Long-wavelength-absorbing and -emitting carbostyrils with high fluorescence quantum yields

Helvetica Chimica Acta

Volumn 82, Issue 9, 1999, Pages 1408-1417

  Uray, Georg ^a   Niederreiter, Karlheinz S ^a   Belaj, Ferdinand ^a   Fabian, Walter M F ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

6,7 DIMETHOXY 1 METHYL 3 NITRO 4 (TRIFLUOROMETHYL)QUINOLIN 2 (1H) ONE; CARBOSTYRIL DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CALCULATION; CRYSTAL STRUCTURE; DATA ANALYSIS; FLUORESCENCE; LIGHT ABSORPTION; LUMINESCENCE; PH; PREDICTION;

EID: 0032876141     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1522-2675(19990908)82:9<1408::AID-HLCA1408>3.0.CO;2-Q     Document Type: Article

References (42)

1. W. M. F. Fabian, K. S. Niederreiter, G. Uray, W. Stadlbauer, J. Mol. Struct. 1999, 477, 209.
2. M. Li, P. R. Selvin, Bioconjugate Chem. 1997, 8, 127; E. F. G. Dickson, A. Pollak, E. P. Diamandis, J. Photochem. Photobiol. B 1995, 27, 3; D. Parker, J. A. G. Williams, J. Chem. Soc., Dalton Trans. 1996, 3613; I. Hemmilä, Clin. Chem. 1985, 31, 359; A. Rieutord, P. Prognon, F. Brion, G. Mahuzier, Analyst 1997, 122, 59R; G. Jürgens, A. Hermann, D. Aktuna, W. Petek, Clin. Chem. 1992, 38, 853; C. Tzougraki, C. Noula, R. Geiger, G. Kokotos, Liebigs Ann. Chem. 1994, 365; T. Besson, B. Joseph, P. Moreau, M.-C. Viaud, G. Coudert, G. Guillaumet, Heterocycles 1992, 34, 273.
3. M. Li, P. R. Selvin, Bioconjugate Chem. 1997, 8, 127; E. F. G. Dickson, A. Pollak, E. P. Diamandis, J. Photochem. Photobiol. B 1995, 27, 3; D. Parker, J. A. G. Williams, J. Chem. Soc., Dalton Trans. 1996, 3613; I. Hemmilä, Clin. Chem. 1985, 31, 359; A. Rieutord, P. Prognon, F. Brion, G. Mahuzier, Analyst 1997, 122, 59R; G. Jürgens, A. Hermann, D. Aktuna, W. Petek, Clin. Chem. 1992, 38, 853; C. Tzougraki, C. Noula, R. Geiger, G. Kokotos, Liebigs Ann. Chem. 1994, 365; T. Besson, B. Joseph, P. Moreau, M.-C. Viaud, G. Coudert, G. Guillaumet, Heterocycles 1992, 34, 273.
4. M. Li, P. R. Selvin, Bioconjugate Chem. 1997, 8, 127; E. F. G. Dickson, A. Pollak, E. P. Diamandis, J. Photochem. Photobiol. B 1995, 27, 3; D. Parker, J. A. G. Williams, J. Chem. Soc., Dalton Trans. 1996, 3613; I. Hemmilä, Clin. Chem. 1985, 31, 359; A. Rieutord, P. Prognon, F. Brion, G. Mahuzier, Analyst 1997, 122, 59R; G. Jürgens, A. Hermann, D. Aktuna, W. Petek, Clin. Chem. 1992, 38, 853; C. Tzougraki, C. Noula, R. Geiger, G. Kokotos, Liebigs Ann. Chem. 1994, 365; T. Besson, B. Joseph, P. Moreau, M.-C. Viaud, G. Coudert, G. Guillaumet, Heterocycles 1992, 34, 273.
5. M. Li, P. R. Selvin, Bioconjugate Chem. 1997, 8, 127; E. F. G. Dickson, A. Pollak, E. P. Diamandis, J. Photochem. Photobiol. B 1995, 27, 3; D. Parker, J. A. G. Williams, J. Chem. Soc., Dalton Trans. 1996, 3613; I. Hemmilä, Clin. Chem. 1985, 31, 359; A. Rieutord, P. Prognon, F. Brion, G. Mahuzier, Analyst 1997, 122, 59R; G. Jürgens, A. Hermann, D. Aktuna, W. Petek, Clin. Chem. 1992, 38, 853; C. Tzougraki, C. Noula, R. Geiger, G. Kokotos, Liebigs Ann. Chem. 1994, 365; T. Besson, B. Joseph, P. Moreau, M.-C. Viaud, G. Coudert, G. Guillaumet, Heterocycles 1992, 34, 273.
6. M. Li, P. R. Selvin, Bioconjugate Chem. 1997, 8, 127; E. F. G. Dickson, A. Pollak, E. P. Diamandis, J. Photochem. Photobiol. B 1995, 27, 3; D. Parker, J. A. G. Williams, J. Chem. Soc., Dalton Trans. 1996, 3613; I. Hemmilä, Clin. Chem. 1985, 31, 359; A. Rieutord, P. Prognon, F. Brion, G. Mahuzier, Analyst 1997, 122, 59R; G. Jürgens, A. Hermann, D. Aktuna, W. Petek, Clin. Chem. 1992, 38, 853; C. Tzougraki, C. Noula, R. Geiger, G. Kokotos, Liebigs Ann. Chem. 1994, 365; T. Besson, B. Joseph, P. Moreau, M.-C. Viaud, G. Coudert, G. Guillaumet, Heterocycles 1992, 34, 273.
7. M. Li, P. R. Selvin, Bioconjugate Chem. 1997, 8, 127; E. F. G. Dickson, A. Pollak, E. P. Diamandis, J. Photochem. Photobiol. B 1995, 27, 3; D. Parker, J. A. G. Williams, J. Chem. Soc., Dalton Trans. 1996, 3613; I. Hemmilä, Clin. Chem. 1985, 31, 359; A. Rieutord, P. Prognon, F. Brion, G. Mahuzier, Analyst 1997, 122, 59R; G. Jürgens, A. Hermann, D. Aktuna, W. Petek, Clin. Chem. 1992, 38, 853; C. Tzougraki, C. Noula, R. Geiger, G. Kokotos, Liebigs Ann. Chem. 1994, 365; T. Besson, B. Joseph, P. Moreau, M.-C. Viaud, G. Coudert, G. Guillaumet, Heterocycles 1992, 34, 273.
8. M. Li, P. R. Selvin, Bioconjugate Chem. 1997, 8, 127; E. F. G. Dickson, A. Pollak, E. P. Diamandis, J. Photochem. Photobiol. B 1995, 27, 3; D. Parker, J. A. G. Williams, J. Chem. Soc., Dalton Trans. 1996, 3613; I. Hemmilä, Clin. Chem. 1985, 31, 359; A. Rieutord, P. Prognon, F. Brion, G. Mahuzier, Analyst 1997, 122, 59R; G. Jürgens, A. Hermann, D. Aktuna, W. Petek, Clin. Chem. 1992, 38, 853; C. Tzougraki, C. Noula, R. Geiger, G. Kokotos, Liebigs Ann. Chem. 1994, 365; T. Besson, B. Joseph, P. Moreau, M.-C. Viaud, G. Coudert, G. Guillaumet, Heterocycles 1992, 34, 273.
9. M. Li, P. R. Selvin, Bioconjugate Chem. 1997, 8, 127; E. F. G. Dickson, A. Pollak, E. P. Diamandis, J. Photochem. Photobiol. B 1995, 27, 3; D. Parker, J. A. G. Williams, J. Chem. Soc., Dalton Trans. 1996, 3613; I. Hemmilä, Clin. Chem. 1985, 31, 359; A. Rieutord, P. Prognon, F. Brion, G. Mahuzier, Analyst 1997, 122, 59R; G. Jürgens, A. Hermann, D. Aktuna, W. Petek, Clin. Chem. 1992, 38, 853; C. Tzougraki, C. Noula, R. Geiger, G. Kokotos, Liebigs Ann. Chem. 1994, 365; T. Besson, B. Joseph, P. Moreau, M.-C. Viaud, G. Coudert, G. Guillaumet, Heterocycles 1992, 34, 273.
10. Roithner Lasertechnik, Fleischmanngasse 9, A-1040 Vienna, Austria, e-mail: rlt@mcb.at.
11. W. M. F. Fabian, in 'Scifi97, Conference on Scintillating and Fiber Detectors (November 1997)', in 'AIP Conference Proceedings 450', Ed. A. D. Bross, R. C. Ruchti, M. R. Wayne, Woodbury, New York, 1998, pp. 14-24.
12. W. M. F. Fabian, in 'Scifi97, Conference on Scintillating and Fiber Detectors (November 1997)', in 'AIP Conference Proceedings 450', Ed. A. D. Bross, R. C. Ruchti, M. R. Wayne, Woodbury, New York, 1998, pp. 14-24.
13. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902; J. J. P. Stewart, J. Comput.-Aided Mol. Des. 1990, 4, 1; MOPAC 6.0, QCPE program no. 455.
14. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902; J. J. P. Stewart, J. Comput.-Aided Mol. Des. 1990, 4, 1; MOPAC 6.0, QCPE program no. 455.
15. J. E. Ridley, M. C. Zerner, Them. Chim. Acta 1973, 32, 111; ZINDO, a comprehensive semiempirical quantum chemistry package: M. C. Zerner, Quantum Theory Project, University of Florida, Gainesville, FL, USA.
16. J. E. Ridley, M. C. Zerner, Them. Chim. Acta 1973, 32, 111; ZINDO, a comprehensive semiempirical quantum chemistry package: M. C. Zerner, Quantum Theory Project, University of Florida, Gainesville, FL, USA.
17. Y. Forster, E. Haas, Anal. Biochem. 1993, 209, 9; S. Sanghi, D. Mohan, Spectrochim. Acta 1996, 52A, 1229.
18. Y. Forster, E. Haas, Anal. Biochem. 1993, 209, 9; S. Sanghi, D. Mohan, Spectrochim. Acta 1996, 52A, 1229.
19. R. Boese, D. Blaser, M. Nussbaumer, T. M. Krygowski, Struct. Chem. 1992, 3, 363.
20. M. Kido, K. Nakagawa, Chem. Pharm. Bull. 1982, 30, 1488.
21. A. Bondi, J. Phys. Chem. 1964, 68, 441.
22. F. H. Allen, J. E. Davies, J. J. Galloy, O. Johnson, O. Kennard, C. F. Macrae, E. M. Mitchell, G. F. Mitchell, J. M. Smith, D. G. Watson, J. Chem. Inf. Comput Sci. 1991, 31, 187.
23. R. J. Butcher, R. Gilardi, J. L. Flippen-Anderson, C. George, New J. Chem. (Nouv. J. Chim.) 1992, 16, 679.
24. A. L. Rheingold, C. J. Baldacchini, C. W. Grote, J. Crystallogr. Spectrosc. Res. 1989, 19, 25.
25. J. F. W. Keana, S. M. Kher, Sui Xiong Cai, C. M. Dinsmore, A. G. Glenn. J. Guastella, Jin-Cheng Huang, V. Ilyin, Yixin Lu, P. L. Mouser, R. L. Woodward, E. Weber, J. Med. Chem. 1995, 38, 4367.
26. J. M. Cense, V. Agafanov, R. Ceolin, P. Ladure, N. Rodier, Struct. Chem. 1994, 5, 79.
27. W. W. Mantulin, P.-S. Song, J. Am. Chem. Soc. 1973, 95, 5122.
28. L. Limpach, Ber. Dtsch. Chem. Ges. 1931, 970.
29. K. C. Frisch, M. T. Bogert, J. Org. Chem. 1944, 9, 338.
30. A. Steinacker Dey, M. M. Joullie, J. Heterocycl. Chem. 1965, 2, 120.
31. M. A. Alonso, M. Blanco, C. Avendano, J. C. Menendez, Heterocycles 1993, 36, 2315.
32. M. Pailer, A. Schleppnik, A. Meller, Monatsh. Chem. 1965, 96, 1695.
33. J. Roy, A. P. Bhaduri, Indian J. Chem. Sect. B 1978, 744.
34. Y. Kitahara, M. Shimizu, A. Kubo, Heterocycles 1990, 31, 2085.
35. R. Borah, N. Deka, J. C. Sarma, J. Chem. Res. Synop. 1997, 110.
36. O. A. Ponomarev, E. R. Vasina, S. N. Yarmolenko, V. G. Mitina, N. S. Pivnenko, Zh. Obshch. Khim. 1990, 60, 1161.
37. G. M. Sheldrick, SHELXS-97. Program for the Solution of Crystal Structures. University of Göttingen, Germany, 1997.
38. G. M. Sheldrick, SHELXL-97. Program for the Refinement of Crystal Structures. University of Göttingen, Germany, 1997.
39. SYBYL 6.3, Tripos Associates, St. Louis, MO, USA.
40. J. Baker, J. Comput. Chem. 1986, 7, 385.
41. M. M. Karelson, M. C. Zerner, J. Phys. Chem. 1992, 96, 6949.
42. C. K. Johnson, ORTEP. Report ORNL-3794. Oak Ridge National Laboratory, Tennessee, USA, 1965.