화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Macromolecular Research, Vol.20, No.6, 614-622, June, 2012
DOI10.1007/s13233-012-0088-0  Export Citation
Synthesis and Characterization of Novel Photoactive, Thermally Stable, and Organosoluble Polymers Based on Carbazole and Imidazole Derivatives in the Main-Chain
Mousa Ghaemy†, Farzaneh Hashemi Nasr, Raouf Alizadeh, and Mehdi Taghavi
  • Polymer Chemistry Research Laboratory, Faculty of Chemistry, University of Mazandaran, Babolsar, 47416-95447, I.R. Iran
E-mail:
A series of novel polyamides (PAs) bearing substituted carbazole and imidazole rings in the main-chain were successfully synthesized via direct phosphorylation polycondensation between a new diamine, 5,5'-(9-octyl-carbazole-3,6-diyl)bis[4-phenyl-2-(4-amino-phenyl)-1H-imidazole], and various commercially available dicarboxylic acids. All intermediates and polymers were fully characterized by FTIR, NMR, and elemental analysis. These polymers were obtained in good yields with inherent viscosities of 0.42-0.55 dL/g and number average molecular weights (Mn) in the range of 24,875-31,720 g/mol molecular weight distribution (MWD=1.57-2.5). They exhibited excellent solubility in common polar aprotic organic solvents. These polymers had high glass transition temperatures (Tg)s (204-309 ℃) and their temperatures at 10% weight loss (T10%) were found to be in the range of 404-511 ℃ in nitrogen. They exhibited strong UV absorption with maxima at 320-335 nm, and their photoluminescence (PL) efficiency was affected by their chemical structure; PL quantum yields were in the range of 4%-34%. The aliphatic PAs emitted blue light at λe.max=465 nm, while the aromatic PAs emitted green light at λe.max=490-510 nm in NMP solution.
Keywords:polyamides;fluorescent;solubility;thermal properties;carbazole;imidazole.
  1. Garcia JM, Garcia FC, Serna F, de la Pena JL, Prog. Polym. Sci., 35, 623 (2010)
  2. Imai Y, React. Funct. Polym., 30(1), 3 (1996)
  3. Hearle JWS, High-Performance Fibres, Woodhead Publishing Ltd, Cambridge (2001)
  4. Mark HF, Encyclopedia of Polymer Science and Technology Wiley Interscience, New York (2004)
  5. Ge ZY, Yang SY, Tao ZQ, Liu JG, Fan L, Polymer, 45(11), 3627 (2004)
  6. Hsiao SH, Chen CW, Liou GS, J. Polym. Sci. A: Polym. Chem., 42(13), 3302 (2004)
  7. Ghaemy M, Alizadeh R, React. Funct. Polym., 71, 425 (2011)
  8. Ferrero E, Espeso JF, De La Campa JG, De Abajo J, Lozano AE, J. Polym. Sci. A: Polym. Chem., 40(21), 3711 (2002)
  9. Ghaemy M, Mojtaba S, Nasab A, Alizadeh R, J. Appl. Polym. Sci., 116(6), 3725 (2010)
  10. Liaw DJ, Hsu PN, Chen JJ, Liaw BY, Hwang CY, J. Polym. Sci. A: Polym. Chem., 39(10), 1557 (2001)
  11. Ghaemy M, Behmadi H, Alizadeh R, Chin. Chem. Lett., 20, 961 (2009)
  12. Chauveau E, Marestin C, Schiets F, Mercier R, Green Chem., 12, 1018 (2010)
  13. Chauveau E, Marestin C, Martin V, Mercier R, Polymer, 49(24), 5209 (2008)
  14. Wang LM, Wang YH, Tian H, Yao YF, Shao JH, Liu B, J. Fluor. Chem., 127, 1570 (2006)
  15. Ghaemy M, Nasab SMA, Polym. J., 42, 648 (2010)
  16. Ghaemy M, Nasab SMA, React. Funct. Polym., 70, 306 (2010)
  17. Shin MG, Thangaraju K, Kim SO, Park JW, Kim YH, Kwon SK, Org. Electron., 12, 785 (2011)
  18. Cloutet E, Olivero C, Ades D, Castex MC, Siove A, Polymer, 43(12), 3489 (2002)
  19. Morin JF, Leclerc M, Ades D, Siove A, Macromol. Rapid Commun., 26(10), 761 (2005)
  20. Grazulevicius JV, Strohriegl P, Pielichowski J, Pielichowski K, Prog. Polym. Sci., 28, 1297 (2003)
  21. Bisvvas M, Das SK, Polymer., 23, 1713 (1982)
  22. Angiolini L, Giorgini L, Li HW, Golemme A, Mauriello F, Termine R, Polymer, 51(2), 368 (2010)
  23. Zhang Y, Wada T, Wang L, Sasabe H, Chem. Mater., 9, 2798 (1997)
  24. Barrett C, Choudhury B, Natansohn A, Rochon P, Macromolecules, 31(15), 4845 (1998)
  25. Kim HC, Kim JS, Kim KS, Park HK, Baek S, Ree M, J. Polym. Sci. A: Polym. Chem., 42(4), 825 (2004)
  26. Grigalevicius S, Grazulevicius JV, Gaidelis V, Jankauskas V, Polymer, 43(9), 2603 (2002)
  27. Grigoras M, Antonoaia NC, Eur. Polym. J., 41, 1079 (2005)
  28. Wong WY, Ho CL, Coord. Chem. Rev., 253, 1709 (2009)
  29. Qu JQ, Shiotsuki M, Kobayashi N, Sanda F, Masuda T, Polymer, 48(22), 6481 (2007)
  30. Wong WY, Ho CL, Gao ZQ, Mi BX, Chen CH, Cheah KW, Lin Z, Angew. Chem. Int. Ed., 45, 7800 (2006)
  31. Wong WY, Lu GL, Choi KH, Shi JX, Macromolecules, 35(9), 3506 (2002)
  32. Zhang ZB, Fujiki M, Tang HZ, Motonaga M, Torimitsu K, Macromolecules, 35(6), 1988 (2002)
  33. Wong WY, Liu L, Cui DM, Leung LM, Kwong CF, Lee TH, Ng HF, Macromolecules, 38(12), 4970 (2005)
  34. Lin Y, Chen ZK, Ye TL, Dai YF, Ma DG, Ma Z, Liu QD, Chen Y, Polymer, 51(6), 1270 (2010)
  35. Ho CL, Wong WY, Gao ZQ, Chen CH, Cheah KW, Yao B, Xie ZY, Wang Q, Ma DG, Wang LA, Yu XM, Kwok HS, Lin ZY, Adv. Funct. Mater., 18(2), 319 (2008)
  36. Moon IK, Choi CS, Kim N, Polymer, 48(12), 3461 (2007)
  37. Mori T, Kijima M, Eur. Polym. J., 45, 1149 (2009)
  38. Ghaemy M, Alizadeh R, Behmadi H, Eur. Polym. J., 45, 3108 (2009)
  39. Aly SM, Ho CL, Wong WY, Fortin D, Harvey PD, Macromolecules, 42(18), 6902 (2009)
  40. Liou GS, Hsiao SH, Huang NK, Yang YL, Macromolecules, 39(16), 5337 (2006)
  41. Liou GS, Chen HW, Yen HJ, J. Polym. Sci. A: Polym. Chem., 44(13), 4108 (2006)
  42. Van Krevelen DW, Hoftyzer PJ, Properties of Polymers, 3rd ed., Elsevier Scientic Publishing, Amsterdam (1976)
  43. Liou GS, Chang CW, Macromolecules, 41(5), 1667 (2008)