Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Crystal Structures and Luminescence Properties of Pd(II) and Pt(II) Complexes with 2,5-Bis(thiophene)-1-nonyl-3,4-bis(methylthio)pyrrole

  • Kang, Jun-Gill (Department of Chemistry, Chungnam National University) ;
  • Oh, Sung-Il (Department of Chemistry, Chungnam National University) ;
  • Cho, Dong-Hee (Department of Chemistry, Chungnam National University) ;
  • Nah, Min-Kook (Department of Chemistry, Chungnam National University) ;
  • Park, Chang-Moon (Department of Chemistry, Chungnam National University) ;
  • Bae, Young-Ju (Department of Chemistry, Kwangwoon University) ;
  • Woo, Tack-Han (Department of Chemistry, Kwangwoon University) ;
  • Park, Young-Jin (Department of Chemistry, Kwangwoon University) ;
  • Lee, Sang-Woo (Department of Chemistry, Kwangwoon University) ;
  • Kim, In-Tae (Department of Chemistry, Kwangwoon University)
  • Published : 2009.05.20
Download PDF
⟨ Previous Next ⟩

Abstract

Complexes of Pd(btnbmtp)$Cl_2$ and Pt(btnbmptp)$Cl_2$ (btnbmtp = 2,5-bis(thiophen)-1-nonyl-3,4-bis(methylthio)- pyrrole) were prepared and their crystal structures were determined at room temperature. In the structures, the two thiophene moieties lie in cis form with an average dihedral angle of $55.26^{\circ}$ to the pyrrole frame. The luminescence properties of the free ligand and the complexes were investigated in solution and solid states. The luminescence of the compounds were not favored by substituting thiophene moieties to the pyrrole frame, compared to the unsubstituted nbmptp (nbmptp = 1-nonyl-3,4-bis(methylthio)pyrrole). In particular, thiophene substitution quenched the emission from the complexes dissolved in ,$CH_2Cl_2$ and reduced the charge transfer transitions from S atoms of the thio moieties to Pt in crystalline state, which was very characteristic of Pt(nbmptp)$Cl_2$.

Keywords

References

  1. Nielsen, C. B.; Angerhofer, A.; Abboud, K. A.; Reynolds, J. R. J. Am. Chem. Soc. 2008, 130, 9734 https://doi.org/10.1021/ja7112273
  2. Ma, C.; Taya, M.; Xu, C. Electrochim. Acta 2008, 54, 598 https://doi.org/10.1016/j.electacta.2008.07.049
  3. Johansson, T.; Mammo, W.; Svensson, M.; Andersson, M. R.; Inganas, O. Chem. Mater. 1999, 11, 3133 https://doi.org/10.1021/cm991052u
  4. Egbe, D. A. M.; Nguyen, Le. H.; Muehlbacher, D.; Hoppe, H.; Schmidtke, K.; Sariciftci, N. S. Thin Solid Films 2006, 511, 486 https://doi.org/10.1016/j.tsf.2005.12.090
  5. Zhou, E.; Tan, Z.; Huo, L.; He, Y.; Yang, C.; Li, Y. J. Phys. Chem. B 2006, 110, 26062 https://doi.org/10.1021/jp065442x
  6. Sergawie, A.; Admassie, S.; Mammo, W.; Yohannes, T.; Solomon, T. Syn. Metals 2008, 158, 307 https://doi.org/10.1016/j.synthmet.2007.11.012
  7. Li, G.; Jiang, K.-J.; Li, Y.-F.; Li, S.-L.; Yang, L.-M. J. Phys. Chem. C 2008, 112, 11591 https://doi.org/10.1021/jp802436v
  8. Brabec, C. J.; Winder, C.; Sariciftci, N. S.; Hummelen, J. C.; Dhanabalan, A.; Van Hal, P. A.; Janssen, R. A. J. Adv. Funct. Mater. 2002, 12, 709 https://doi.org/10.1002/1616-3028(20021016)12:10<709::AID-ADFM709>3.0.CO;2-N
  9. Hissler, M.; Lescop, C.; Reau, R. Pure Appl. Chem. 2005, 77, 2099 https://doi.org/10.1351/pac200577122099
  10. Kuo, W.-J.; Chen, Y.-H.; Jeng, R.-J.; Chan, L.-H.; Lin, W.-P.; Yang, Z.-M. Tetrahedron 2007, 63, 7086 https://doi.org/10.1016/j.tet.2007.05.032
  11. Wu, S.-H.; Huang, H.-M.; Chen, K.-C.; Hu, C.-W.; Hsu, C.-C.; Tsiang, R. C.-C. Adv. Funct. Mater. 2006, 16, 1959 https://doi.org/10.1002/adfm.200500604
  12. Hobbs, M. G.; Baumgartner, T. Eur. J. Inorg. Chem. 2007, 3611
  13. Kuila, B. K.; Garai, A.; Nandi, A. K. Chem. Mater. 2007, 19, 5443 https://doi.org/10.1021/cm7020214
  14. Cheylan, S.; Bolink, H. J.; Fraleoni-Morgera, A.; Puigdollers, J.; Voz, C.; Mencarelli, I.; Setti, L.; Alcubilla, R.; Badenes, G. Org. Electronics 2007, 8, 641 https://doi.org/10.1016/j.orgel.2007.04.009
  15. Qi, Z.-J.; Feng, W.-D.; Sun, Y.-M.; Yan, D.-Z.; He, Y.-F.; Yu, J. J. Mater. Sci.: Mater. Electronics 2007, 18, 869 https://doi.org/10.1007/s10854-007-9149-0
  16. Matsushima, T.; Adachi, C. Chem. Mater. 2008, 20, 2881 https://doi.org/10.1021/cm800098f
  17. Zhou, Q.; Li, C. M.; Li, J.; Cui, X.; Gervasio, D. J. Phys. Chem. C 2007, 111, 11216 https://doi.org/10.1021/jp072390i
  18. Henderson, J. C.; Kiya, Y.; Hutchison, G. R.; Abruna, H. D. J. Phys. Chem. C 2008, 112, 3989 https://doi.org/10.1021/jp076774k
  19. Rudge, A.; Raistrick, I.; Gottesfeld, S.; Ferraris, J. P. Electrochim. Acta 1994, 39, 273 https://doi.org/10.1016/0013-4686(94)80063-4
  20. Henderson, J. C.; Kiya, Y.; Hutchison, G. R.; Abruna, H. D. J. Phys. Chem. C 2008, 112, 3989 https://doi.org/10.1021/jp076774k
  21. Guernion, N. J. L.; Hayes, W. Curr. Org. Chem. 2004, 8, 637 https://doi.org/10.2174/1385272043370771
  22. Li, H.; Lambert, C.; Stahl, R. Macromol. 2006, 39, 2049 https://doi.org/10.1021/ma0601868
  23. Goldoni, F.; Antolini, L.; Pourtois, G.; Schenning, A. P. H. J.; Janssen, R. A. J.; Lazzaroni, R.: Brédas, J.-L.; Meijer, E. W. Eur. J. Inorg. Chem. 2001, 821
  24. Matthews, J. R.; Goldoni, F.; Kooijman, H.; Spek, A. L.; Schenning, A. P. H. J.; Meijer, E. W. Macromol. Rapid Comm. 2007, 28, 1809 https://doi.org/10.1002/marc.200700399
  25. Kang, J.-G.; Cho, D.-H.; Park, C.; Kang, S. K.; Kim, I. T.; Lee, S. W.; Lee, H. H.; Lee, Y. N.; Lim, D. W.; Lee, S. J.; Kim, S. H.; Bae, Y. J. Bull. Korean Chem. Soc. 2008, 29, 599 https://doi.org/10.5012/bkcs.2008.29.3.599
  26. Kang, J.-G.; Cho, H.-K.; Park, C.; Kang, S. K.; Kim, I. T.; Lee, S. W.; Lee, H. H.; Lee, Y. N.; Cho, S. H.; Lee, J. H.; Lee, S. H. Bull. Korean Chem. Soc. 2008, 29, 679 https://doi.org/10.5012/bkcs.2008.29.3.679
  27. Richards, J. J.; Melander, C. J. Org. Chem. 2008, 73, 5191 https://doi.org/10.1021/jo800618q
  28. Sheldrick, G. M. Program SADABS; Area-detector absorption correction University of Gottingen: Gottingen, Germany, 1996
  29. SHELXTL, 5.030 ed.; Brucker Analytical X-ray Instruments, Inc.: Madison, WI, 1998
  30. Sheldrick, G. M. SHELXS-97, SHELXL-97, Programs for Crystal Structure Analysis; University of Gottingen: Gottingen, Germany, 1997
  31. Kang, J.-G.; Cho, H.-G.; Kang, S. K.; Park, C.; Lee, S. W.; Park, G. B.; Lee, J. S.; Kim, I. T. J. Photochem. Photobio. A : Chem. 2006, 183, 212 https://doi.org/10.1016/j.jphotochem.2006.03.023

Cited by

  1. N-substituted 2,5-di(2-thienyl)pyrroles: application, production, properties, and electrochemical polymerization (review) vol.47, pp.2, 2011, https://doi.org/10.1007/s10593-011-0735-y
  2. }methylpalladium(II) dichloromethane hemisolvate vol.66, pp.6, 2010, https://doi.org/10.1107/S1600536810017824