TD-DFT investigation of the potential energy surface for Excited-State Intramolecular Proton Transfer (ESIPT) reaction of 10-hydroxybenzo[h]quinoline: Topological (AIM) and population (NBO) analysis of the intramolecular hydrogen bonding interaction

Journal of Luminescence

Volumn 131, Issue 9, 2011, Pages 1918-1926

  Paul, Bijan Kumar ^a   Guchhait, Nikhil ^a  

^a UNIVERSITY OF CALCUTTA   (India)

Author keywords

10 hydroxybenzo h quinoline; Atoms In Molecule; Density Functional Theory; Excited State Intramolecular Proton Transfer; Hydrogen bond; Natural Bond Orbital

Indexed keywords

10-HYDROXYBENZO[H]QUINOLINE; ATOMS-IN-MOLECULE; DENSITY FUNCTIONALS; EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER; NATURAL BOND ORBITAL;

ATOMS; DENSITY FUNCTIONAL THEORY; GROUND STATE; HYDROGEN; HYDROGEN BONDS; MOLECULAR ORBITALS; OPTIMIZATION; PHOTOEXCITATION; POPULATION STATISTICS; POTENTIAL ENERGY; POTENTIAL ENERGY SURFACES; PROTON TRANSFER; RAPID THERMAL ANNEALING;

EXCITED STATES;

EID: 79956213782     PISSN: 00222313     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jlumin.2011.04.046     Document Type: Article

References (80)

1. A.H. Weller Z Elektrochem 60 1956 1144
2. A.H. Weller Prog. React. Kinet. 1 1961 187
3. H. Beens, K.H. Grellmann, M. Gurr, and A.H. Weller Discuss Faraday Soc 39 1965 183
4. B.K. Paul, A. Samanta, and N. Guchhait Photochem. Photobiol. Sci. 9 2010 57
5. B.K. Paul, A. Samanta, S. Kar, and N. Guchhait J. Photochem. Photobiol. A 214 2010 203
6. B.K. Paul, A. Samanta, and N. Guchhait J. Mol. Struct. 977 2010 78
7. A. Douhal, F. Lahmani, and A. Zewail Chem. Phys. 207 1996 477
8. J. Catalan, and J.L.G. de Paz J. Phys. Chem. A 105 2001 7315
9. M.J. Paterson, M.A. Robb, L. Blancafort, and A.D. DeBellis J. Am. Chem. Soc. 126 2004 2912
10. H. Mishra, H.C. Joshi, H.B. Tripathi, S. Maheshwary, N. Sathyamurthy, M. Panda, and J. Chrasekhar J. Photochem. Photobiol. A: Chem. 139 2001 23
11. P.B. Bisht, M. Okamoto, and S. Hirayama J. Phys. Chem. B 101 1997 8850
12. K.-Y. Chen, C.-C. Hsieh, C.-H. Lai, and P.-T. Chou Chem. Commun. 4395 2006
13. J. Catalan, P. Perez, J.C. del Valle, J.L.G. de Paz, and M. Kasha Proc. Natl. Acad. Sci., USA 99 2002 5793
14. J. Catalan, P. Perez, J.C. del Valle, J.L.G. de Paz, and M. Kasha Proc. Natl. Acad. Sci., USA 99 2002 5799
15. J.L. Herek, S. Pedersen, L. Banares, and A.H. Zewail J. Chem. Phys. 97 1992 9046
16. A.L. Sobolewski, and W. Domcke Phys. Chem. Chem. Phys. 8 2006 3410
17. J. Catalan, and J.C. del Valle J. Am. Chem. Soc. 115 1993 4321
18. J. Catalan, J.C. del Valle, R.M. Claramunt, D. Sanz, and J. Doctor J. Lumin 68 1996 165
19. H.J. Heller, and H.R. Blattmann Pure Appl. Chem. 36 1974 141
20. P.-T. Chou, M.L. Martinez, and J.H. Clements Chem. Phys. Lett. 204 1993 395
21. P.-T. Chou, D. MxMorrow, T.J. Aartsna, and M. Kasha J. Phys. Chem. 88 1984 4596
22. M.E. Balmer, H.-R. Buser, M.D. Muller, and T. Poiger Environ. Sci. Technol. 39 2005 953
23. K. Brunner, A. v. Dijken, H. Borner, J.J.A.M. Bastiaansen, N.M.M. Kiggen, and B.M.W. Langeveld J. Am. Chem. Soc. 126 2004 6035
24. J.S. Lim, J. Seo, and S.Y. Park J. Am. Chem. Soc. 128 2006 14542
25. R.B. Singh, S. Mahanta, and N. Guchhait J. Photochem. Photobiol. B: Biol 91 2008 1
26. B.K. Paul, A. Samanta, and N. Guchhait Langmuir 26 2010 3214
27. B.K. Paul, and N. Guchhait J. Phys. Chem. B 114 2010 12528
28. B.K. Paul, and N. Guchhait J. Colloid Interface Sci. 353 2011 237
29. P. Chowdhury, and S. Chakravorti Chem. Phys. Lett. 395 2004 103
30. K. Sahu, D. Roy, S.K. Mondal, R. Karmakar, and K. Bhattacharyya Chem. Phys. Lett. 404 2005 341
31. S. Sutton, N.L. Campbell, A.I. Cooper, M. Kirkl, W.J. Frith, and D.J. Adams Langmuir 25 2009 10285
32. M.L. Martinez, W.C. Cooper, and P.-T. Chou Chem. Phys. Lett. 193 1992 151
33. C. Schriever, M. Barbatti, K. Stock, A.J.A. Aquino, D. Tunega, S. Lochbrunner, E. Riedle, R. de Vivie-Riedle, and H. Lischka Chem. Phys. 347 2008 446
34. E.L. Roberts, P.T. Chou, T.A. Alexander, R.A. Agbaria, and I.M. Warner J. Phys. Chem. 99 1995 5431
35. P.-T. Chou, G.-R. Wu, Y.-I. Liu, W.-S. Yu, and C.-S. Chiou J. Phys. Chem. A 106 2002 5967
36. J.C. del Valle, and J. Catalan Chem. Phys. 270 2001 1
37. M. Ghedini, M. LaDeda, I. Aiello, and A. Grisolia Synth. Met. 138 2003 189
38. V. Kumar Rai, R. Srivastava, and M.N. Kamalasanan Synth. Met. 159 2009 177
39. H.-p. Shi, L. Xu, X.-f. Zhang, L.-q. Jiao, Y. Cheng, J.-y. He, J.-x. Yao, L. Fang, and C. Dong J. Mol. Struct. (THEOCHEM) 950 2010 53
40. R.F.W. Bader Atoms in Molecules, A quantum Theory 2000 Clarendon Press Oxford, UK
41. A.E. Reed, L.A. Curtiss, and F.A. Weinhold Chem. Rev. 88 1988 899
42. E.D. Glendening, A.E. Reed, J.E. Carpenter, F.A. Weinhold, NBO, Version 3.1, 1995.
43. P. Hobza, and Z. Havlas Chem. Rev. 100 2000 4253
44. B.K. Paul, S. Mahanta, R.B. Singh, and N. Guchhait J. Phys. Chem. A 114 2010 2618
45. S. Mahanta, B.K. Paul, R.B. Singh, and N. Guchhait J. Comput. Chem. 32 2011 1
46. D.-L. Wu, L. Liu, G.-F. Liu, and D.-Z. Jia J. Phys. Chem. A 111 2007 5244
47. I. Sciriha, and P.W. Fowler J. Chem. Inf. Model. 47 2007 1763
48. J.B. Foresman, and Æ. Frisch Exploring Chemistry with Electronic Structure Methods 2nd ed. 1996 Gaussian, Inc. Pittsburgh, PA
49. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., 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, 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, and J.A. Pople 2003 Gaussian, Inc. Pittsburgh PA
50. W.J. Hehre, L. Radom, P.V. Schleyer, and J.A. Pople Ab Initio Molecular Orbital Theory 1986 Wiley New York
51. R.G. Parr, and W. Yang Density-functional theory of atoms and molecules 1994 Oxford University Press
52. T. Clark, J. Chandrasekhar, G.W. Spitznagel, and P. v.R. Schleyer J. Comput. Chem. 4 1983 294
53. A.E. Shchavlev, A.N. Pankratov, and A.V. Shalabay J. Phys. Chem. A 109 2005 4137
54. A.L. Sobolewski, and W. Domcke Chem. Phys. 232 1998 257
55. S. Mahanta, R.B. Singh, D. Nath, and N. Guchhait J. Photochem. Photobiol. A 197 2008 62
56. S. Maheshwary, A. Chowdhury, N. Sathyamurthy, H. Mishra, H.B. Tripathi, M. Panda, and J. Chandrasekhar J. Phys. Chem. A 103 1999 6257
57. R. de Vivie-Riedle, V.D. Waele, L. Kurtz, and R.E. Riedle J. Phys. Chem. A 107 2003 10591
58. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, 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, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox 2009 Gaussian, Inc. Wallingford CT
59. K.S. David, A. Hemeryck, N. Tancrez, L. Toupet, J.A.G. Williams, I. Ledoux, J. Zyss, A. Boucekkine, J.P. Guégan, H.L. Bozec, and O. Maury J. Am. Chem. Soc. 128 2006 12243
60. I. Ciofini, P.P. Lainé, F. Bedioui, and C. Adamo J. Am. Chem. Soc. 126 2004 10763
61. A.S. Tiwary, and A.K. Mukherjee J. Mol. Struct. (THEOCHEM) 859 2008 107
62. T.-F. Miao, S. Li, and J. Cai J. Mol. Struct. (THEOCHEM) 855 2008 45
63. L.-C. Xu, J. Li, S. Shi, K.-C. Zheng, and L.-N. Ji J. Mol. Struct.(THEOCHEM) 855 2008 77
64. L. Miao, Y. Yao, F. Yang, Z. Wang, W. Li, and J. Hu J. Mol. Struct. (THEOCHEM) 865 2008 79 and references therein
65. S. Hirata, and M. Head-Gordon Chem. Phys. Lett. 302 1999 375
66. D. Maurice, and M. Head-Gordon J. Phys. Chem. 100 1996 6131
67. S. Nagaoka, and U. Nagashima Chem. Phys. 206 1996 353
68. S. Nagaoka, J. Kusunoki, T. Fujibuchi, S. Hatakenaka, K. Mukai, and U. Nagashima J. Photochem. Photobiol. A: Chem. 122 1999 151
69. S. Nagaoka, A. Nakamura, and U. Nagashima J. Photochem. Photobiol. A: Chem. 154 2002 23
70. J.N. Woodford J. Phys. Chem. A. 111 2007 8519
71. M. Palusiak, S. Simon, and M. Sola J. Org. Chem. 71 2006 5241
72. U. Koch, and P.L.A. Popelier J. Phys. Chem. 99 1995 9747
73. P.L.A. Popelier J. Phys. Chem. A 102 1998 1873
74. O. Galvez, P.C. Gomez, and L.F. Pacios J. Chem. Phys. 115 2001 11166
75. O. Galvez, P.C. Gomez, and L.F. Pacios J. Chem. Phys. 118 2003 4878
76. L. Senthilkumar, T.K. Ghanty, S.K. Ghosh, and P. Kolandaivel J. Phys. Chem. A 110 2006 12623
77. I. Alkorta, and J. Eguero J. Am. Chem. Soc. 124 2002 1488
78. M.F. Lucas, M.C. Michelini, N. Russo, and E. Sicilia J. Chem. Theory Comput. 4 2008 397
79. I. Alkorta, F. Blanco, and J. Elguero J. Chem. Theory Comput. 5 2009 1186
80. M. Montejo, A. Navarro, G.J. Kearley, and J.J. Lopez-Gonza lez J. Am. Chem. Soc. 126 2004 15087