Photophysical and density functional studies of the interaction of a flavone derivative with the halides

Journal of Physical Chemistry B

Volumn 111, Issue 25, 2007, Pages 7027-7033

  Sarkar, Moloy ^a   Samanta, Anunay ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CONCENTRATION (PROCESS); HALIDE MINERALS; IONS; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS (CHEMICAL);

EMISSION BAND; FLAVONE DERIVATIVE; FLUORESCENT MOLECULAR SYSTEM; LONG-WAVELENGTH ABSORPTION;

DENSITY FUNCTIONAL THEORY;

EID: 34547330826     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0716177     Document Type: Article

References (74)

1. (a) Sengupta, P. K.; Kasha, M. Chem. Phys. Lett. 1979, 68, 382.
2. (a) Klopffer, W. Adv. Photochem. 1977, 10, 311.
3. (b) Huppert, D.; Gutman, M.; Kaufmann, M. J. Adv. Chem. Phys. 1981, 47, 643.
4. (c) Kasha, M. J. J. Chem. Soc., Faraday Trans. 2 1986, 82, 2379.
5. (d) Barbara, P. F.; Walsh, P. K.; Brus, L. E. J. Phys. Chem. 1989, 93, 29.
6. (e) Special issue: Spectroscopy and Dynamics of Elementary Proton Transfer in Polyatomic Systems. Chem. Phys. (Barbara, P. F., Trommsdorff, H. D., Eds.) 1989, 136, 153-360.
7. (f) Special Issue: M. Kasha Festschrift. J. Phys. Chem. 1991, 95, 10220-10524.
8. (a) McMorrow, D.; Kasha, M. J. Am. Chem. Soc. 1983, 105, 5133.
9. (b) McMorrow, D.; Kasha, M. J. Phys. Chem. 1984, 88, 2235.
10. (c) Bader, A. N.; Pivovarenko, V.; Demchenko, A. P.; Ariese, F.; Gooijer, C. Spectrochim. Acta, Part A 2003, 59, 1593.
11. (a) Chattopadhyay, N.; Barroso, M.; Serpa, C.; Arnaut, L. G.; Formosinho, S. J. Chem. Phys. Lett. 2004, 387, 258.
12. (b) Chattopadhyay, N.; Barroso, M.; Serpa, C.; Silva, M. I.; Arnaut, L. G.; Formosinho, S. J. Chem. Phys. Lett. 2004, 387, 263.
13. Dennison, S. M.; Guharay, J.; Sengupta, P. K. Spectrochim. Acta, Part A 1999, 55, 903.
14. (a) Strandjord, A. J. G.; Barbara, P. F. J. Phys. Chem. 1985, 89, 2355.
15. (b) Samanta, A.; Mandal, P. K. J. Phys. Chem. A 2003, 107, 6334.
16. (c) Klymchenko, A. S.; Pivovarenko, V. G.; Demchenko, A. P. J. Phys. Chem. A 2003, 107, 4211.
17. (a) Woolfe, G. J.; Thistlethwaite, P. J. J. Am. Chem. Soc. 1981, 103, 6916.
18. (b) Itoh, M.; Tokumura, K.; Tanimoto, Y.; Okada, Y.; Takeuchi, H.; Obi, K.; Tanaka, I. J. Am. Chem. Soc. 1982, 104, 4146.
19. (c) Oncul, S.; Demchenko, A. P. Spectrochim. Acta, Part A 2006, 65, 179.
20. (a) Ameer-Beg, S.; Ormson, S. M.; Brown, R. G.; Matousek, P.; Towrie, M.; Nibbering, E. T. J.; Foggi, P.; Neuwahl, F. V. R. J. Phys. Chem. A 2001, 105, 3709.
21. (b) Shynkar, V. V.; Mély, Y.; Duportail, G.; Piémont, E.; Klymchenko, A. S.; Demchenko, A. P. J. Phys. Chem. A 2003, 107, 9522.
22. (c) Ameer-Beg, S.; Ormson, S. M.; Poteau, X.; Brown, R. G.; Foggi, P.; Bussotti, L.; Neuwahl, F. V. R. J. Phys. Chem. A 2004, 108, 6938.
23. (a) Chou, P. T.; Huang, C. H.; Pu, S. C.; Cheng, Y. M.; Liu, Y. H.; Wang, Y.; Chen, C. T. J. Phys. Chem. A 2004, 108, 6452.
24. (b) Chou, P. T.; Pu, S. C.; Cheng, Y. M.; Yu, W. S.; Yu, Y. C.; Hung, F. T.; Hu, W. P. J. Phys. Chem. A 2005, 109, 3777.
25. (a) Klymchenko, A. S.; Demchenko, A. P. Phys. Chem. Chem. Phys. 2003, 5, 461.
26. (b) Ercelen, S.; Klymchenko, A. S.; Demchenko, A. P. Anal. Chim. Acta 2002, 464, 273.
27. (a) Klymchenko, A. S.; Duportail, G.; Ozturk, T.; Pivovarenko, V. G.; Mély, Y.; Demchenko, A. P. Chem. Biol. 2002, 9, 1199.
28. (b) Shynkar, V. V.; Klymchenko, A. S.; Duportail, G.; Demchenko, A. P.; Mély, Y. Biochem. Biophys. Acta 2005, 1712, 128.
29. Lü, F.; Gao, L.; Fang, Y. Prog. Chem. 2005, 17, 773.
30. Tasdemir, D.; Kaiser, M.; Brun, R.; Yardley, V.; Schmidt, T. J.; Tosun, F.; Rüedi, P. Antimicrob. Agents Chemother. 2006, 50, 1352.
31. Mishra, L.; Sing, A. K.; Trigun, S. K.; Sing, S. K.; Pandey, S. M. Indian J. Exp. Biol. 2004, 42, 660.
32. (a) Poteau, X.; Saroja, G.; Spies, C.; Brown, R. G. J. Photochem. Photobiol. A: Chem. 2004, 162, 431.
33. (b) Binbuga, N.; Henry, W. P.; Schultz, T. P. Polyhedron 2007, 26, 6.
34. (a) Reigel's Handbook of Industrial Chemistry, 9th ed.; Kent, J. A., Ed.; Van Nostrand Reinhold-International Thomson Publishing: New York, 1992.
35. (b) Mason, C. F. Biology of Freshwater Pollution, 2nd ed.; Longman: New York, 1991.
36. (c) Spichiger-Keller, U. E. Chemical Sensors and Biosensors for Medical and Biological Applications; Wiley-VCH: Weinheim, Germany, 1998.
37. (a) Kirk, K. L. Biochemistry of the Halogens and Inorganic Halides; Plenum Press: New York, 1991; p 58.
38. (b) Kleerekoper, M. Endocrinol. Metab. Clin. North Am. 1998, 27, 441.
39. Wiseman, A. Handbook of Experimental Pharmacology XX/2, Part 2; Springer-Verlag: Berlin, 1970; pp 48-97.
40. Amendola, V.; Esteban-Gomez, D.; Fabbrizzi, L.; Lecchelli, M. Acc. Chem. Res. 2006, 39, 343.
41. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals; Pergamon Press: New York, 1980.
42. (a) Meyer, N. D.; Haemers, A.; Mishra, L.; Pandey, H.; Pieters, L. A. C.; Dirk, A.; Berghe, V.; Vlietinck, A. J. J. Med. Chem. 1991, 34, 736.
43. (b) Ormson, S. M.; Brown, R. G.; Vollmer, F.; Rettig, W. J. Photochem. Photobiol. A: Chem. 1994, 81, 65.
44. Sarkar, M.; Samanta, A. Synthesis 2006, 20, 3425.
45. (a) Becke, D. A. J. Chem. Phys. 1993, 98, 5648.
46. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
47. (a) Ghosh, T.; Maiya, B. G.; Wong, M. W. J. Phys. Chem. A 2004, 108, 11249.
48. (b) Jose, D. A.; Kumar, D. K.; Ganguly, B.; Das, A. Org. Lett. 2004, 6, 3445.
49. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
50. Messerschmidt, M.; Wagner, A.; Wong, M. W.; Luger, P. J. Am. Chem. Soc. 2002, 124, 732.
51. (a) Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454.
52. (b) Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. J. Chem. Phys. 1998, 108, 4439.
53. Wong, M. W.; Frish, M. J.; Weiberg, K. B. J. Am. Chem. Soc. 1991, 113, 4776.
54. Cossi, M.; Barone, V. J. Chem. Phys. 2000, 112, 2427.
55. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
56. Cho, E. J.; Moon, J. W.; Ko, S. W.; Lee, J. Y.; Kim, S. K.; Yoon, J.; Nam, K. C. J. Am. Chem. Soc. 2003, 125, 12376.
57. The fluorescence profile of the new band is characterized by single exponential decay with a lifetime of ∼285 ps.
58. (a) Recent examples of luminescent anion sensing include the following: Kim, K. N.; Singhi J.; Kim, S. J.; Kim, H. G.; Kim, J. K.; Lee, L. W.; Kim, K. S.; Yoon, J. A. 2003, 54, 2083.
59. (b) Cho, E. J.; Ryu, B. J.; Lee, Y. J.; Nam, K. C. Org. Lett. 2005, 7, 2607.
60. (c) Kim, K.; Yoon, J. T. Chem. Commun. 2002, 770.
61. (d) de Silva, A. P.; McClean, G. D.; Pagliari, S. Chem. Commun. 2003, 2010.
62. (e) Jose, D. A.; Kumar, D. K.; Ganguly, B.; Das, A. Tetrahedron Lett. 2005, 46, 5343.
63. (f) Gunnlaugsson, T.; Glynn, M.; Tocci (née Hussey), G. M.; Kruger, P. E.; Pfeffer, F. M. Coord. Chem. Rev. 2006, 250, 3094.
64. (a) Xu, G.; Tarr, M. A. Chem. Commun. 2004, 1050.
65. (b) Kovalchuk, A.; Bricks, J. L.; Reck, G.; Rurack, K.; Schulz, B.; Szumna, A.; Weisshoff, H. Chem. Commun. 2004, 1946.
66. (a) Taki, M.; Wolford, J. L.; O'Halloran, T. V. J. Am. Chem. Soc. 2004, 126, 712.
67. (b) Yang, R.; Li, K.; Wang, K.; Zhao, F.; Li, N.; Liu, F. Anal. Chem. 2003, 75, 612.
68. (c) Yang, R.; Chan, W.; Lee, A. W. M.; Xia, P.; Zhang, H.; Li, K. J. Am. Chem. Soc. 2003, 125, 2884.
69. (d) Maruyama, S.; Kikuchi, K.; Hirano, T.; Urano, Y.; Nagano, T. J. Am. Chem. Soc. 2002, 124, 10650.
70. (e) Tong, H.; Wang, L.; Jing, X. X. B.; Wang, F.; Macromolecules 2002, 35, 7169.
71. (f) Banthia, S.; Samanta, A. J. Phys. Chem. B 2006, 110, 6437.
72. (a) Liu, B.; Tian, H. J. Mater. Chem. 2005, 15, 2681.
73. (b) Coskun, A.; Akkaya, E. Tetrahedron Lett. 2004, 45, 4947.
74. Brooks, S. J.; Evans, L. S.; Gale, P. A.; Hursthouse, M. B. Chem. Commun. 2004, 734.