Solvent effects on the photophysics of 3-(Benzoxazol-2-yl)-7-(N, N-diethylamino)chromen-2-one

Photochemical and Photobiological Sciences

Volumn 3, Issue 1, 2004, Pages 79-84

  Machado, Antonio Eduardo Da Hora ^a   Severino, Divinomar ^a   Ribeiro, Juliana ^a   De Paula, Rodrigo ^a   Gehlen, Marcelo Henrique ^b   de Oliveira, Hueder Paulo Moisés ^b   Matos, Mauricio Dos Santos ^b   De Miranda, Jacques Antonio ^a  

^a FEDERAL UNIVERSITY OF UBERLÂNDIA   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

2 BUTANOL; 2 PROPANOL; 3 (BENZOXAZOL 2 YL) 7 (N,N DIETHYLAMINO)CHROMEN 2 ONE; ACETIC ACID ETHYL ESTER; ACETONE; ACETONITRILE; ALCOHOL; AMINE; CARBON TETRACHLORIDE; CHLOROFORM; CHROMENE DERIVATIVE; COUMARIN DERIVATIVE; CYCLOHEXANE; CYCLOHEXANE DERIVATIVE; DECANE; DICHLOROMETHANE; DIISOPROPYLAMINE; DIMETHYL SULFOXIDE; DIOXANE; ETHYLENE GLYCOL; HEXANE; HYDROGEN; LIQUID PARAFFIN; METHANOL; METHYLCYCLOHEXANE; N,N DIMETHYLFORMAMIDE; SOLVENT; TETRAHYDROFURAN; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; DATA ANALYSIS; FLUORESCENCE ANALYSIS; HYDROGEN BOND; MICELLE; PHYSICS; PRIORITY JOURNAL; QUANTUM MECHANICS; QUANTUM YIELD; SOLUTE; SOLVENT EFFECT;

EID: 3042602301     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b308121d     Document Type: Article

References (37)

1. J. K. Thomas Characterization of surfaces by excited states J. Phys. Chem. 1987 91 267-276.
2. G. A. Reynolds K. H. Drexhage New coumarin dyes with rigized structure for flashlamp-pumped dye lasers Opt. Commun. 1975 222-225.
3. U. Brackmann, Lambdachrome Laser Dyes, Lambda Physik, Gmbh, Göttingen, 1986.
4. B. M. Krasovitskii, in Organic Luminescent Materials, ed. B. M. Krasovitskii and B. M. Bolotin, VCH, Weinheim, 1988, ch. 7.
5. K. H. Drexhage, Topics in Applied Physics, Vol. 1, Dye Lasers, ed. F. P. Schäfer, Springer, Berlin, 1973.
6. F. Dall’Acqua, D. Vedaldi and S. Caffieri, in The Fundamental Bases of Phototherapy, ed. H. Hönigsmann, G. Jori and A. R. Young, OEMF, Milan, 1996, pp. 1–16.
7. M. Maeda, Laser Dyes, Academic Press, New York, 1984.
8. R. M. Christie Fluorescent dyes, a review Rev. Prog. Color. Relat. Top. 1993 23 1-18.
9. R. M. Christie H. Lui Studies of fluorescent dyes: part 1. An investigation of the electronic spectral properties of substituted coumarins Dyes Pigm. 1999 42 85-93.
10. N. Chandrasekharan L. Kelly Fluorescent molecular thermometers based on monomer/exciplex interconversion The Spectrum 2002 15 1-7.
11. J. Sokolowska W. Czajkowski R. aw Podsiadly The photostability of some fluorescent disperse dyes derivatives of coumarin Dyes Pigm. 2001 49 187-191.
12. C. E. Wheelock The fluorescence of some coumarins J. Am. Chem. Soc. 1959 81 1348-1352.
13. G. Jones II, in Dye Laser – Principles and Applications, ed. F. D. Duarte and L. W. Hillman, Academic Press, New York, 1990, pp. 287–345.
14. X. H. Luan N. M. F. S. A. Cerqueira A. M. A. G. Oliveira M. M. M. Raposo L. M. Rodrigues P. Coelho A. M. F. Oliveira-Campos Synthesis of fluorescent 3-benzoxazol-2-yl-coumarins Adv. Colour Sci. Technol. 2002 5 18-23.
15. D. F. Eaton Fluorescence materials for fluorescence measurement Pure Appl. Chem. 1988 60 1107-1114.
16. g) sensitization J. Photochem. Photobiol., A 1994 79 11-17.
17. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle and J. A. Pople, Gaussian 98W, Revision A11.4, Gaussian, Inc., Pittsburgh, PA, USA, 2002.
18. HyperChem 5.11, Computational Chemistry Program, Hypercube Inc., Gainesville, FL, USA, 1996.
19. A. E. H. Machado J. A. Miranda S. Guilardi D. E. Nicodem D. Severino Photophysics and spectroscopic properties of 3-benzoxazol-2-yl-chromen-2-one Spectrochim. Acta, Part A 2003 59 345-355.
20. A. E. H. Machado J. A. Miranda Photophysical/quantum mechanical characterization of the compound 3-benzoxazol-2-yl-7-hydroxy-chromen-2-one J. Photochem. Photobiol., A 2001 141 109-116.
21. J. R. Lakowicz, Principles of Fluorescence Spectroscopy, Kluwer Academic/Plenum Publishers, New York, 2nd edn., 1999.
22. N. J. Turro, Modern Molecular Photochemistry, University Science Books, New York, 1991.
23. A. Gilbert and J. Baggott, Essentials of Molecular Photochemistry, Blackwell, Oxford, 1991.
24. A. B. J. Parusel G. Kökler S. Grimme Density functional study of excited charge transfer state formation in 4-(N, N-dimethylamino)benzonitrile J. Phys. Chem. A 1998 102 6297-6306.
25. A. B. J. Parusel Excited state intramolecular charge transfer in N, N-heterocyclic-4-aminobenzonitriles: a DFT study Chem. Phys. Lett. 2001 340 531-537.
26. 2(TICT) a partir da excitação eletrônica do composto 3-benzoxazol-2-il-7-(N, N-dietilamino)-cromen-2-ona, Presentation to be given at XII Simpósio Brasileiro de Química Teórica, Caxambu, MG, Brazil, November, 2003.
27. 1(n,π*) state J. Phys. Chem. 1994 98 6054-6058.
28. C. Reichardt Solvatochromic dyes as solvent polarity indicators Chem. Rev. 1994 94 2319-2358.
29. P. Suppan Solvatochromic shifts: the influence of the medium on the energy of electronic states J. Photochem. Photobiol., A 1990 50 293-330.
30. Z. R. Grabowski K. Rotkiewcz A. Siemiarczuk D. J. Cowley W. Baumann Twisted intramolecular charge transfer state (TICT)– New class of excited states with a full charge separation Nouv. J. Chim. 1979 3 443-454.
31. K. Rotkiewcz K. H. Grellmann Z. R. Grabowski Reinterpretation of the anomalous fluorescence of p-N, N-dimethylamino-benzonitrile Chem. Phys. Lett. 1973 19 315-318.
32. K. A. Zachariasse M. Grobys Th. von der Haar A. Hebecker Yu.-V. Il’ichev O. Morawski I. Rückert W. Kühnle Photoinduced intramolecular charge transfer and internal conversion in molecules with a small energy gap between S-1 and S-2. Dynamics and structure J. Photochem. Photobiol., A 1997 105 373-383.
33. K. A. Zachariasse M. Grobys Th. von der Haar A. Hebecker Yu. V. Il’ichev Y.-B. Jiang O. Morawski W. Kuhnle Intramolecular charge transfer in the excited state. Kinetics and configurational changes J. Photochem. Photobiol., A 1996 102 59-70.
34. J. A. de Miranda, Caracterização Fotofísica de Cumarinas, MSc Dissertation, Universidade Federal de Uberlândia, MG, Brazil, 2001.
35. W.-M. Kwok M. W. George D. C. Grills C. Ma P. Matousek A. W. Parker D. Phillips W. T. Toner M. Towrie Direct observation of a hydrogen-bonded charge-transfer state of 4-dimethylamino-benzonitrile in methanol by time-resolved IR spectroscopy Angew. Chem., Int. Ed. 2003 42 1826-1830.
36. R. W. Redmond S. E. Braslavsky Time-resolved thermal lensing and phosphorescence studies on photosensitizer singlet molecular oxygen formation. Influence of the electronic configuration of the sensitizer on sensitisation efficiency Chem. Phys. Lett. 1988 148 523-529.
37. K. I. Priyadarshini B. Naik P. N. Murthy A study of the triplet state of 7-amino coumarin laser dye by the nanosecond pulse radiolysis technique J. Photochem. Photobiol., A 1990 54 251-261.