Excited state intramolecular proton transfer of 2-hydroxy-1-naphthaldehyde semicarbazone: A combined fluorometric and quantum chemical study

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 222, Issue 1, 2011, Pages 220-227

  Bose, Debosreeta ^a   Jana, Barnali ^a   Datta, Sayanti ^a   Chattopadhyay, Nitin ^a  

^a JADAVPUR UNIVERSITY   (India)

Author keywords

DFT calculation; Excited state intramolecular proton transfer (ESIPT); Fluorescence; Potential energy curve

Indexed keywords

EID: 80051796196     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2011.06.001     Document Type: Article

References (50)

1. M. Kasha Proton-transfer spectroscopy. Perturbation of the tautomerization potential J. Chem. Soc. Faraday Trans. 2 82 1986 2379 2392
2. A. Douhal, S.K. Kim, and A.H. Zewail Femtosecond molecular dynamics of tautomerization in model base pairs Nature 378 1995 260 263
3. C.-L. Chen, C.-W. Lin, C.-C. Hsieh, C.-H. Lai, G.-H. Lee, C.-C. Wang, and P.-T. Chou Dual excited-state intramolecular proton transfer reaction in 3-hydroxy-2-(pyridin-2-yl)-4H-chromen-4-one J. Phys. Chem. A 113 2009 205 214
4. M.P. Lukeman, and P. Wan A new type of excited-state intramolecular proton transfer: proton transfer from phenol OH to a carbon atom of an aromatic ring observed for 2-phenylphenol J. Am. Chem. Soc. 124 2002 9458 9464 (Pubitemid 34856232)
5. K. Weber ber die enge beslehung der fluorescenzausloschung zur hemmungphotochemischer reaktionen Z. Phys. Chem. B 15 1931 18 44
6. T. Förster Fluoreszenzspektrum und wasserstoffionenkonzentration Naturwissenschaften 36 1949 186 187
7. A. Weller Fluorescence shifts of naphthols Z. Elektrochem. 56 1952 662 668
8. S.J. Formosinho, and L.G. Arnaut Excited-state proton transfer reactions. II. Intramolecular reactions J. Photochem. Photobiol. A: Chem. 75 1993 21 48
9. W. Frey, and T. Elsaesser Femtosecond intramolecular proton transfer of vibrationally hot molecules in the electronic ground state Chem. Phys. Lett. 189 1992 565 570
10. J. Seo, S. Kim, and S.Y. Park Strong solvatochromic fluorescence from the intramolecular charge-transfer state created by excited-state intramolecular proton transfer J. Am. Chem. Soc. 126 2004 11154 11155 (Pubitemid 39223180)
11. F.A.S. Chipem, and G. Krishnamoorthy Comparative theoretical study of rotamerism and excited state intramolecular proton transfer of 2-(2′-hydroxyphenyl)benzimidazole, 2-(2′-hydroxyphenyl)imidazo[4,5- b]pyridine, 2-(2′-hydroxyphenyl)imidazo[4,5-c] pyridine and 8-(2′-hydroxyphenyl)purine J. Phys. Chem. A 113 2009 12063 12070
12. S. Santra, G. Krishnamoorthy, and S.K. Dogra Excited-state intramolecular proton transfer in the anionic species of 2-(2′-acetamidophenyl) benzimidazole in aqueous medium Chem. Phys. Lett. 327 2000 230 237
13. N. Sarkar, K. Das, S. Das, A. Datta, D. Nath, and K. Bhattacharya Excited-state intramolecular proton transfer of 2-(2′-hydroxyphenyl) benzimidazole in micelles J. Phys. Chem. 99 1995 17711 17714
14. J. Catalan, F. Fabero, M.S. Guijarro, R.M. Claramunt, M.D.S. Maria, M.C. Foces-Foces, F.H. Cano, J. Elguero, and R. Sastre Photoinduced intramolecular proton transfer as the mechanism of ultraviolet stabilizers: a reappraisal J. Am. Chem. Soc. 112 1990 747 759 (Pubitemid 20093816)
15. P. Chou, D. McMorrow, T.J. Aartsma, and M. Kasha The proton-transfer laser. Gain spectrum and amplification of spontaneous emission of 3-hydroxyflavone J. Phys. Chem. 88 1984 4596 4599
16. A.U. Acuna, A. Costela, and J.M. Munoz A proton-transfer laser J. Phys. Chem. 90 1986 2807 2808
17. R.M. Tarkka, X. Zhang, and S.A. Jenekhe Electrically generated intramolecular proton transfer: electroluminescence and stimulated emission from polymers J. Am. Chem. Soc. 118 1996 9438 9439 (Pubitemid 26355147)
18. T. Nishiya, S. Yamauchi, N. Hirota, M. Baba, and I. Hanazaki Fluorescence studies of intramolecularly hydrogen-bonded o-hydroxyacetophenone, salicylamide, and related molecules J. Phys. Chem. 90 1980 5730 5735
19. G. Zhang, H. Wang, Y. Yu, F. Xiong, G. Tang, and W. Chen Diamond photodetector response to deep UV excimer laser excitation Appl. Phys. B: Lasers Opt. 76 2003 677 681
20. Y. Wu, X. Peng, J. Fan, S. Gao, M. Tian, J. Zhao, and S. Sun Fluorescence sensing of anions based on inhibition of excited-state intramolecular proton transfer J. Org. Chem. 72 2007 62 70 (Pubitemid 46068204)
21. A. Stynik, and M. Kasha Excited-state intramolecular proton transfer as a fluorescence probe for protein binding-site static polarity Proc. Natl. Acad. Sci. U.S.A. 91 1994 8627 8630 (Pubitemid 24273717)
22. T. Ozturk, A.S. Klymchenko, A. Capan, S. Oncul, S. Cikrikci, S. Taskiran, B. Tasan, F.B. Kaynak, S. Ozbey, and A.P. Demchenko New 3-hydroxyflavone derivatives for probing hydrophobic sites in microheterogeneous systems Tetrahedron 63 2007 10290 10299 (Pubitemid 47334830)
23. P. Purkayastha, and N. Chattopadhyay Role of rotamerisation and excited state intramolecular proton transfer in the photophysics of 2-(2′- hydroxyphenyl)benzoxazole, 2-(2′-hydroxyphenyl)benzimidazole and 2-(2′-hydroxyphenyl)benzothiazole: A theoretical study Phys. Chem. Chem. Phys. 2 2000 203 210
24. D.S. English, K. Das, K.D. Ashby, J. Park, J.W. Petrich, and E.W. Castner Jr. Confirmation of excited-state proton transfer and ground-state heterogeneity in hypericin by fluorescence upconversion J. Am. Chem. Soc. 119 1997 11585 11590 (Pubitemid 28006118)
25. G. Krishnamoorthy, and S.K. Dogra Excited state intramolecular proton transfer in 2-(2′-hydroxyphenyl)-3H-imidazo[4,5-b]pyridine: effect of solvents J. Lumin. 92 2001 91 102
26. R.B. Singh, S. Mahanta, S. Kar, and N. Guchhait Photo-physical properties of 1-hydroxy-2-naphthaldehyde: a combined fluorescence spectroscopy and quantum chemical calculations Chem. Phys. 331 2007 373 384
27. H. Mishra, S. Maheshwary, H.B. Tripathi, and N. Satyamurthy An experimental and theoretical investigation of the photophysics of 1-hydroxy-2-naphthoic acid J. Phys. Chem. A 109 2005 2746 2754 (Pubitemid 40519519)
28. J. Catalan, J.C. del Valle, J. Palomar, C. Diaz, and J.L.G. Paz The six-membered intramolecular hydrogen bond position as a switch for inducing an excited state intramolecular proton transfer (ESIPT) in esters of o-hydroxynaphthoic acids J. Phys. Chem. A 103 1999 10921 10934
29. W. Frey, F. Laermer, and T. Elsaesser Femtosecond studies of excited-state proton and deuterium transfer in benzothiazole compounds J. Phys. Chem. 95 1991 10391 10395
30. P. Chowdhury, S. Panja, and S. Chakravorti Excited state prototropic activities in 2-hydroxy 1-naphthaldehyde J. Phys. Chem. A 107 2003 83 90
31. M. Moriyama, M. Kosuge, S. Tobita, and H. Shizuka Excited-state intramolecular proton transfer followed by cis-trans isomerization of (1-hydroxy-2-naphthyl)-s-triazine derivatives Chem. Phys. 253 2000 91 103
32. Sahadev, R.K. Sharma, and S.K. Sindhwani Stabilities of some bivalent transition-metal ions with 2-hydroxy naphthaldehyde semicarbazones and thiosemicarbazones in dioxane-water mixtures - a potentiometric study Monatsh. Chem. 123 1992 1099 1105
33. Sahadev, R.K. Sharma, and S.K. Sindhwani Chelation behaviour of biologically activeo-hydroxy naphthaldehyde derivatives with bivalent metal ions in different solvents: a potentiometric study Proc. Indian Acad. Sci. (Chem. Sci.) 105 1993 103 110
34. D.D. Perrin, W.L.F. Armarego, and D.R. Perrin Purification of Laboratory Chemicals 1980 Pergamon Press New York
35. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman Jr., 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, 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 Gaussian 03, Revision C.01 2004 Gaussian, Inc. Wallingford, CT
36. S.P. De, S. Ash, S. Dalai, and A. Misra A DFT-based comparative study on the excited states intramolecular proton transfer in 1-hydroxy-2-naphthaldehyde and 2-hydroxy-3-naphthaldehyde J. Mol. Str.: Theochem. 807 2007 33 41
37. S. Mahanta, R.B. Singh, D. Nath, and N. Guchhait Photophysical properties of 2,3,6,7-tetrahydro-8-hydroxy-1H, 5H-benz[i,j] quinolizine-9-carboxaldehyde: Evidence of excited state intramolecular proton transfer but not of intramolecular charge transfer process J. Photochem. Photobiol. A: Chem. 197 2008 62 73
38. S. Mahanta, R.B. Singh, S. Kar, and N. Guchhait Evidence of coupled photoinduced proton transfer and intramolecular charge transfer reaction in para-N,N-dimethylamino orthohydroxy benzaldehyde: spectroscopic and theoretical studies Chem. Phys. 354 2008 118 129
39. B.K. Paul, S. Mahanta, R.B. Singh, and N. Guchhait A DFT-based theoretical study on the photophysics of 4-hydroxyacridine: single-water- mediated excited state proton transfer J. Phys. Chem. A 114 2010 2618 2627
40. A.D. Becke Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 98 1993 5648 5652
41. C. Lee, W. Yang, and R.G. Parr Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B 37 1988 785 789
42. J. Catalan, J. Palomar, and J.L.G. de Paz Intramolecular proton or hydrogen-atom transfer in the ground and excited states of 2-hydroxybenzoyl compounds J. Phys. Chem. A 101 1997 7914 7921 (Pubitemid 127591256)
43. M.J. Paterson, M.A. Robb, L. Blancafort, and A.D. DeBellis Theoretical study of benzotriazole UV photostability: ultrafast deactivation through coupled proton and electron transfer triggered by a charge-transfer state J. Am. Chem. Soc. 126 2004 2912 2922 (Pubitemid 38314297)
44. L. Onsager Electric moments of molecules in liquids J. Am. Chem. Soc. 58 1936 1486 1493
45. C.J.F. Bottcher Theory of electronic polarization vol. 1 1983 Elsevier Amsterdam
46. D.D. Perrin Dissociation Constants of Organic Bases in Aqueous Solution 1965 Butterworths London Supplement, 1972
47. K.-C. Wu, Y.-M. Cheng, Y.-S. Lin, Y.-S. Yeh, S.-C. Pu, Y.-H. Hu, J.-K. Yu, and P.-T. Che Competitive intramolecular hydrogen bonding formation and excited-state proton transfer reaction in 1-[(diethylamino)-methyl]-2-hydroxy-3- naphthaldehyde Chem. Phys. Lett. 384 2004 203 209
48. S. Tobita, M. Yamamoto, N. Kurahayashi, R. Tsukagoshi, Y. Nakamura, and H. Shizuka Effects of electronic structures on the excited-state intramolecular proton transfer of 1-hydroxy-2-acetonaphthone and related compounds J. Phys. Chem. A 102 1998 5206 5214 (Pubitemid 128588986)
49. D.R. Richardson, and P.V. Bernhardt Crystal and molecular structure of 2-hydroxy-1-naphthaldehyde isonicotinoyl hydrazone (NIH) and its iron(III) complex: an iron chelator with anti-tumour activity J. Biol. Inorg. Chem. 4 1999 266 273 (Pubitemid 29331015)
50. A.L. Sobolewski, and W. Domcke Ab initio study of excited-state intramolecular proton dislocation in salicylic acid Chem. Phys. 232 1998 257 265