Macromolecular Research, Vol.12, No.4, 407-412, August, 2004
Synthesis and Properties of Poly[2-ethynyl-N-(p-hydroxyphenylethyl) pyridinium bromide] and Poly[2-ethynyl-N-(p-hydroxyphenylethyl) pyridinium tetraphenylborate]
E-mail:
A new hydroxyl group-containing conjugated ionic polymer, 2-ethynyl-N-(p-hydroxyphenylethyl)
pyridinium bromide], was synthesized by the activated polymerization of 2-ethynylpyridine with p-(2-bromoethyl) phenol without any additional initiator or catalyst. The polymerization proceeded well to give a moderate yield (65%) of polymer at a reaction temparature of 90 ℃. Another polymer, poly[2-ethynyl-N-(p-hydroxyphenylethyl) pyridinium tetraphenylborate], was readily prepared by the ion-exchange reaction of poly[2-ethynyl-N-(phydroxyphenylethyl)
pyridinium bromide] with sodium tetraphenylborate. These polymers were completely soluble
in organic solvents such as DMF, DMSO, and acetone, but insoluble in water and ether. Instrumental analyses, such as NMR, IR, and UV-Vis spectroscopies, indicated that the new materials have conjugated polymer backbone systems with the designed substituents and counter anions. X-Ray diffraction analyses of the polymers indicated that they were mostly amorphous.
Keywords:conjugated polymer;2-ethynylpyridine;characterization;ion-exchange reaction;sodium tetraphenylborate
- Shirakawa H, Louis EJ, MacDiarmid AG, Chiang CK, Heeger AJ, Chem. Commun., 578 (1977)
- Chiang CK, Fincher CR, Park YW, Heeger AJ, Shirakawa H, Louis EJ, Phys. Rev. Lett., 39, 1098 (1977)
- Shirakawa H, Angew. Chem.-Int. Edit., 40, 2574 (2001)
- Ito T, Shirakawa H, Ikeda S, J. Polym. Sci. A: Polym. Chem., 12, 11 (1974)
- Ito T, Shirakawa H, Ikeda S, J. Polym. Sci. A: Polym. Chem., 13, 1943 (1975)
- Diaz AF, Kanazawa KK, Gardini GP, Chem. Commun., 635 (1979)
- Kertesz M, Lee YS, J. Phys. Chem., 91, 2690 (1987)
- Diaz AF, Chem. Ser., 17, 142 (1981)
- Tourillon G, Garnier F, J. Electroanal. Chem., 135, 173 (1982)
- Masuda T, Higashimura T, Accounts Chem. Res., 17, 51 (1981)
- Choi SK, Lee JH, Kang SJ, Jin SH, Prog. Polym. Sci, 22, 693 (1997)
- Choi SK, Gal YS, Jin SH, Kim HK, Chem. Rev., 100(4), 1645 (2000)
- Sanda F, Kawaguchi T, Masuda T, Kobayashi N, Macromolecules, 36(7), 2224 (2003)
- Cheuk KKL, Lam JWY, Chen JW, Lai LM, Tang BZ, Macromolecules, 36(16), 5947 (2003)
- Gal YS, Jin SH, Lee HJ, Kim SH, Lee WC, Choi SK, Macromol. Res., 11(2), 80 (2003)
- Jin SH, Jin JY, Kim YI, Park DK, Gal YS, Macromol. Res., 11(6), 501 (2003)
- Anders U, Kuyken O, Buchmeiser MR, J. Mol. Catal. A-Chem., 213, 89 (2004)
- Gal YS, Jin SH, Choi SK, J. Mol. Catal. A-Chem., 213, 115 (2004)
- Gal YS, Choi SK, J. Appl. Polym. Sci., 50, 601 (1993)
- Nagai K, Masuda T, Nakagawa T, Freeman BD, Finnau I, Prog. Polym. Sci, 26, 721 (2001)
- Gao GZ, Sanda F, Masuda T, Macromolecules, 36(11), 3938 (2003)
- Lam JWY, Dong YP, Cheuk KKL, Tang BZ, Macromolecules, 36(21), 7927 (2003)
- Hwang LS, Ko JM, Rhee HW, Kim CY, Synth. Met., 55-57, 3671 (1993)
- Halvorson C, Hays A, Kraabel B, Wu R, Wudl F, Heeger AJ, Science, 265, 1215 (1994)
- Shiga K, Inoguchi T, Mori K, Kondo K, Kamada K, Tawa K, Ohta K, Maruo T, Mochizuki E, Kai Y, Macromol. Chem. Phys., 202, 257 (2001)
- Tada K, Hidayat R, Teraguchi M, Masuda T, Yoshino K, Jpn. J. Appl. Phys., 35, 1138 (1996)
- Gal YS, Lee WC, Kim SY, Park JW, Jin SH, Koh KN, Kim SH, J. Polym. Sci. A: Polym. Chem., 39(18), 3151 (2001)
- Xie Z, Lam JWY, Dong Y, Qiu C, Kwok HS, Tang BZ, Opt. Mater., 21, 231 (2002)
- Lam JWY, Law CK, Dong Y, Wang J, Ge W, Tang BZ, Opt. Mater., 21, 321 (2002)
- Gal YS, Jung B, Lee WC, Choi SK, Polym.(Korea), 16, 597 (1992)
- Gal YS, J. Macromol. Sci.-Pure Appl. Chem., A31, 703 (1994)
- Russo MV, Iucci G, Polzonetti G, Furlani A, Polymer, 33, 4401 (1992)
- Gal YS, Jung B, Kim JH, Lee WC, Choi SK, J. Macromol. Sci.-Pure Appl. Chem., A31, 1177 (1994)
- Kim YH, Kwon SK, Bull. Korean Chem. Soc., 18, 125 (1997)
- Gal YS, Lee WC, Jin SH, Choi SK, Korea Polym. J., 8, 231 (2000)
- Blumstein A, Subramanyam S, U. S. Patent 5,037,916 (1991)
- Davidov BE, Krentsel BA, Kchutareva GV, J. Polym. Sci. Part C, 16, 1365 (1967)
- Kawasaki M, Masuda T, Higashimura T, Polym. J., 15, 767 (1983)
- Subramanyam S, Blumstein A, Macromolecules, 24, 2668 (1991)
- Balogh L, Blumstein A, Macromolecules, 28(17), 5691 (1995)
- Gal YS, Chem. Commun., 327 (1994)
- Gal YS, Lee WC, Kim SH, Lee SS, Jwa ST, Park SH, J. Macromol. Sci.-Pure Appl. Chem., A36, 429 (1999)
- Gal YS, Jin SH, Gui TL, Lee HJ, Kim SY, Kim DW, Ko JM, Chun JH, Jang SH, Kim BS, Lee WC, J. Macromol. Sci.-Pure Appl. Chem., A40, 401 (2003)
- Gui TL, Jin SH, Park JW, Lim KT, Kim SY, Gal YS, Mat. Sci & Eng. C., 24, 217 (2004)
- Gal YS, Jin SH, Bull. Korean Chem. Soc., 25, 777 (2004)
- Gal YS, Cho HN, Kwon SK, Choi SK, Polym.(Korea), 12(1), 30 (1988)
- Gal YS, Lee SS, Bae JS, Kim BS, Jang SH, Jin SH, Bull. Korean Chem. Soc., 20, 451 (1999)