18-25 pm/V at 633 nm. Polymers 3-5 began to decompose around 250℃ in TGA thermograms.

[References]

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[1] Chemla DS, Zyss J, Nonlinear Optical Properties of Organic Molecules and Crystals, Academic Press, New York, 1987, Vol. 1 and 2 (1987)

[2] Prasad PN, Williams DJ, Introduction to Nonlinear Optical Effects in Molecules and Polymers, John Wiley & Sons, New York, 1991 (1991)

[3] Zyss J, Molecular Nonlinear Optics; Materials, Physics and Devices, Academic Press, Orlando, FL, 1987, 1994

[4] Burland DM, Miller RD, Walsh CA, Chem. Rev., 94(1), 31 (1994)

[5] Dalton LR, Harper AW, Ghosn R, Steiner WH, Ziari M, Fetterman H, Shi Y, Mustacich RV, Jen AKY, Shea KJ, Chem. Mater., 7, 1060 (1995)

[6] Dalton LR, Harper AW, Ghosn R, Laquindanum J, Liang Z, Hubble A, Xu C, Adv. Mater., 7, 519 (1995)

[7] Marks TJ, Ratner MA, Angew. Chem.-Int. Edit., 34, 155 (1995)

[8] Williams DJ, Nonlinear Optical Properties of Organic and Polymeric Materials, ACS Symp. Ser. 233 (1983)

[9] Ranon PM, Shi Y, Steiner WH, Xu CH, Dalton LR, Organic Thin Films for Photonics Application, OSA, 1993, Technical Digest Series Vol. 17, pp 10 (1993)

[10] Han KS, Park SK, Shim SY, Jahng WS, Kim NJ, Bull. Korean Chem. Soc., 19, 1165 (1998)

[11] Han KS, Park SK, Shim SY, Lee YS, Jahng WS, Kim NJ, Bull. Korean Chem. Soc., 19, 1168 (1998)

[12] Becker MW, Sapochak LS, Ghosn R, Xu C, Dalton LR, Chem. Mater., 76, 104 (1994)

[13] Stahelin M, Walsh C, Burland DM, Miller RD, Twieg R, Volksen W, J. Appl. Phys., 94, 31 (1994)

[14] Moon KJ, Shim HK, Lee KS, Zieba J, Prasad PN, Macromolecules, 29(3), 861 (1996)

[15] Woo HY, Shim HK, Lee KS, Polym. J., 32, 8 (2000)

[16] Teng CC, Mann HT, Appl. Phys. Lett., 56, 30 (1990)

[17] Cullinane NM, J. Chem. Soc., 123, 2053 (1923)