Bisquinolones as chiral fluorophores - A combined experimental and computational study of absorption and emission characteristics

Journal of Molecular Structure

Volumn 929, Issue 1-3, 2009, Pages 85-96

  Uray, Georg ^a   Kelterer, Anne Marie ^b   Hashim, Jamshed ^a   Glasnov, Toma N ^a   Oliver Kappe, C ^a   Fabian, Walter M F ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

BINAP; Carbostyril; Enantiomer; Fluorescence; TDDFT

Indexed keywords

ABSORPTION AND EMISSION SPECTRA; BINAP; BINAPHTHALENES; BLUE SHIFT; CARBOSTYRIL; CHIRAL FLUOROPHORES; COMPUTATIONAL STUDIES; CROSS-COUPLING PROTOCOL; DIPHENYLPHOSPHINE; ELECTRONIC SPECTRUM; EMISSION CHARACTERISTICS; EMISSION MAXIMA; EPSILON VALUE; ETHER LINKAGES; EXPERIMENTAL DATA; FLUORESCENCE QUANTUM YIELD; FUNCTIONALIZED; HOMOCOUPLING; ONE POT; RED SHIFT; RED-SHIFTED EMISSION; SEPARATION FACTORS; STOKE'S SHIFT; SUBSTITUTION PATTERNS; TDDFT; TIME-DEPENDENT DENSITY;

ABSORPTION; CHIRALITY; CROWN ETHERS; ENANTIOMERS; ETHERS; FLUORESCENCE; PALLADIUM; QUANTUM YIELD;

EMISSION SPECTROSCOPY;

EID: 67349240919     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2009.04.009     Document Type: Article

References (71)

1. Zheng G., Guo Y.-M., and Li W.-H. J. Am. Chem. Soc. 129 (2007) 10616-10617
2. Feuster E.K., and Glass T.E. J. Am. Chem. Soc. 125 (2003) 16174-16175
3. Diamandis E.P. Analyst 117 (1992) 1879-1884
4. Badalassi F., Klein G., Crotti P., and Reymond J.-L. Eur. J. Org. Chem. (2004) 2557-2566
5. Trenor S.R., Shultz A.R., Love B.J., and Long T.E. Chem. Rev. 104 (2004) 3059-3078
6. Schiedel M.-S., Briehn C.A., and Bauerle P. Angew. Chem. Int. Ed. 40 (2001) 4677-4680
7. Kozlov M., Bergendahl V., Burgess R., Goldfarb A., and Mustaev A. Anal. Biochem. 342 (2005) 206-213
8. Ge P., and Selvin P.R. Bioconjug. Chem. 19 (2008) 1105-1111
9. D.J. Williams, M. Gilmore, L. Steward, M. Verhagen, K.R. Aoki, US Patent 2006, 2006063221.
10. Wang J.K.T., Portbury S., Thomas M.B., Barney S., Ricca D.J., Morris D.L., Warner D.S., and Lo D.C. Proc. Natl. Acad. Sci. USA 103 (2006) 10461-10466
11. Rivera S.A., and Hudson B.S. J. Am. Chem. Soc. 128 (2006) 18-19
12. J.S. Choi, J.M. Chung, D.H. Kim, J.H. Lee, J.H. Park, Jpn. Kokai Tokyo Koho (Samsung Electronics Co. Ltd.) JP 2006, 2006171767.
13. K. Vogel, PCT Int. Appl. (Invitrogen Corporation USA) WO 2005 2005026730.
14. Rabito C.A., Chen Y., Schomacker K.T., and Modell M.D. Appl. Opt. 44 (2005) 5956-5965
15. K.K. Iu, Y.-H. Tsao, (Hewlett-Packard Development Company L.P. USA) EP Patent 2004, 1413613.
16. Chen Y., and Lehrer S.S. Biochemistry 43 (2004) 11491-11499
17. Strohmeier G.A., Fabian W.M.F., and Uray G. Helv. Chim. Acta 87 (2004) 215-226
18. Uray G., Niederreiter K.S., Belaj F., and Fabian W.M.F. Helv. Chim. Acta 82 (1999) 1408-1417
19. Fabian W.M.F., Niederreiter K.S., Uray G., and Stadlbauer W. J. Mol. Struct. 477 (1999) 209-220
20. Piszczek G., Maliwal B.P., Gryczynski I., Dattelbaum J., and Lakowicz J.R. J. Fluoresc. 11 (2001) 101-107
21. Badgujar N.S., Pazicky M., Traar P., Terec A., Uray G., and Stadlbauer W. Eur. J. Org. Chem. (2006) 2715-2722
22. Ahvale A.B., Prokopcová H., Šefcovicová J., Steinschifter W., Täubl A.E., Uray G., and Stadlbauer W. Eur. J. Org. Chem. (2008) 563-571
23. Turel M., Cajlaković M., Austin E., Dakin J.P., Uray G., and Lobnik A. Sensors Actuators B 131 (2008) 247-253
24. Panichayupakaranant P., Noguchi H., and De-Eknamkul W. Planta Med. 64 (1998) 774-775
25. Hashim J., Glasnov T.N., Kremsner J.M., and Kappe C.O. J. Org. Chem. 71 (2006) 1707-1710
26. Hashim J., and Kappe C.O. Adv. Synth. Catal. 349 (2007) 2353-2360
27. E. Ziegler, CIBA-Geigy A.-G. Patent DE 2104825
28. Ziegler E., Mittelbach H., and Steiger W. Monatsh. Chem. 101 (1970) 1059-1067
29. Fabian W. Z. Naturforsch. B 33 (1978) 332-335
30. Miyashita A., Yasuda A., Takaya H., Toriumi K., Ito T., Souchi T., and Noyori R. J. Am. Chem. Soc. 102 (1980) 7932-7934
31. Arshad N., Hashim J., and Kappe C.O. J. Org. Chem. 73 (2008) 4755-4758
32. Uray G., Badgujar N.S., Kovackova S., and Stadlbauer W. J. Heterocycl. Chem. 45 (2008) 165-172
33. Glasnov T.N., Stadlbauer W., and Kappe C.O. J. Org. Chem. 70 (2005) 3864-3870
34. Glasnov T.N., and Kappe C.O. QSAR Comb. Sci. 26 (2007) 1261-1265
35. Massue J., Bellec N., Guerro M., Bergamini J.-F., Hapiot P., and Lorcy D. J. Org. Chem. 72 (2007) 4655-4662
36. Hegmann T., Neumann B., Wolf R., and Tschierske C. J. Mater. Chem. 15 (2005) 1025-1034
37. An H., Bradshaw J.S., and Izatt R.M. Chem. Rev. 92 (1992) 543-572
38. Christensen J.J., Hill J.O., and Izatt R.M. Science 174 (1971) 459-467
39. Cram D.J., and Cram J.M. Acc. Chem. Res. 11 (1978) 8-14
40. Izatt R.M., Bradshaw J.S., Nielsen S.A., Lamb J.D., Christensen J.J., and Sen D. Chem. Rev. 85 (1985) 271-339
41. Ghosh S., Petrin M., Maki A.H., and Sousa L.R. J. Chem. Phys. 87 (1987) 4315-4323
42. Davidson R.B., Bradshaw J.S., Jones B.A., Dalley N.K., Christensen J.J., Izatt R.M., Morin F.G., and Grant D.M. J. Org. Chem. 49 (1984) 353-357
43. Peng X.-X., Lu H.-Y., Han T., and Chen C.-F. Org. Lett. 9 (2007) 895-898
44. Aoki S., Kawatani H., Goto T., Kimura E., and Shiro M. J. Am. Chem. Soc. 123 (2001) 1123-1132
45. Yapar G., and Erk C. Dyes Pigm. 48 (2001) 173-177
46. Zhao W., and Bian W. J. Mol. Struct. (THEOCHEM) 818 (2007) 43-49
47. Kurashige Y., Nakajima T., Kurashige S., Hirao K., and Nishikitani Y. J. Phys. Chem. A 111 (2007) 5544-5548
48. Jacquemin D., Perpete E.A., Assfeld X., Scalmani G., Frisch M.J., and Adamo C. Chem. Phys. Lett. 438 (2007) 208-212
49. Allen B.D., Benniston A.C., Harriman A., Llarena I., and Sams C.A. J. Phys. Chem. A 111 (2007) 2641-2649
50. Maier N.M., Uray G., Kleidernigg O., and Lindner W. Chirality 6 (1994) 116-128
51. Bauernschmitt R., and Ahlrichs R. Chem. Phys. Lett. 256 (1996) 454-464
52. Furche F., and Ahlrichs R. J. Chem. Phys. 121 (2004) 12772-12773
53. Te Velde G., Bickelhaupt F.M., Baerends E.J., Fonseca Guerra C., Van Gisbergen S.J.A., Snijders J.G., and Ziegler T. J. Comput. Chem. 22 (2001) 931-967
54. Autschbach J., and Ziegler T. J. Chem. Phys. 116 (2002) 891-896
55. Becke A.D. J. Chem. Phys. 98 (1993) 5648-5652
56. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785-789
57. Burke K., Perdew J.P., and Wang Y. In: Dobson J.F., Vignale G., and Das M.P. (Eds). Electronic Density Functional Theory: Recent Progress and New Directions (1998), Plenum
58. Perdew J.P., Burke K., and Ernzerhof M. Phys. Rev. Lett. 77 (1996) 3865-3868
59. Ernzerhof M., and Scuseria G.E. J. Chem. Phys. 110 (1999) 5029-5036
60. Becke A.D. Phys. Rev. A 38 (1988) 3098-3100
61. Perdew J.P. Phys. Rev. B 33 (1986) 8822-8824
62. Hariharan P.C., and Pople J.A. Theor. Chim. Acta 28 (1973) 213-222
63. Schäfer A., Horn H., and Ahlrichs R. J. Chem. Phys. 97 (1992) 2571-2577
64. Schäfer A., Huber C., and Ahlrichs R. J. Chem. Phys. 100 (1994) 5829-5835
65. Dewar M.J.S., Zoebisch E.G., Healy E.F., and Stewart J.J.P. J. Am. Chem. Soc. 107 (1985) 3902-3909
66. Tomasi J., Mennucci B., and Cances E. J. Mol. Struct. (THEOCHEM) 464 (1999) 211-226
67. Ampac 8 ©, 1999-2004, Semichem Inc., P.O. Box 1649 Shawnee, KS 66222, USA.
68. Ahlrichs R., Bär M., Häser M., Horn H., and Kölmel C. Chem. Phys. Lett. 162 (1989) 165-169
69. Gaussian 03, Revision B.04: M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.J.A. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian Inc., Wallingford, CT, 2004.
70. Schaftenaar G., and Noordik J.H. J. Comput. Aided Mol. Des. 14 (2000) 123-134
71. P. Flükiger, H. P. Lüthi, S. Portmann, J. Weber, MOLEKEL 4.3 Swiss National Supercomputing Centre CSCS, Manno, Switzerland, 2000-2002.