Synthesis, X-ray crystal structures and solid-state fluorescence properties of 3-dibutylamino-6-alkoxy-6-phenylnaphtho[2,3-b]benzofuran-11(6H)-one derivatives

European Journal of Organic Chemistry

Volumn , Issue 30, 2007, Pages 5010-5019

  Ooyama, Yousuke ^a   Mamura, Toshiki ^a   Yoshida, Katsuhira ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

Crystal structures ; Fluorescent dyes; Interaction; Solid state fluorescence; Substituent effects

Indexed keywords

EID: 35548954662     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700484     Document Type: Article

References (54)

1. a) C. W. Tang, S. A. VansSlyke, Appl. Phys. Lett. 1987, 51, 913-915;
2. b) C. W. Tang, S. A. VansSlyke, C. H. Chen, J. Appl. Phys. 1989, 65, 3610-3616;
3. c) J. Schi, C. W. Tang, Appl. Phys. Lett. 1997, 70, 1665-1667;
4. d) A. Kraft, A. C. Grimsdale, A. B. Holmes, Angew. Chem. 1998, 110, 416-443;
5. Angew. Chem. Int. Ed. 1998, 37, 402-428;
6. e) U. Mitschke, P. Bäuerle, J. Mater. Chem. 2000, 10, 1471-1507;
7. f) K.-C. Wong, Y.-Y. Chien, R.-T. Chen, C.-F. Wang, Y.-T. Liu, H.-H. Chiang, P.-Y. Hsieh, C.-C. Wu, C. H. Chou, Y. O. Su, G.-H. Lee, S.-M. Peng, J. Am. Chem. Soc. 2002, 124, 11576-11577;
8. g) C. J. Tonzola, M. M. Alam, W. K. Kaminsky, S. A. Jenekhe, J. Am. Chem. Soc. 2003, 125, 13548-13558;
9. h) H.-C. Yeh, L.-H. Chan, W.-C. Wu, C.-T. Chen, J. Mater. Chem. 2004, 14, 1293-1298;
10. i) C.-T. Chen, Chem. Mater. 2004, 16, 4389-4400;
11. j) C.-L. Chiang, M.-F. Wu, D.-C. Dai, Y.-S. Wen, J.-K. Wang, C.-T. Chen, Adv. Funct. Mater. 2005, 15, 231-238;
12. k) D. Berner, C. Klein, M. D. Nazeeruddin, F. de Angelis, M. Castellani, P. Bugnon, R. Scopelliti, L. Zuppiroli, M. Graetzel, J. Mater. Chem. 2006, 16, 4468-4474.
13. a) Z.-S. Wang, F.-Y. Li, C.-H. Hang, L. Wang, M. Wei, L.-P. Jin, N.-Q. Li, J. Phys. Chem. B 2000, 104, 9676-9682;
14. b) A. Ehret, L. Stuhl, M. T. Spitler, J. Phys. Chem. B 2001, 105, 9960-9965;
15. c) K. Hara, T. Sato, R. Katoh, A. Furube, Y. Ohga, A. Shinpo, S. Suga, K. Sayama, H. Sugihara, H. Arakawa, J. Phys. Chem. B 2003, 107, 597-606;
16. d) K. R. J. Thomas, J. T. Kin, Y.-C. Hsu, K.-C. Ho, Chem. Commun. 2005, 4098-4100;
17. e) D. P. Hagberg, T. Edvinsson, T. Marinado, G. Boschloo, A. Hagfeld, L. Sun, Chem. Commun. 2006, 2245-2247;
18. f) S.-L. Li, K.-J. Jiang, K.-F. Shao, L.-M. Yang, Chem. Commun. 2006, 2792-2794.
19. a) R. Davis, S. Abraham, N. P. Rath, S. Das, New J. Chem. 2004, 28, 1368-1372;
20. b) E. Horiguchi, S. Matsumoto, K. Funabiki, M. Matsui, Bull. Chem. Soc. Jpn. 2005, 78, 1167-1173.
21. a) Y. Ooyama, T. Nakamura, K. Yoshida, New J. Chem. 2005, 29, 447-456;
22. b) Y. Ooyama, T. Okamoto, T. Yamaguchi, T. Suzuki, A. Hayashi, K. Yoshida, Chem. Eur. J. 2006, 7827-7838;
23. c) Y. Ooyama, S. Yoshikawa, S. Watanabe, K. Yoshida, Org. Biomol. Chem. 2006, 4, 3406-3409;
24. d) Y. Ooyama, S. Yoshikawa, S. Watanabe, K. Yoshida, Org. Biomol. Chem. 2007, 5, 1260-1269.
25. H.-C. Yeh, W.-C. Wu, Y.-S. Wen, D.-C. Dai, J.-K. Wang, C.-T. Chen, J. Org. Chem. 2004, 69, 6455-6462.
26. K. Yoshida, Y. Ooyama, H. Miyazaki, S. Watanabe, J. Chem. Soc. Perkin Trans. 2 2002, 700-707.
27. S. Nakatsuji, H. Nakazumi, H. Fukuma, T. Yahiro, K. Nakashima, M. Iyoda, S. Akiyama, J. Chem. Soc. Perkin Trans. 1 1991, 1881.
28. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909.
29. a) J. E. Ridley, M. C. Zerner, Theor. Chim. Acta 1973, 32, 111-134;
30. b) J. E. Ridley, M. C. Zerner, Theor. Chim. Acta 1976, 42, 223-236;
31. c) A. D. Bacon, M. C. Zerner, Theor. Chim. Acta 1979, 53, 21-54.
32. a) M. Adachi, Y. Murata, S. Nakamura, J. Org. Chem. 1993, 58, 5238-5244;
33. b) W. M. F. Fabian, S. Schuppler, O. S. Wolfbeis, J. Chem. Soc. Perkin Trans. 2 1996, 853-856.
34. a) Z. Fei, N. Kocher, C. J. Mohrschladt, H. Ihmels, D. Stalke, Angew. Chem. 2003, 115, 807-811;
35. Angew. Chem. Int. Ed. 2003, 42, 783-787;
36. b) J. L. Scott, T. Yamada, K. Tanaka, New J. Chem. 2004, 28, 447-450.
37. a) K. Yoshida, J. Yamazaki, Y. Tagashira, S. Watanabe, Chem. Lett. 1996, 9-10;
38. b) K. Yoshida, T. Tachikawa, J. Yamasaki, S. Watanabe, S. Tokita, Chem. Lett. 1996, 1027-1028;
39. c) K. Yoshida, H. Miyazaki, Y. Miura, Y. Ooyama, S. Watanabe, Chem. Lett. 1999, 837-838;
40. d) K. Yoshida, Y. Ooyama, S. Tanikawa, S. Watanabe, Chem. Lett. 2000, 714-715;
41. e) K. Yoshida, Y. Ooyama, S. Tanikawa, S. Watanabe, J. Chem. Soc. Perkin Trans. 2 2002, 708-714;
42. f) Y. Ooyama, K. Yoshida, New J. Chem. 2005, 29, 1204-1212.
43. H. Langhals, T. Potrawa, H. Nöth, G. Linti, Angew. Chem. 1989, 101, 497-499;
44. Angew. Chem. Int. Ed. Engl. 1989, 28, 478-480.
45. A. Dreuw, J. Plötner, L. Lorenz, J. Wachtveitl, J. E. Djanhan, J. Brüning, T. Metz, M. Bolte, M. U. Schmidt, Angew. Chem. 2005, 117, 7961-7964;
46. Angew. Chem. Int. Ed. 2005, 44, 7783-7786.
47. K. Yoshida, K. Uwada, H. Kumaoka, L. Bu, S. Watanabe, Chem. Lett. 2001, 808-809.
48. Y. Ooyama, Y. Harima, Chem. Lett. 2006, 902-903.
49. C. A. Heller, R. A. Henry, B. A. McLaughlin, D. E. Bills, J. Chem. Eng. Data. 1974, 19, 214-219.
50. teXsan: Crystal Structure Analysis Package, Molecular Structure Corporation 1985 and 1992.
51. M. C. Burla, M. Camalli, G. Cascaeano, C. Giacovazzo, G. Polidori, R. Spagna, D. Viterbo, J. Appl. Crystallogr. 1989, 22, 389-393.
52. DIRDIF94. P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, R. de Gelder, R. Israel, J. M. M. Smits, The DIRIF94 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1994.
53. Hai-Fu Fan, Structure Analysis Programs with Intelligent Control, Rigaku Corporation, Tokyo, Japan, 1991.
54. A. Altomare, M. C. Burla, M. Camalli, M. Cascarano, C. Giacovazzo, A. Guagliardi, G. Polidori, J. Appl. Crystallogr. 1994, 27, 435.