Design of near-infrared dyes based on π-conjugation system extension. Theoretical evaluation of arylimidazole derivatives of perylene chromophore

Chemistry of Materials

Volumn 11, Issue 8, 1999, Pages 2107-2114

  Adachi, Masafumi ^a   Nagao, Yukinori ^a,b  

^a MITSUBISHI CHEMICAL CORPORATION   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000078798     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm990051z     Document Type: Article

References (55)

1. (a) Daehne, S., Resch-Genger, U., Wolfbeis, O. S., Eds. Near-Infrared Dyes for High Technology Applications; Kluwer Academic Publishers: Dordrecht, 1998.
2. (b) Fabian, J.; Nakazumi, H.; Matsuoka, M. Chem. Rev. 1992, 92, 1197.
3. (c) Law, K.-Y. Chem. Rev. 1993, 93, 449.
4. (d) Peng, Z.; Geise, H. J. Bull. Soc. Chim. Belg. 1996, 105, 739.
5. (e) Burkinshaw, S. M.; Hallas, G.; Towns, A. D. Rev. Prog. Color. Relat. Top. 1996, 26, 47.
6. Leznoff, C. C., Lever, A. B. P., Eds. Phthalocyanines Properties and Applications; VCH: New York, 1989, 1993, 1993, 1996; Vols. 1-4.
7. (a) Rademacher, A.; Mä rkle, S.; Langhals, H. Chem. Ber. 1982, 115, 2927.
8. (b) Langhals, H. Chem. Ber. 1985, 118, 4641.
9. (c) Demmig, S.; Langhals, H. Chem. Ber. 1988, 121, 225.
10. (d) Ebeid, El-Z. M.; El- Daly, S. A.; Langhals, H. J. Phys. Chem. 1988, 92, 4565.
11. (e) Langhals, H.; Fünfschilling, J.; Glatz, D.; Zschokke- Gränacher, I. Spectrochim. Acta 1988, 44A, 311.
12. (f) Langhals, H.; Demmig, S.; Huber, H. Spectrochim. Acta 1988, 44A, 1189.
13. (g) Kaiser, H.; Lindner, J.; Langhals, H. Chem. Ber. 1991, 124, 529.
14. (h) Johansson, L. B.-A.; Langhals, H. Spectrochim. Acta 1991, 47A, 857.
15. (i) Deligeorgiev, T.; Zaneva, D.; Petkov, I.; Timcheva, Il.; Sabnis, R. Dyes Pigm. 1994, 24, 75.
16. (j) Adachi, M.; Murata, Y.; Nakamura, S. J. Phys. Chem. 1995, 99, 14240.
17. (k) Mercadante, R.; Trsic, M.; Duff, J.; Aroca, R. J. Mol. Struct. (THEOCHEM) 1997, 394, 215.
18. (a) Krasovitskii, B. M.; Bolotin, B. M. Organic Luminescent Materials; VCH: Weinheim, 1988.
19. (b) Herbst, W.; Hunger, K. Industrial Organic Pigments, 2nd ed.; VCH: Weinheim, 1997.
20. (c) Popovic, Z. D.; Loutfy, R. O.; Hor, Ah-M. Can. J. Chem. 1985, 63, 134.
21. (d) Panayotatos, P.; Parikh, D.; Sauers, R.; Bird, G.; Piechowski, A.; Husain, S. Solar Cells 1986, 18, 71.
22. (e) Seybold, G.; Wagenblast, G. Dyes Pigm. 1989, 11, 303.
23. (f) Sadrai, M.; Hadel, L.; Sauers, R. R.; Husain, S.; Krogh-Jespersen, K.; Westbrook, J. D.; Bird, G. R. J. Phys. Chem. 1992, 96, 7988.
24. (a) Klebe, G.; Graser, F.; Hädicke, E.; Berndt, J. Acta Crystallogr. 1989, B45, 69.
25. (b) McKerrow, A. J.; Buncel, E.; Kazmaier, P. M. Can. J. Chem. 1993, 71, 390.
26. (c) Kazmaier, P. M.; Hoffmann, R. J. Am. Chem. Soc. 1994, 116, 9684.
27. (d) Erk, P.; Hetzenegger, J.; Böhm, A. Eur. Coat. J. 1997, 906.
28. (a) Orchin, M.; Jaffé, H. H. Symmetry, Orbitals, and Spectra; Wiley-Interscience: New York, 1971.
29. (b) Griffiths, J. Colour and Constitution of Organic Molecules; Academic Press: London, 1976.
30. (c) Fabian, J.; Hartmann, H. Light Absorption of Organic Colorants; Springer-Verlag: Berlin, 1980.
31. (d) Zollinger, H. Color Chemistry, 2nd ed.; VCH: Weinheim, 1991.
32. (a) Luká c, I.; Langhals, H. Chem. Ber. 1983, 116, 3524.
33. (b) Popovic, Z. D.; Hor, Ah-M.; Loutfy, R. O. Chem. Phys. 1988, 127, 451.
34. (c) Loutfy, R. O.; Hor, A. M.; Kazmaier, P.; Tam, M. J. Imag. Sci. 1989, 33, 151.
35. (d) Fujita, Y.; Adachi, C.; Tsutsui, T.; Saito, S. Nippon Kagaku Kaishi 1992, 1154.
36. (e) Quante, H.; Geerts, Y.; Müllen, K. Chem. Mater. 1997, 9, 495.
37. (a) Nagao, Y.; Ishikawa, N.; Tanabe, Y.; Misono, T. Chem. Lett. 1979, 151.
38. (b) Nagao, Y.; Ishikawa, N.; Tanabe, Y.; Misono, T. Nippon Kagaku Kaishi 1980, 1391.
39. (c) Nagao, Y.; Misono, T. Dyes Pigm. 1984, 5, 171.
40. Langhals, H.; Sprenger, S.; Brandherm, M.-T. Liebigs Ann. 1995, 481.
41. (a) Désilets, D.; Kazmaier, P. M.; Burt, R. A. Can. J. Chem. 1995, 73, 319.
42. (b) Désilets, D.; Kazmaier, P. M.; Burt, R. A.; Hamer, G. K. Can. J. Chem. 1995, 73, 325.
43. (c) Quante, H.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 1323.
44. (d) Langhals, H.; Schönmann, G.; Feiler, L. Tetrahedron Lett. 1995, 36, 6423.
45. (e) Holtrup, F. O.; Müller, G. R. J.; Quante, H.; De Feyter, S.; De Schryver, F. C.; Müllen, K. Chem. Eur. J. 1997, 3, 219.
46. (f) Rohr, U.; Schlichting, P.; Böhm, A.; Gross, M.; Meerholz, K.; Bräuchle, C.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1998, 37, 1434.
47. (g) Geerts, Y.; Quante, H.; Platz, H.; Mahrt, R.; Hopmeier, M.; Böhm, A.; Müllen, K. J. Mater. Chem. 1998, 8, 2357.
48. (a) Ridley, J.; Zerner, M. Theor. Chim. Acta 1973, 32, 111.
49. (b) Ridley, J. E.; Zerner, M. C. Theor. Chim. Acta 1976, 42, 223.
50. (c) Bacon, A. D.; Zerner, M. C. Theor. Chim. Acta 1979, 53, 21.
51. (d) Zerner, M. C.; Loew, G. H.; Kirchner, R. F.; Mueller-Westerhoff, U. T. J. Am. Chem. Soc. 1980, 102, 589.
52. (a) Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
53. (b) MOPAC Ver. 5, Stewart, J. J. P. QCPE Bull. 1989, 9, 10.
54. (a) Nishimoto, K.; Mataga, N. Z. Phys. Chem. (Neue Folge) 1957, 12, 335.
55. (b) Mataga, N.; Nishimoto, K. Z. Phys. Chem. (Neue Folge) 1957, 13, 140.