Ortho-substituent effect on fluorescence and electroluminescence of arylamino-substituted coumarin and stilbene

Organic Letters

Volumn 5, Issue 8, 2003, Pages 1261-1264

  Chen, Chao Tsen ^a   Chiang, Chih Long ^b   Lin, Yu Chung ^a   Chan, Li Hsin ^b   Huang, Chien Huang ^a   Tsai, Zong Wei ^b   Chen, Chin Ti ^b  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

COUMARIN DERIVATIVE; STILBENE DERIVATIVE;

ARTICLE; COLOR; FILM; FLUORESCENCE; LUMINESCENCE; QUANTUM CHEMISTRY; SOLID; SYNTHESIS;

EID: 0141628925     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034268h     Document Type: Article

References (43)

1. Krasovitskii, B. M.; Bolotin, B. M. Organic Luminescent Materials; Vopian, V. G., Translator; VCH: Weinheim, Germany, 1988.
2. Valeur, B. Molecular Fluorescence; Wiley-VCH: Weinheim, Germany, 2002.
3. (a) Rademacher, A.; Märkle, S.; Langhals, H. Chem. Ber. 1982, 115, 2927.
4. (b) Bohnen, A.; Koch, K.-H.; Lüttke, W.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1990, 29, 525.
5. (c) Geerts, Y.; Quante, H.; Platz, H.; Mahrt, R.; Hopmeier, M.; Böhm, A.; Müllen, K. J. Mater. Chem. 1998, 8, 2357.
6. (d) Chen, C. H.; Tang, C. W.; Shi, J.; Klubek, K. P. Thin Solid Films 2000, 363, 327.
7. (e) Langhals, H.; Ismael, R.; Yürük, O. Tetrahedron 2000, 56, 5435.
8. (f) Chen, C. H.; Tang, C. W. Appl. Phys. Lett. 2001, 79, 3711.
9. (g) Chan, L.-H.; Yeh, H.-C.; Chen, C.-T. Adv. Mater. 2001, 13, 1637.
10. (a) Gensch, T.; Hofkens, J.; Heirmann, A.; Tsuda, K.; Verheijen, W.; Vosch, T.; Christ, T.; Basché T.; Müllen, K.; De Schryver, F. C. Angew. Chem., Int. Ed. 1999, 38, 3752.
11. (b) Satayesh, S.; Grimsdale, A. C.; Weil, T.; Enkelmann, V.; Müllen, K.; Meghdadi, F.; List, E. J. W.; Leising, G. J. Am. Chem. Soc. 2001, 123, 946.
12. (c) Pogantsch, A.; Wenzl, F. P.; List, E. J. W.; Leising, G.; Grimsdale, A. C.; Müllen, K. Adv. Mater. 2002, 14, 1061.
13. (a) Bettenhausen, J.; Strohriegl, P. Adv. Mater. 1996, 8, 507.
14. (b) Katsuma, K.; Shirota, Y. Adv. Mater. 1998, 10, 223.
15. (c) Halim, M.; Pillow, J. N. G.; Samuel, I. D. W.; Burn, P. L. Adv. Mater. 1999, 11, 371.
16. (d) Lupon, J. M.; Hemingway, L. R.; Samuel, I. D. W.; Burn, P. L. J. Mater. Chem. 2000, 10, 867.
17. (e) Freeman, A. W.; Koene, S. C.; Malenfant, P. R. L.; Thompson, M. E.; Fréchet, J. M. J. J. Am. Chem. Soc. 2000, 122, 12385.
18. (f) Wang, S.; Oldham, W. J., Jr.; Hudack, R. A.; Bazan, G. C. J. Am. Chem. Soc. 2000, 122, 5695.
19. (g) Yeh, H.-C.; Lee, R.-H.; Chan, L.-H.; Lin, T.-Y. J.; Chen, C.-T.; Balasubramaniam, B.; Tao, Y.-T. Chem. Mater. 2001, 13, 2788.
20. (h) Ostrowski, J. C.; Robinson, M. R.; Heeger, A. J.; Bazan, G. C. Chem. Commun 2002, 784.
21. For reviews, see: (a) Shirota, Y. J. Mater. Chem. 2000, 10, 1. (b) Thelakkat, M. Macromol. Mater. Chem. Eng. 2002, 287, 442
22. For reviews, see: (a) Shirota, Y. J. Mater. Chem. 2000, 10, 1. (b) Thelakkat, M. Macromol. Mater. Chem. Eng. 2002, 287, 442
23. Jones, G., II; Jackson, W. R.; Choi, C.-Y.; Bergmark, W. R. J. Phys. Chem. 1985, 89, 294.
24. (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
25. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
26. For recent examples, see: (a) Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (b) Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (c) Watanabe, M.; Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 2000, 41, 481. (d) Harris, M. C.; Buchwald, S. L. J. Org. Chem. 2000, 65, 5327. (e) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Chem. Commun. 2000, 133.
27. For recent examples, see: (a) Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (b) Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (c) Watanabe, M.; Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 2000, 41, 481. (d) Harris, M. C.; Buchwald, S. L. J. Org. Chem. 2000, 65, 5327. (e) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Chem. Commun. 2000, 133.
28. For recent examples, see: (a) Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (b) Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (c) Watanabe, M.; Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 2000, 41, 481. (d) Harris, M. C.; Buchwald, S. L. J. Org. Chem. 2000, 65, 5327. (e) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Chem. Commun. 2000, 133.
29. For recent examples, see: (a) Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (b) Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (c) Watanabe, M.; Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 2000, 41, 481. (d) Harris, M. C.; Buchwald, S. L. J. Org. Chem. 2000, 65, 5327. (e) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Chem. Commun. 2000, 133.
30. For recent examples, see: (a) Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (b) Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (c) Watanabe, M.; Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 2000, 41, 481. (d) Harris, M. C.; Buchwald, S. L. J. Org. Chem. 2000, 65, 5327. (e) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Chem. Commun. 2000, 133.
31. (a) Goodbrand, H. B.; Hu, N.-X. J. Org. Chem. 1999, 64, 670.
32. (b) Bacon, R. G. R.; Hill, H. A. O. Chem. Rev. 1965, 19, 95.
33. (c) Bushby, R. J.; McGill, D. R.; Ng, K. M.; Taylor, N. J. Mater. Chem. 1997, 7, 2343.
34. (d) Gauthier, S.; Frechet, J. M. J.; Synthesis, 1987, 383.
35. (a) Rettig, W. Angew. Chem., Int. Ed. Engl. 1986, 25, 971.
36. (b) Rettig, W.; Vogel, M.; Drexhage, K. H.; Sens, R. Chem. Phys. Lett. 1988, 147, 452.
37. f values of XTPS and TTPS are not unexpected. Arylamino-substituted stilbene fluorophores bearing sterically hindered ortho substituents have a higher chance of going through trans-cis isomerization at the photoexcited state and hence exhibit weaker fluorescence intensity than those without an ortho substituent. Yang, J.-S.; Chiou, S.-Y.; Liau, K.-L. J. Am. Chem. Soc. 2002, 124, 2518.
38. TPBI here denotes 2,2′,2″ -(1,3,5-phenylene)tris(1-phenyl-1H-benzimidazole) and NPB is 1,4-bis(1-naphylphenylamino)biphenyl. ITO is an indium-tin oxide-coated glass. The fabrication and characterization of the devices follow a similar procedure to that reported by Chan et al.: Chan, L.-H.; Lee, R.-H.; Hsieh, C.-F.; Yeh, H.-C.; Chen, C.-T. J. Am. Chem. Soc. 2002, 124, 6469.
39. coupling is possibly as high as 2-fold in previous estimations. (a) Chen, H. Y.; Lam, W. Y.; Luo, J. D.; Ho, Y. L.; Tang, B. Z.; Zhu, D. B. Appl. Phys. Lett. 2002, 81, 574. (b) Patel, N. K.; Cina, S.; Burroughes, J. H. IEEE J. Sel. Top. Quantum Electron. 2002, 8, 346.
40. coupling is possibly as high as 2-fold in previous estimations. (a) Chen, H. Y.; Lam, W. Y.; Luo, J. D.; Ho, Y. L.; Tang, B. Z.; Zhu, D. B. Appl. Phys. Lett. 2002, 81, 574. (b) Patel, N. K.; Cina, S.; Burroughes, J. H. IEEE J. Sel. Top. Quantum Electron. 2002, 8, 346.
41. (a) Li, Y.; Fung, M. K.; Xie, Z.; Lee, S.-T.; Hung, L.-S.; Shi, J. Adv. Mater. 2002, 14, 1317.
42. (b) Shih, H.-T.; Lin, C.-H.; Shih, H.-H.; Cheng, C.-H. Adv. Mater. 2002, 14, 1409.
43. (c) Kim, Y.-H.; Shin, D.-C.; Kim, S.-H.; Ko, C.-H.; Yu, H.-S.; Chae, Y.-S.; Kwon, S.-K. Adv. Mater. 2002, 14, 1690.