Dual emission of temperature-induced betacarboline self-associated hydrogen bond aggregates

Photochemical and Photobiological Sciences

Volumn 8, Issue 3, 2009, Pages 414-420

  Hidalgo, José ^a   Sánchez Coronilla, Antonio ^a   Balón, Manuel ^a   Asunción Muñoz, María ^a   Carmona, Carmen ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BETA CARBOLINE; NITROGEN;

ARTICLE; CHEMICAL STRUCTURE; FLUORESCENCE; HYDROGEN BOND; LIGHT ABSORPTION; PRIORITY JOURNAL; PROTON TRANSPORT; TEMPERATURE;

EID: 61649122171     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b816776a     Document Type: Article

References (25)

1. A. Olba F. Tomas I. Zabala Photophysical behavior of norharmane related to proximity effect J. Luminescence 1990 47 27 34
2. A. Sánchez-Coronilla M. Balón M. A. Muñoz J. Hidalgo C. Carmona Ground state isomerism in betacarboline hydrogen bond complexes: The charge transfer nature of its large Stokes shifted emission Chem. Phys. 2008 351 27 32
3. M. Balón C. Carmona P. Guardado M. A. Muñoz Hydrogen-bonding and proton transfer interactions between harmane and trifluoroethanol in the ground and excited singlet states Photochem. Photobiol. 1998 67 414 419
4. C. Carmona M. Galán G. Angulo M. A. Muñoz P. Guardado M. Balón Ground and singlet excited state hydrogen bonding interactions of betacarbolines Phys. Chem. Chem. Phys. 2000 2 5076 5083
5. C. Carmona M. Balón M. Galán P. Guardado M. A. Muñoz Dynamic study of excited state hydrogen-bonded complexes of harmane in cyclohexane-toluene mixtures Photochem. Photobiol. 2002 76 239 246
6. 9-methyl harmane J. Phys. Chem. A 2001 105 10334 10338
7. C. Carmona M. Balón A. Sánchez-Coronilla M. A. Muñoz New insights on the excited-state proton-transfer reactions of betacarbolines: Cationic exciplex formation J. Phys. Chem. A 2004 108 1910 1918
8. M. Balón M. A. Muñoz P. Guardado C. Carmona Hydrogen-bonding interactions between harmane and pyridine in the ground and lowest excited singlet states Photochem. Photobiol. 1996 64 531 536
9. J. Hidalgo A. Sánchez-Coronilla M. A. Muñoz C. Carmona M. Balón Fluorescence quenching of betacarboline (9H-pyrido[3,4-b]indole) induced by intermolecular hydrogen bonding with pyridines J. Luminescence 2007 127 671 677
10. M. Miura J. Harada K. Ogawa Temperature-induced reversal of proton tautomerism: Role of hydrogen bonding and aggregation in 7-hydroxyquinolines J. Phys. Chem. A 2007 111 9854 9858
11. J. Catalán Photophysics of 1-azacarbazole dimers: A reappraisal J. Phys. Chem. A 2007 111 8774 8779
12. G. G. Doig J.D. Loudon P. McCloskey The chemistry of the mitragyna genus. Part IV. Derivatives, of harman J. Chem,. Soc. 1952 3912 3916
13. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A., Jr. 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. Sakrzewski, 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 D.0; Gaussian Inc., Pittsburgh, PA, 2003
14. A. D. Becke Density-functional thermochemistry. III. The, role of exact exchange J. Chem. Phys. 1993 98 5648 5652
15. C. Lee W. Yang R. G. Parr Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B 1988 37 785 789
16. M. A. Muñoz O. Sama M. Galán P. Guardado C. Carmona M. Balón Interactions between betacarboline and benzenoid π bases: FTIR evidence for the formation of NH-π hydrogen bonds J. Phys. Chem. B 1999 103 8794 8798
17. M. A. Muñoz P. Guardado M. Galán C. Carmona M. Balón A spectroscopy study of the molecular interactions of harmane with pyrimidine and other diazines Biophys. Chem. 2000 83 101 109
18. M. A. Muñoz O. Sama M. Galán P. Guardado C. Carmona M. Balón Hydrogen bonding NH/π interactions between betacarboline and methyl benzene derivatives Spectrochim. Acta Part A 2001 57 1049 1056
19. M. M. Martín N. Ikeda T. Okada N. Mataga Picosecond laser photolysis studies of deactivation processes of excited hydrogen-bonding complexes. 2. Dibenzocarbazole-pyridine systems J. Phys. Chem. 1982 86 4148 4156
20. H. Miyasaka A. Tabata S. Ojima N. Ikeda N. Mataga Femtosecond-picosecond laser photolysis studies on the mechanism of fluorescence quenching induced by hydrogen-bonding interactions-1.Pyrenol-pyridine systems J. Phys. Chem. 1993 97 8222 8228
21. S.G. Bertolotti C. M. Previtali The excited states quenching of safranine T by p-benzoquinones in polar solvents J. Photochem. Photobiol. A: Chem. 1997 103 115 119
22. J. Herbich M. Kijak A. Zielinska R.P. Thummel J. Waluk Fluorescence quenching by pyridine and derivatives induced by intermolecular hydrogen bonding to pyrrole-containing heteroaromatics J. Phys. Chem. A 2002 106 2158 2163
23. N. Mataga H. Chosrowjan S. Taniguchi Ultrafast charge transfer in excited electronic states and investigations into fundamental problems of exciplex chemistry: Our early studies and recent developments J. Photochem. Photobiol. C: Photochem. Rev. 2005 6 37 79
24. A.L. Sobolewski W. Domcke Computational studies of the photophysics of hydrogen-bonded molecular systems J. Phys. Chem. A 2007 111 11725 11735
25. M. F. Rode A. L. Sobolewski Photophysics of inter- and intra-molecularly hydrogen bonded systems: Computational studies on the pyrrole-pyridine complex and 2(2′-pyridyl)pyrrole Chem Phys. 2008 347 413 421