화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Journal of Industrial and Engineering Chemistry, Vol.18, No.1, 55-60, January, 2012
DOI10.1016/j.jiec.2011.11.081  Export Citation
Electro-optical and electrochemical properties of an ionic polyacetylene derivative with azobenzene anisole moieties
Yeong-Soon Gal†, Sung-Ho Jin1, Jong-Wook Park2, Sung-Hoon Kim3, Won Seok Lyoo4, and Kwon Taek Lim5
  • Polymer Chemistry Laboratory, College of Engineering, Kyungil University, Gyeongsan 712-701, Gyeongsangbuk-Do, Republic of Korea
  • 1Department of Chemistry Education, Pusan National University, Busan 609-735, Republic of Korea
  • 2Department of Chemistry and Center for Display Res., The Catholic University of Korea, Bucheon 420-743, Republic of Korea
  • 3Department of Textile System Engineering, Kyungpook National University, Daegu 702-701, Republic of Korea
  • 4School of Textiles, Yeungnam University, Gyeongsan 712-749, Republic of Korea
  • 5Division of Image and Information Engineering, Pukyong National University, Busan 608-739, Republic of Korea
E-mail:
An ionic polyacetylene derivative with azoanisole moieties was prepared by the activated polymerization of 2-ethynylpyridine by using 4-[4-(9-bromononyloxy)phenylazo]anisole without any additional initiator or catalyst in high yield. The chemical structure of poly[2-ethynyl-N-(p-methoxyphenylazophenyl) oxynonylpyridinium bromide] (PEMPB) was characterized by instrumental methods such as NMR (1H and 13C), IR, UV.vis spectroscopies to have a conjugated polymer backbone system with the designed azobenzene moieties as substituents. This polymer was completely soluble in organic solvents and well processible. The electrochemical and electro-optical properties of PEMPB were studied. The cyclovoltammograms of this polymer exhibited the irreversible electrochemical behaviors between the oxidation and reduction peaks. The oxidation current density of PEMPB versus the scan rate is approximately linear relationship in the range of 30 mV/s-120 mV/s. The exponent of scan rate, x value of PEMPB, is found to be 0.6. The absorption spectrum starts around 700 nm and shows a characteristic absorption band at visible region of 464 nm due to the π → π* interband transition of the polymer backbone, which is a peak of the conjugated polyene backbone. The photoluminescence spectrum showed that the PL peak is located at 539 nm corresponding to the photon energy of 2.30 eV.
Keywords:Polyacetylene;Conjugated polymer;Azobenzene;2-Ethynylpyridine;Cyclovoltammogram;Photoluminescence
  1. Burroughes JH, Bradley DDC, Brown AR, Marks RN, Mackay K, Friend RH, Burns PL, Holmes AB, Nature., 347, 539 (1990)
  2. Jin SH, Kim MY, Kim JY, Lee K, Gal YS, J. Am. Chem. Soc., 126(8), 2474 (2004)
  3. Shirota Y, Kageyama H, Chem. Rev., 104, 953 (2007)
  4. Lo SC, Burn PL, Chem. Rev., 104, 1097 (2007)
  5. Menard E, Meitl MA, Sun Y, Park JU, Shir DJL, Nam YS, Jeon S, Rogers JA, Chem. Rev., 104, 1117 (2007)
  6. Park JH, Cho NS, Jung YK, Cho HJ, him HK, Kim H, Lee YS, Org. Electron., 9, 272 (2008)
  7. Jeon SO, Jeon YM, Kim JW, Lee CW, Gong MS, Org. Electron., 9, 522 (2008)
  8. Chiang CK, Fincher CR, Park YW, Heeger AJ, Shirakawa H, Louis EJ, MacDiarmid AG, Phys. Rev. Lett., 39, 1098 (1977)
  9. Ito T, Shirakawa H, Ikeda S, J. Polym. Sci. A: Polym. Chem., 12, 11 (1974)
  10. Masuda T, Higashimura T, Acc. Chem. Res., 17, 51 (1981)
  11. Choi SK, Lee JH, Kang SJ, Jin SH, Prog. Polym. Sci., 22, 693 (1997)
  12. Choi SK, Gal YS, Jin SH, Kim HK, Chem. Rev., 100(4), 1645 (2000)
  13. Anders U, Nuyken O, Buchmeiser MR, J. Mol. Catal. A-Chem., 213(1), 89 (2004)
  14. Gal YS, Jin SH, Choi SK, J. Mol. Catal. A-Chem., 213(1), 115 (2004)
  15. Lam JWY, Tang BZ, Acc. Chem. Res., 38, 745 (2005)
  16. Gal YS, Jin SH, Park JW, J. Polym. Sci. A: Polym. Chem., 45(23), 5679 (2007)
  17. Kwak G, Jin SH, Park JW, Gal YS, Macromol. Chem. Phys., 209, 1969 (2008)
  18. Choi SH, Kim BS, Frisbie CD, Science., 320, 1482 (2008)
  19. Blumstein A, Subramanyam S, US Patent no. 5,037,916 (1991)
  20. Subramanyam S, Blumstein A, Macromolecules., 24, 2668 (1991)
  21. Gal YS, Chem. Commun., 327 (1994)
  22. Gal YS, Lee WC, Choi SK, Bull. Korean Chem. Soc., 18, 265 (1997)
  23. Gal YS, Lee WC, Kim SY, Park JW, Jin SH, Koh KN, Kim SH, J. Polym. Sci. A: Polym. Chem., 39(18), 3151 (2001)
  24. Gal YS, Jin SH, Bull. Korean Chem. Soc., 25, 777 (2004)
  25. Gal YS, Jin SH, Lee WC, Kim SY, Macromol. Res., 12(4), 407 (2004)
  26. Gal YS, Jin SH, Lim KT, Kim SH, Lyoo WS, Lee CJ, Park JW, Kim SY, Mol.Cryst. Liq. Cryst., 462, 189 (2007)
  27. Gal YS, Jin SH, Park JW, Lim KT, Koh K, Han SC, Lee JW, Curr. Appl. Phys., 7(5), 517 (2007)
  28. Gal YS, Jin SH, Park JW, J. Appl. Polym. Sci., 110(2), 719 (2008)
  29. Choi HK, Jin SH, Park JW, Jung MJ, Gal YS, J. Ind. Eng. Chem., 16(2), 214 (2010)
  30. Gal YS, Jin SH, Park JW, Lim KT, J. Ind. Eng. Chem., 17(2), 282 (2011)
  31. Blumstein A, Samuelson L, Adv. Mater., 10(2), 173 (1998)
  32. Kumar GS, Neckers DC, Chem. Rev., 89, 1915 (1989)
  33. Ikeda T, Tsutsumi O, Science, 268(5219), 1873 (1995)
  34. Rau H, in: Rabek JK (Ed.), Photochemistry and Photophysics, vol. 2, CRC Press, Boca Raton, FL, 119 (1990)
  35. Natansohn A, Rochon P, Chem. Rev., 102(11), 4139 (2002)
  36. Gui TL, Jin SH, Park JW, Ahn WS, Koh KN, Kim SH, Gal YS, Opt. Mater., 21, 637 (2002)
  37. Gal YS, Jin SH, Kim SH, J. Ind. Eng. Chem., 12(2), 235 (2006)
  38. Gal YS, Cho HN, Kwon SK, Choi SK, Polym.(Korea), 12(1), 30 (1988)
  39. Gal YS, Choi SK, J. Appl. Polym. Sci., 50, 601 (1993)
  40. Simionescu CI, Dumitrescu S, Percec V, Diaconu I, Materiale Plastice (Romania)., 15, 69 (1978)
  41. Okawa H, Kurosawa K, Wada T, Sasabe H, Synth. Met., 71, 1657 (1995)
  42. Balogh L, Blumstein A, Macromolecules., 28, 25 (1998)
  43. Zhou PG, Blumstein A, Polymer, 38(3), 595 (1997)
  44. Gui TL, Jin SH, Lee WC, Park JW, Koh K, Kim SH, Lee SS, Bae JS, Kim SY, Gal YS, Curr. Appl. Phys., 5(1), 23 (2005)
  45. Gal YS, Jin SH, Lim KT, Kim SH, Koh K, Curr. Appl. Phys., 5(1), 38 (2005)
  46. Kim SH, Lee SJ, Park SY, Suh HJ, Jin SH, Gal YS, Dyes Pigm., 68, 61 (2006)
  47. Park JW, Lee JH, Ko JM, Cho HN, Choi SK, J. Polym. Sci. A: Polym. Chem., 32(14), 2789 (1994)
  48. Bard AJ, Fauker LR, Electrochemical Methods, Wiley, New York, 1980 (Chapters 3, 6 and 10).
  49. Gui TL, Jin SH, Park JW, Koh K, Kim SH, Lim KT, Gal YS, Cryst. Liq. Cryst., 425, 237 (2004)
  50. Ko JM, Rhee HW, Park SM, Kim CY, J. Electrochem. Soc., 137, 905 (1990)