화학공학소재연구정보센터
Journal of Industrial and Engineering Chemistry, Vol.17, No.2, 282-286, March, 2011
Synthesis and properties of poly(N-benzoyl-2-ethynylpyridinium chloride)
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A new ionic polyacetylene with N-benzoylpyridinium substituent was prepared by the activation polymerization of 2-ethynylpyridine by using benzoyl chloride without any additional initiator or catalyst. This reaction proceeded well in homogeneous manner to give a high yield of the polymer (yield: 89%). The initial light-brown solution of 2-ethynylpyridine and benzoyl chloride became a viscous dark-red solution as the polymerization proceeded. The activated acetylenic triple bond of N-benzoyl-2-ethynylpyridinium chloride, formed at first quaternarization process, was susceptible to linear polymerization. This polymer was completely soluble in water, methanol, DMF, and DMSO, and the polymer was found to be mostly amorphous. The instrumental analysis data on the polymer structure revealed that the polymer has conjugated polyene backbone structure with the designed N-benzoylpyridinium substituent. The photoluminescence peak is located at 509 nm corresponding to a photon energy of 2.44 eV. The electrochemical properties of this ionic polyacetylene were also measured and discussed.
  1. Chien JCW, Polyacetylene, Academic Press, New York (1984)
  2. Ito T, Shirakawa H, Ikeda S, J. Polym. Sci. A: Polym. Chem., 12, 11 (1974)
  3. Chiang CK, Fincher CR Jr., Park YW, Heeger AJ, Shirakawa H, Louis EJ, Phys. Rev. Lett., 39, 1098 (1977)
  4. Diaz AF, Kanazawa KK, Gardini GP, J. Chem. Soc., Chem. Commun., 635 (1979)
  5. Gal YS, Choi SK, J. Appl. Polym. Sci., 50, 601 (1993)
  6. Jin SH, Kim MY, Kim JY, Lee K, Gal YS, J. Am. Chem. Soc., 126(8), 2474 (2004)
  7. Karim MA, Cho YR, Park JS, Yoon KJ, Lee SJ, Jin SH, Lee GD, Gal YS, Macromol. Res., 16(4), 337 (2008)
  8. Gal YS, Jin SH, Hyun AR, Park YI, Park JW, Lim KT, Lee WC, J. Ind. Eng. Chem., 14(4), 468 (2008)
  9. Lee SJ, Park JS, Yoon KJ, Kim YI, Jin SH, Kang SK, Gal YS, Kang S, Lee JY, Kang JW, Lee SH, Park HD, Kim JJ, Adv. Funct. Mater., 18(24), 3922 (2008)
  10. Lee SJ, Park JS, Song M, Shin IA, Kim YI, Lee JW, Kang JW, Gal YS, Kang S, Lee JY, Jung SH, Kim HS, Chae MY, Jin SH, Adv. Funct. Mater., 19(14), 2205 (2009)
  11. Masuda T, Higashimura T, Acc. Chem. Res., 17, 51 (1981)
  12. Masuda T, J. Polym. Sci. A: Polym. Chem., 45(2), 165 (2007)
  13. Kwak G, Jin SH, Park JW, Gal YS, Macromol. Chem. Phys., 209, 1769 (2008)
  14. Beaujuge PM, Reynolds JR, Chem. Rev., 110(1), 268 (2010)
  15. Choi HK, Jin SH, Park JW, Jung MJ, Gal YS, J. Ind. Eng. Chem., 16(2), 214 (2010)
  16. Park YW, Chem. Soc. Rev., 39, 2428 (2010)
  17. Sherwood DES, Williams JE, Sponsler MB, J. Polym. Sci. A: Polym. Chem., 47(4), 1061 (2009)
  18. Choi SK, Gal YS, Jin SH, Kim HK, Chem. Rev., 100(4), 1645 (2000)
  19. Lam JWY, Tang BZ, Acc. Chem. Res., 38, 745 (2005)
  20. Buchmeiser MR, Adv. Polym. Sci., 176, 89 (2005)
  21. Gal YS, Lee WC, Jin SH, Lim KT, Jang SH, Lyoo WS, Han E, Kim SY, Macromol. Res., 15(3), 267 (2007)
  22. Lee IS, Kwak YW, Lee HD, Gal YS, J. Ind. Eng. Chem., 14(6), 720 (2008)
  23. Okamoto Y, Alia D, Chem. Ind., 1311 (1964)
  24. Simionescu CI, Dumitrescu S, Percec V, Diaconu IR, Mater. Plas., 15, 69 (1978)
  25. Gal YS, Cho HN, Kwon SK, Choi SK, Polym.(Korea), 12(1), 30 (1988)
  26. Gal YS, Lee WC, Gui TL, Lee SS, Bae JS, Kim BS, Jang SH, Jin SH, Bull. Kor. Chem. Soc., 22, 183 (2001)
  27. Gal YS, Jin SH, Gui TL, Lee WC, Yun NG, Park SH, Lee SS, Bae JS, J. Ind. Eng. Chem., 11(3), 432 (2005)
  28. Epstein AJ, Wang YZ, Jessen SW, Blatchford JW, Gebler DD, Lin LB, Gustafson TL, Swager TM, MacDiarmid AG, Macromol. Symp., 116, 27 (1997)
  29. Spiliopoulos IK, Mikroyannidis JA, J. Polym. Sci. A: Polym. Chem., 39(14), 2454 (2001)
  30. Yang SY, Rubner MF, J. Am. Chem. Soc., 124(10), 2100 (2002)
  31. Subramanyam S, Blumstein A, Macromol. Chem. Rapid Commun., 12, 23 (1991)
  32. Subramanyam S, Blumstein A, Macromolecules., 24, 2668 (1991)
  33. Rubinsztajn S, Fife WK, Zeldin M, Tetrahedron Lett., 33, 1821 (1992)
  34. Blumstein A, Samuelson L, Adv. Mater., 10(2), 173 (1998)
  35. Ranganathan P, Fife WK, Zeldin M, J. Polym. Sci. A: Polym. Chem., 28, 2771 (1990)
  36. Fife WK, Zeldin M, Ranganathan P, J. Org. Chem., 55, 5610 (1990)
  37. Iwase Y, Kondo K, Kamada K, Ohta K, J. Polym. Sci. A: Polym. Chem., 40(20), 3534 (2002)
  38. Gal YS, Jin SH, Bull. Kor. Chem. Soc., 25, 777 (2004)
  39. Gal YS, Lee WC, Kim SY, Park JW, Jin SH, Koh KN, Kim SH, J. Polym. Sci. A: Polym. Chem., 39(18), 3151 (2001)
  40. Gal YS, Jin SH, Park JW, J. Polym. Sci. A: Polym. Chem., 45(23), 5679 (2007)
  41. Gal YS, Jin SH, Park JW, Lim KT, Koh K, Han SC, Lee JW, Curr. Appl. Phys., 7(5), 517 (2007)
  42. Gal YS, Suh NH, Lee WC, Jin SH, Park JW, Lyoo WS, Shim SY, Lim KT, Mol.Cryst. Liq. Cryst., 491, 348 (2008)
  43. Gal YS, Jin SH, Park JW, J. Appl. Polym. Sci., 110(2), 719 (2008)
  44. Katritzky AR, Schwarz QA, Rubino O, Markees DG, Helv. Chim. Acta., 67, 939 (1984)
  45. Bard AJ, Faulker LR, Electrochemical Methods, Wiley, New York, (Chapters 3, 6 and 10). (1980)
  46. Ko JM, Rhee HW, Park SM, Kim CY, J. Electrochem. Soc., 137, 905 (1990)