Preparation of Poly(Alkyl Vinyl Ethers) for Nonlinear Optical Applications 2/Synthesis and Cationic Polymerization of 4'-(2-vinyloxyethoxy)-4-nitrostilbene

Lee JY

Korea Polymer Journal, Vol.3, No.1, 19-24, April, 1995

Lee JY

4'-(2-vinyloxyethoxy)-4-nitrostilbene was prepared by the reaction of 4'-hydroxy-4-nitrostilbene with 2-iodoethyl vinyl ether. the monomer was polymerized with cationic initiators to obtain a poly(ethyl vinyl ether) with 4'-oxy-4-nitrostilbene as a NLO-phore in the side chain. The resulting polymer was soluble in common solvents such as chloroform and DMSO. The inherent viscosities of polymer were in the range of 0.25-0.30 dL/g in chloroform. The polymer showed a good thermal stability in TGA thermogram. Solution-casted films were cloudy and brittle with a T_g of 63℃.

[References]

Lee JY, Polym. Bull., 33(6), 635 (1994)
Lee JY, Polym. Bull., in press
Williams DJ, Angew. Chem.-Int. Edit., 23, 690 (1984)
Prasad PN, Ulrich DR, "Nonlinear Optical and Electroactive Polymers," Plenum Press, New York (1987)
Chemla DS, Zyss J, "Nonlinear Optical Properties of Organic Molecutes and Crystals," vol. 1, 2, Academic Press, New York (1987)
Heeger AJ, Orestein J, Ulrich DR, "Nonlinear Optical Priperties of Polymers," Mater. Res. Soc. Symp. Proc. Vol. 109, Mat. Res. Soc. Pittsburg (1988)
Shen YR, "The Principles of Nonlinear Optics," Wiley, New York (1984)
Robello DR, J. Polym. Sci. A: Polym. Chem., 28, 1 (1990)
Nijhuis S, Rikken GLJA, Havinga EE, Hoeve WT, Wynberg H, Meijer EW, J. Chem. Soc.-Chem. Commun., 1093 (1990)
Ni Z, Leslie TM, Padias AB, Hall HK, Macromolecules, 24, 2100 (1991)
Rondou P, Beylen MV, Samyn C, Sheeren G, Persoons A, Makromol. Chem., 193, 3045 (1992)
Sheeren G, Persoons A, Rondou P, Wiersma J, Beylen MV, Samyn C, Makromol. Chem., 194, 1733 (1993)
Mcculloch IA, Macromolecules, 27(7), 1697 (1994)
Baehr C, Glusen B, Wendorff JH, Staring EG, Macromol. Rapid Commun., 15, 327 (1994)
Vanermen G, Samyn C, Sheeren G, Persoons A, Makomol. Chem., 193, 3057 (1992)
Stenger-Smith JD, Fisher JW, Henry RA, Hoover JM, Lindsay GA, Hayden LM, Macromol. Rapid Commun., 11, 141 (1990)
Fuso F, Padias AB, Hall HK, Macromolecules, 24, 1710 (1991)
Stenger-Smith JD, Fisher JW, Henry RA, Hoover JM, Nadler MP, Nissan RA, Lindsay RA, Lindsay GA, J. Polym. Sci. A: Polym. Chem., 29, 1623 (1991)
Francis CV, White KM, Newmark RA, Stephens MG, Macromolecules, 26, 4379 (1991)
Wright ME, Mullick S, Lackritz HS, Liu LY, Macromolecules, 27(11), 3009 (1994)
Boogers JA, Klaase PT, Devlieger JJ, Tinnemans AH, Macromolecules, 27(1), 205 (1994)
Lindsay GA, Stenger-Smith JD, Henry RA, Hoover JM, Nissan RA, Macromolecules, 25, 6075 (1992)
Xu C, Wu B, Dalton LR, Ranon PM, Shi Y, Steier WH, Macromolecules, 25, 6716 (1992)
Kondo K, Okuda M, Fugitani T, Macromolecules, 26, 7382 (1993)
Campbell D, Dix LR, Rostron P, Eur. Polym. J., 29, 249 (1993)
Lee JY, Polym. Bull., in press
Lee JY, J. Korean Chem. Soc., 39, 327 (1995)
Cullinane NM, J. Chem. Soc., 123, 2053 (1923)
Moore AHF, Org. Syn. Coll., 4, 84 (1963)
Griffin AC, Bhatti AM, Hung RS, in reference 2, pp. 375-391

[1] Lee JY, Polym. Bull., 33(6), 635 (1994)

[2] Lee JY, Polym. Bull., in press

[3] Williams DJ, Angew. Chem.-Int. Edit., 23, 690 (1984)

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

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

[6] Heeger AJ, Orestein J, Ulrich DR, "Nonlinear Optical Priperties of Polymers," Mater. Res. Soc. Symp. Proc. Vol. 109, Mat. Res. Soc. Pittsburg (1988)

[7] Shen YR, "The Principles of Nonlinear Optics," Wiley, New York (1984)

[8] Robello DR, J. Polym. Sci. A: Polym. Chem., 28, 1 (1990)

[9] Nijhuis S, Rikken GLJA, Havinga EE, Hoeve WT, Wynberg H, Meijer EW, J. Chem. Soc.-Chem. Commun., 1093 (1990)

[10] Ni Z, Leslie TM, Padias AB, Hall HK, Macromolecules, 24, 2100 (1991)

[11] Rondou P, Beylen MV, Samyn C, Sheeren G, Persoons A, Makromol. Chem., 193, 3045 (1992)

[12] Sheeren G, Persoons A, Rondou P, Wiersma J, Beylen MV, Samyn C, Makromol. Chem., 194, 1733 (1993)

[13] Mcculloch IA, Macromolecules, 27(7), 1697 (1994)

[14] Baehr C, Glusen B, Wendorff JH, Staring EG, Macromol. Rapid Commun., 15, 327 (1994)

[15] Vanermen G, Samyn C, Sheeren G, Persoons A, Makomol. Chem., 193, 3057 (1992)

[16] Stenger-Smith JD, Fisher JW, Henry RA, Hoover JM, Lindsay GA, Hayden LM, Macromol. Rapid Commun., 11, 141 (1990)

[17] Fuso F, Padias AB, Hall HK, Macromolecules, 24, 1710 (1991)

[18] Stenger-Smith JD, Fisher JW, Henry RA, Hoover JM, Nadler MP, Nissan RA, Lindsay RA, Lindsay GA, J. Polym. Sci. A: Polym. Chem., 29, 1623 (1991)

[19] Francis CV, White KM, Newmark RA, Stephens MG, Macromolecules, 26, 4379 (1991)

[20] Wright ME, Mullick S, Lackritz HS, Liu LY, Macromolecules, 27(11), 3009 (1994)

[21] Boogers JA, Klaase PT, Devlieger JJ, Tinnemans AH, Macromolecules, 27(1), 205 (1994)

[22] Lindsay GA, Stenger-Smith JD, Henry RA, Hoover JM, Nissan RA, Macromolecules, 25, 6075 (1992)

[23] Xu C, Wu B, Dalton LR, Ranon PM, Shi Y, Steier WH, Macromolecules, 25, 6716 (1992)

[24] Kondo K, Okuda M, Fugitani T, Macromolecules, 26, 7382 (1993)

[25] Campbell D, Dix LR, Rostron P, Eur. Polym. J., 29, 249 (1993)

[26] Lee JY, Polym. Bull., in press

[27] Lee JY, J. Korean Chem. Soc., 39, 327 (1995)

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

[29] Moore AHF, Org. Syn. Coll., 4, 84 (1963)

[30] Griffin AC, Bhatti AM, Hung RS, in reference 2, pp. 375-391