Synthesis, X-ray crystal structures, and solid-state fluorescence properties of 5,5-dialkyl-9-dibutylamino-5H-benzo[b]naphtho[1,2-d]furan-6-one and 3,3-dialkyl-9-dibutylamino-3H-benzo[kl]xanthen-2-one

European Journal of Organic Chemistry

Volumn , Issue 18, 2008, Pages 3085-3094

  Ooyama, Yousuke ^a   Hayashi, Akiko ^a   Okamoto, Tomohiro ^a   Egawa, Haruka ^a   Mamura, Toshiki ^a   Yoshida, Katsuhira ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

Crystal structure; Dyes pigments; Fluorescence; Oxygen heterocycles; Substituent effects

Indexed keywords

EID: 53749094937     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800219     Document Type: Article

References (62)

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) K. Hirano, S. Minakata, M. Komatsu, Chem. Lett. 2001, 8-9;
20. b) Y. Sonoda, Y. Kawanishi, T. Ikeda, M. Goto, S. Hayashi, N. Tanigaki, K. Yase, J. Phys. Chem. B 2003, 107, 3376-3383;
21. c) R. Davis, S. Abraham, N. P. Rath, S. Das, New J. Chem. 2004, 28, 1368-1372;
22. d) V. de Halleux, J.-P. Calbert, P. Brocorens, J. Cornil, J.-P. Declercq, J.-L. Brédas, Y. Geerts, Adv. Funct. Mater. 2004, 14, 649-659;
23. e) 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;
24. f) E. Horiguchi, S. Matsumoto, K. Funabiki, M. Matsui, Bull. Chem. Soc. Jpn. 2005, 78, 1167-1173;
25. g) S. Mizukami, H. Houjou, K. Sugaya, E. Koyama, H. Tokuhisa, T. Sasaki, M. Kanesato, Chem. Mater. 2005, 17, 50-56;
26. h) Y. Mizobe, N. Tohnai, M. Miyata, Y. Hasegawa, Chem. Commun. 2005, 1839-1841;
27. i) I. Vayá, M. C. Jiménez, M. Miranda, Tetrahedron: Asymmetry 2005, 16, 2167-2171;
28. j) Z. Xie, B. Yang, L. Liu, M. li, D. Lin, Y. Ma, G. Cheng, S. Liu, J. Phys. Org. Chem. 2005, 18, 962-973;
29. k) Y. Ooyama, Y. Harima, Chem. Lett. 2006, 902-903;
30. l) Y. Ooyama, Y. Kagawa, Y. Harima, Eur. J. Org. Chem. 2007, 3613-3621.
31. a) K. Yoshida, Y. Ooyama, M. Miyazaki, S. Watanabe, J. Chem. Soc. Perkin Trans. 2 2002, 700-707;
32. b) Y. Ooyama, T. Nakamura, K. Yoshida, New J. Chem. 2005, 29, 447-456;
33. c) Y. Ooyama, T. Okamoto, T. Yamaguchi, T. Suzuki, A. Hayashi, K. Yoshida, Chem. Eur. J. 2006, 12, 7827-7838;
34. d) Y. Ooyama, T. Mamura, K. Yoshida, Tetrahedron Lett. 2007, 48, 5791-5793;
35. e) Y. Ooyama, T. Mamura, K. Yoshida, Eur. J. Org. Chem. 2007, 30, 5010-5019.
36. a) K. Yoshida, J. Yamazaki, Y. Tagashira, S. Watanabe, Chem. Lett. 1996, 9-10;
37. b) K. Yoshida, T. Tachikawa, J. Yamasaki, S. Watanabe, S. Tokita, Chem. Lett. 1996, 1027-1028;
38. c) K. Yoshida, H. Miyazaki, Y. Miura, Y. Ooyama, S. Watanabe, Chem. Lett. 1999, 837-838;
39. d) K. Yoshida, Y. Ooyama, S. Tanikawa, S. Watanabe, Chem. Lett. 2000, 714-715;
40. e) K. Yoshida, Y. Ooyama, S. Tanikawa, S. Watanabe, J. Chem. Soc. Perkin Trans. 2 2002, 708-714;
41. f) Y. Ooyama, K. Yoshida, New J. Chem. 2005, 29, 12041212.
42. H. Langhals, T. Potrawa, H. Nöth, G. Linti, Angew. Chem. 1989, 101, 497-499;
43. Angew. Chem. Int. Ed. Engl. 1989, 28, 478-480.
44. K. Yoshida, K. Uwada, H. Kumaoka, L. Bu, S. Watanabe, Chem. Lett. 2001, 808-809.
45. C.-H. Zhao, A. Wakamiya, Y. Inukai, S. Yamaguchi, J. Am. Chem. Soc. 2006, 128, 15934-15935.
46. H. Langhals, R. Ismael, O. Yürük, Tetrahedron 2000, 56, 5435-5441.
47. J. N. Moorthy, P. Natarajan, P. Venkatakrishnan, D.-F. Huang, T. J. Chow, Org. Lett. 2007, 9, 5215-5218.
48. Y. Li, F. Li, H. Zhang, Z. Xie, W. Xie, H. Xu, B. Li, F. Shen, L. Ye, M. Hanif, D. Ma, Y. Ma, Chem. Commun. 2007, 231-233.
49. K. Kalyanasundaram, J. K. Thomas, J. Phys. Chem. 1977, 81, 2176-2180.
50. B. Valeur, Molecular Fluorescence, VCH, Weinheim, 2002.
51. T. Yoshihara, H. Shimada, H. Shizuka, S. Tobita, Phys. Chem. Chem. Phys. 2001, 3, 4972-4978.
52. K.-Y. Chen, Y.-M. Cheng, C.-H. Lai, C.-C. Hsu, M.-L. Ho, G.-H. Lee, P.-T. Chou, J. Am. Chem. Soc. 2007, 129, 4534-4535.
53. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909.
54. a) J. E. Ridley, M. C. Zerner, Theor. Chim. Acta 1973, 32, 111-134;
55. b) J. E. Ridley, M. C. Zerner, Theor. Chim. Acta 1976, 42, 223-236;
56. c) A. D. Bacon, M. C. Zerner, Theor. Chim. Acta 1979, 53, 21-54.
57. a) M. Adachi, Y. Murata, S. Nakamura, J. Org. Chem. 1993, 58, 5238-5244;
58. b) W. M. F. Fabian, S. Schuppler, O. S. Wolfbeis, J. Chem. Soc. Perkin Trans. 2 1996, 853-856.
59. C. A. Heller, R. A. Henry, B. A. Mclaughlin, D. E. Bills, J. Chem. Eng. Data 1974, 19, 214-219.
60. teXsan: Crystal Structure Analysis Package, Molecular Structure Corporation, 1985 and 1992.
61. A. Altomare, M. C. Burla, M. Camalli, M. Cascarano, C. Giacovazzo, A. Guagliardi, G. Polidori, J. Appl. Crystallogr. 1994, 27, 435.
62. 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.