DOI QR코드

DOI QR Code

Structure and Luminescence Properties of Poly(1-hexyl-3,4-dimethyl-2,5-pyrrolylene)

  • Kang, Jun-Gill (Department of Chemistry, Chungnam National University) ;
  • Kim, Tack-Jin (Department of Chemistry, Chungnam National University) ;
  • Park, Chang-Moon (Department of Chemistry, Chungnam National University) ;
  • Woo, Lee-Sang (Department of Chemistry, Kwangwoon University) ;
  • Kim, In-Tae (Department of Chemistry, Kwangwoon University)
  • 발행 : 2004.05.20

초록

A poly(1-hexyl-3,4-dimethyl-2,5-pyrrolylene) (PHDP) was prepared and its luminescence in tetrahydrofuran (THF) was studied. When PHDP is excited by UV light, it produces very strong blue luminescence. The quantum yield of PHDP (Q = 36.9%) is much greater than that of the monomer, 1-hexyl-3,4-dimethylpyrrole (HDP) with Q = 0.61%. The principal luminescence of PHDP has a single decay component with ca. 1 ns, whereas the decay of HDP is complicated. The molecular structure and conformational behavior of HDP and the oligomers up to trimer have been also determined by ab initio Hartree-Fock (HF/6-31$G^{**}$), density functional theory (DFT-B3LYP/6-31$G^{**}$), and semiempirical (ZINDO) methods. According to the results of calculations, it is proposed that the enhanced quantum yield of the polymer PHDP results mostly from the ${\pi}$-conjugation between neighboring pyrrole rings.

키워드

참고문헌

  1. Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, R.N.; Mackay, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B. Nature(London) 1990, 347, 539. https://doi.org/10.1038/347539a0
  2. Gao, J.; Heeger, A. J.; Lee, J. Y.; Kim, C. Y. Synth. Met. 1996, 82, 221. https://doi.org/10.1016/S0379-6779(96)03794-0
  3. An, B.-K.; Kim, Y.-H.; Shin, D.-C.; Park, S. Y.; Yu, H.-S.; Kwon, S.-K. Macromol. 2001, 34, 3993. https://doi.org/10.1021/ma0016735
  4. Clery, D. Science 1994, 263, 1700. https://doi.org/10.1126/science.263.5154.1700
  5. Zheng, M.; Bai, F.; Li,Y.; Yu, G.; Yang, C.; Zhu, D. Synth. Met. 1999, 102, 1275. https://doi.org/10.1016/S0379-6779(98)01474-X
  6. Lee, D. W.; Kwon, K.-Y.; Jin, J.-L.; Park, Y.; Kim, Y.-R.; Hwang, I.-W.Chem. Mater. 2001, 13, 565. https://doi.org/10.1021/cm000794g
  7. Kittlesen, G. P.; White, H. S.; Wrighton, M. S. J. Am. Chem. Soc.1984, 106, 7389. https://doi.org/10.1021/ja00336a016
  8. Kudoh, Y.; Tsuchiya, S.; Kojima, T.; Fukuyama, M.;Yoshimura, S. Synth. Met. 1991, 41/43, 1133.
  9. Krings, L. H. M.; Havinga, E. E.; Donkers, J. J. T. M.; Vork, F. T. A. Synth. Met. 1993, 54, 453. https://doi.org/10.1016/0379-6779(93)91091-F
  10. Smela, E.; Inganas, O.; Lundstrom, I. Science 1995, 268, 1735. https://doi.org/10.1126/science.268.5218.1735
  11. Kunugi, Y.; Nigorikawa, K.; Harima, Y.; Yamashita, K. Chem.Commun. 1994, 873.
  12. Charlestworth, J. M.; Partridge, A. C.;Carrard, N. J. Phys. Chem. 1993, 97, 5418. https://doi.org/10.1021/j100122a038
  13. Kim, I. T.; Elsenbaumer, R. L. Chem. Commun. 1998, 327.
  14. Kim, I. T.; Elsenbaumer, R. L. Macromol. 2000, 33, 6407. https://doi.org/10.1021/ma9907643
  15. Kim, I. T.; Lee, S. W.; Kwak, T. H.; Lee, J. Y.; Park, H. S.; Kim, S.Y.; Lee, C. M.; Jung, H. E.; Kang, J.-G.; Kim, T.-J.; Kang, H.-J.;Park, C. Macrol. Rapid Commun. 2002, 23, 551. https://doi.org/10.1002/1521-3927(20020601)23:9<551::AID-MARC551>3.0.CO;2-#
  16. Brocks, G.; Kelly, P. J.; Car, R. Synth. Mat. 1993, 57, 4243. https://doi.org/10.1016/0379-6779(93)90731-B
  17. Millefiopi, S.; Alparone, A. J. Chem. Soc. Faraday Trans. 1998,94, 25. https://doi.org/10.1039/a705780f
  18. Brocks, G.; Tol, A. Synth. Mat. 1999, 101, 516. https://doi.org/10.1016/S0379-6779(98)01416-7
  19. Choi, J.; Chipara, M.; Xu, B.; Yang, C. S.; Doudin, B.; Dowben, P. A. Chem. Phys. Lett. 2001, 343, 193. https://doi.org/10.1016/S0009-2614(01)00469-9
  20. Jaguar 3.5; Schrodinger, Inc.: Portland, Oregon, 1998.
  21. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.;Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery,J. A. Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J.M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.;Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.;Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G.A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck,A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.;Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.;Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.;Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong,M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle,E. S.; Pople, J. A.; Gaussian 98, Revision A.9; Gaussian, Inc.:Pittsburgh, PA, 1998.
  22. de Mello, J. C.; Wittmann, H. F.; Friend, R. H. Adv. Mater. 1997, 9, 230. https://doi.org/10.1002/adma.19970090308
  23. Kim, K.-B.; Kim, Y.-I.; Chun, H.-G.; Cho, T.-Y.;Jung, J.-S.; Kang, J.-G. Chem. Mater. 2002, 14, 5045. https://doi.org/10.1021/cm020592f
  24. McGehee, M. D.; Bergstedt, T. B.; Zhang, C.; Saab, A. P.; O'Regan, M. B.; Bazan, G. C.; Srdanov, V. I.; Heeger, A. J. Adv. Mater. 1999, 11, 1349. https://doi.org/10.1002/(SICI)1521-4095(199911)11:16<1349::AID-ADMA1349>3.0.CO;2-W
  25. Johnson, G. E. J. Chem. Phys. 1975, 62, 4697. https://doi.org/10.1063/1.430418
  26. Kido, J.; Shionya, H.; Nagai, K. Appl. Phys. Lett. 1995, 67, 2281. https://doi.org/10.1063/1.115126
  27. Gettinger, C. L.; Heeger, A. J.; Drake, J. M.; Pine, D. J. J. Chem.Phys. 1994, 101, 1673. https://doi.org/10.1063/1.468438
  28. Nguyen, T.-Q.; Doan, V.; Schwartz, B. J. J. Chem. Phys. 1999,110, 8.
  29. Theander, M.; Svensson, M.; Ruseckas, A.; Zigmantase, D.;Sundström, V.; Andersson, A. R.; Inganäs, O. Chem. Phys. Lett.2001, 337, 277. https://doi.org/10.1016/S0009-2614(01)00208-1

피인용 문헌

  1. Synthesis of 5,6-Dihydro[1,10]phenanthroline Derivatives and Their Properties as Hole-Blocking Layer Materials for Phosphorescent Organic Light-Emitting Diodes vol.26, pp.10, 2004, https://doi.org/10.5012/bkcs.2005.26.10.1569
  2. Chemical Vapor Deposition Polymerization of Poly(arylenevinylene)s and Applications to Nanoscience vol.27, pp.2, 2004, https://doi.org/10.5012/bkcs.2006.27.2.169
  3. Optical and Conformational Studies on (o-Tolyl)3PAuCl vol.27, pp.2, 2004, https://doi.org/10.5012/bkcs.2006.27.2.299
  4. Physical Chemistry Research Articles Published in the Bulletin of the Korean Chemical Society: 2003-2007 vol.29, pp.2, 2008, https://doi.org/10.5012/bkcs.2008.29.2.450
  5. X-ray Crystal Structure and Luminescence Properties of Pd(II) and Pt(II) Complexes with Dithiopyrrole vol.29, pp.3, 2004, https://doi.org/10.5012/bkcs.2008.29.3.599
  6. Structural and Optical Properties of a Pd(II) Complex with 1-Nonyl-3,4-bis(methylthio)pyrrole vol.29, pp.3, 2004, https://doi.org/10.5012/bkcs.2008.29.3.679
  7. Structural and Optical Properties of a Pd(II) Complex with 1-Nonyl-3,4-bis(methylthio)pyrrole vol.29, pp.3, 2004, https://doi.org/10.5012/bkcs.2008.29.3.679