Comparative theoretical study of rotamerism and excited state intramolecular proton transfer of 2-(2'-Hydroxyphenyl)benzimidazole, 2-(2'-Hydroxyphenyl)imiďazo [4,5-b]pyridine, 2-(2'-Hydroxyphenyl)imidazo [4,5-c] pyridine and 8-(2'-Hydroxyphenyl)purine

Journal of Physical Chemistry A

Volumn 113, Issue 44, 2009, Pages 12063-12070

  Chipem, Francis A S ^a   Krishnamoorthy, G ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE RING; BENZIMIDAZOLES; COMPARATIVE STUDIES; CONFIGURATION INTERACTION SINGLES; EMISSION BANDS; EMISSION DATA; ENERGY DIFFERENCES; EXCITATION SPECTRUM; EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER; EXCITED-STATE PROTON TRANSFER; EXPERIMENTAL DATA; FLUORESCENCE EMISSION; FLUORESCENCE QUENCHING; NONRADIATIVE PROCESS; PHOTOPHYSICS; PROTON TRANSFER PROCESS; RADIATIVE TRANSITIONS; ROTAMERS; THEORETICAL RESULT; THEORETICAL STUDY; TIME-DEPENDENT DFT; TWISTED STATE;

BENZENE; DENSITY FUNCTIONAL THEORY; EMISSION SPECTROSCOPY; ETHERS; EXCITED STATES; FLUORESCENCE; GROUND STATE; MOLECULES; NITROGEN; POTENTIAL ENERGY; POTENTIAL ENERGY SURFACES; PROBABILITY DENSITY FUNCTION; PYRIDINE; QUANTUM CHEMISTRY; QUENCHING; SULFUR COMPOUNDS;

PROTON TRANSFER;

EID: 71049178713     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp903535g     Document Type: Article

References (55)

1. Kasha, M. J. Chem. Soc., Faraday Trans. 2 1986, 82, 2379-2392.
2. Douhal, A.; Kim, S. K.; Zewail, A. H. Nature 1995, 378, 260-263.
3. Chen, C.-L.; Lin, C-W.; Hsieh, C.-C.; Lai, C.-H.; Lee, G.-H.; Wang, C.-C.; Chou, P.-T. J. Phys. Chem. A 2009, 113, 205-214.
4. Lukeman, M.; Wan, P. J. Am. Chem. Soc. 2002, 124, 9458-9464.
5. Frey, W.; Elsaesser, T. Chem. Phys. Lett. 1992, 189, 565-570.
6. Schwartz, B. J.; Peteanu, L. A.; Harris, C. B. J. Phys. Chem. 1992, 96 3591-3598
7. Seo, J.; Kim, S.; Park, S. Y. J. Am. Chem. Soc. 2004, 126, 11154-11155.
8. Santra, S.; Krishnamoorthy, G.; Dogra, S. K. Chem. Phys. Lett. 2000, 327, 230-237.
9. Prieto, F. R.; Mosquera, M.; Novo, M. J. Phys. Chem. 1990, 94, 8536-8542.
10. Das, S. K.; Dogra, S. K. Bull. Chem. Soc. Jpn. 1997, 70, 307-313.
11. Sarkar, N.; Das, K.; Das, S.; Datta, A.; Nath, D.; Bhattacharyya, K. J. Phys. Chem. 1995, 99, 17711-17714.
12. Sytnik, A.; Kasha, M. Proc. Natl. Acad Sci. U.S.A. 1994, 91, 8627-8630.
13. Maity, S. S.; Samanta, S.; Sardar, P. S.; Pal, A.; Dasgupta, S.; Ghosh, S. Chem. Phys. 2008, 354, 162-173.
14. Douhal, A. Chem. Rev. 2004, 104, 1955-1976.
15. Roberts, E. L.; Dey, J.; Warner, I. M. J. Phys. Chem. A 1997, 101, 5296-5301.
16. Yushchenko, D. A.; Shvadchak, V. V.; Klymchenko, A. S.; Duportail, G.; Pivovarenko, V. G.; Mely, Y. J. Phys. Chem. A 2007, 111, 10435-10438.
17. Chou, P.; McMorrow, D.; Aartsma, T. J.; Kasha, M. J. Phys. Chem. 1984, 88, 4596-4599.
18. Paterson, M. J.; Robb, M. A.; Biancafort, L.; DeBellis, A. D. J. Phys. Chem. A 2005, 109, 7527-7537.
19. Nishiya, T.; Yamuchi, S.; Hirota, N.; Baba, M.; Hamazaki, I. J. Phys. Chem. 1986, 90, 5730-5735.
20. Chou, P. T.; Martinej, M. L. Radiat. Phys. Chem. 1993, 41, 373-378.
21. Zhang, G.; Wang, H.; Yu, Y.; Xiong, F.; Tang, G.; Chen, W. Appl. Phys. B: Lasers and Opt. 2003, 76, 677-681.
22. Ozturk, T.; Klymchenko, A. S.; Capan, A.; Oncul, S.; Cikrikci, S.; Taskiran, S.; Tasan, B.; Kaynak, F. B.; Ozbey, S.; Demchenko, A. P. Tetrahedron 2007, 63, 10290-10299.
23. Wu, Y.; Peng, X.; Fan, J.; Gao, S.; Tian, M.; Zhao, J.; Sun, S. J. Org. Chem. 2007, 72, 62-70.
24. Sinha, H. K.; Dogra, S. K. Chem. Phys. 1986, 102, 337-347.
25. Waluk, J. In Conformational Analysis of Molecules in Excited States; Waluk, J., Ed.; Wiley-VCH: New York, 2000; Chapter 2.
26. Douhal, A.; Amat-Guerrib, F.; Lillo, M. P.; Acuña, A. W. J. Photochem. Photobiol. A 1994, 78, 127-138.
27. Itoh, M.; Fujiwara, Y. J. Am. Chem. Soc. 1985, 107, 1561-1565.
28. Dupradeau, F. Y.; Case, D. A.; Yu, C. Z.; Jimenez, R.; Romesberg, F. E. J. Am. Chem. Soc. 2005, 127, 15612-15617.
29. Rini, M.; Kummrov, A.; Dreyer, J.; Nibbering, E. T. J.; Elsaesser, T. Faraday Discuss. 2003, 122, 27-40.
30. Krishnamoorthy, G.; Dogra, S. K. J. Lumin. 2001, 92, 91-102.
31. Balamurali, M. M.; Dogra, S. K. J. Photochem. Photobiol. A 2002, 154, 81-92.
32. Das, K.; Sarkar, N.; Majumdar, D.; Bhattacharyya, K. Chem. Phys. Lett. 1992, 198, 443-448.
33. Forés, M.; Duran, M.; Adamowicz, L. J. Phys. Chem. A 1999,103, 4413-4420.
34. Ríos, M. A.; Ríos, M. C. J. Phys. Chem. A 1998, 102, 1560-1567.
35. de Vivie-Riedle, R.; De Waele, V.; Kurtz, L.; Riedle, E. J. Phys. Chem. A 1999, 103, 10591-10599.
36. Das, K.; Sakar, N.; Ghosh, A. K.; Majumdar, D.; Nath, D. N.; Bhattacharyya, K. J. Phys. Chem. 1994, 98, 9126-9132.
37. Purkayastha, P.; Chattopadhyay, N. Phys. Chem. Chem. Phys. 2000, 2, 203-210.
38. Purkayastha, P.; Chattopadhyay, N. Int. J. Mol. Sci. 2003, 4, 335-361.
39. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Jr., Vreven; T. Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.
40. Hohenberg, P.; Kohn, W. Phys. Rev. B 1964, 136, 864-871.
41. Kohn, W.; Sham, L. J. Phys. Rev. A 1965, 140, 1133-1138.
42. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
43. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
44. Casida, M. E. In Recent Advances in Density Functional Methods, Part I; Chong, D. P., Ed.; World Scientific: Singapore, 1995; p 155.
45. Gross, E.; Dobson, J.; Petersilka, M. Top. Curr. Chem. 1996, 181, 81-172.
46. Foresman, J. B.; Head-Gordon, M.; Pople, J. A.; Frisch, M. J. J. Phys. Chem. 1992, 96, 135-149.
47. Vendrell, O.; Moreno, M.; Lluch, J. M. J. Chem. Phys. 2002, 117, 7525-7533.
48. Casadesús, R.; Vendrell, O.; Moreno, M.; Lluch, J. M. Chem. Phys. Lett. 2005, 405, 187-192.
49. Vendrell, O.; Gelabert, R.; Moreno, M.; Lluch, J. M. Chem. Phys. Lett. 2004, 396, 202-207.
50. Casadesús, R.; Moreno, M.; Lluch, J. M. J. Photochem. Photobiol. A 2005, 173, 365-374.
51. LeGourriérec, D.; Kharlanov, V.; Brown, R. G.; Rettig, W. J. Photochem. Photobiol. A 2000, 130, 101-111.
52. Vázquez, S. R.; Rodríguez, C. R.; Mosquera, M.; Prieto, F. R. J. Phys. Chem. A 2007, 111, 1814-1826.
53. Kharlanov, V. A.; Rettig, W.; Knyazhansky, M. I.; Makaraova J. Photochem. Photobiol. A 1997, 103, 45-50.
54. Dreuw, A.; Weisman, J. L.; Head-Gordon, M. J. Chem. Phys. 2003, 119, 2943-2946.
55. Sobolewski, A. L.; Domcke, W. Chem. Phys. 2003, 294, 73-83.