Photophysical Properties of Derivatives of 1H-Pyrazolo[3,4-b]quinoline and 1H-Pyrazolo[3,4-b]quinoxaline

• Autorzy: Mac M. , Uchacz T. , Andrzejak M. , Danel A. , Szlachcic P. , Nowak P.
• Języki publikacji: EN

Abstrakty

EN

The fluorescence behaviour of 1,3-diphenyl-1H-pyrazolo[3,4-b]quinoline (PQ1), 1,3- diphenyl-1H-pyrazolo[3,4-b]quinoxaline (PQX1) and 3-methyl-1-phenyl-1H-pyrazolo[ 3,4-b]quinoxaline (PQX2) has been compared. It has been established that these dyes form exciplexes with N,N-dimethylaniline (DMA) and p-cyano N,N -dimethylaniline (DMABN) in weakly polar dibutyl ether. The reduction potential of these compounds has been measured by cyclic voltammetry. The different behaviour with respect to intersystem crossing process in pyrazoloquinoline and pyrazoloquinoxalines has been explained in terms of larger energy gap between the first excited singlet state and the higher triplet state having a different symmetry in the former system. This is supported by quantum chemical calculations and it explains the lack of the triplet-triplet absorption bands in the flash photolysis experiments in pyrazoloquinoline system in any solvent.

Słowa kluczowe

EN

charge transfer fluorescence; intersystem crossing; reduction potential; exciplex fluorescence

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2007
• Tom: Vol. 81, nr 4
• Opis fizyczny: s. s. 557--572, Bibliogr. 17 poz., rys.

Twórcy

autor

Mac M.

autor

Uchacz T.

autor

Andrzejak M.

autor

Danel A.

autor

Szlachcic P.

autor

Nowak P.

• Faculty of Chemistry, Jagiellonian University, 30-060 Kraków, Ingardena St. 3, Poland,

Bibliografia

• 1. Mac M., Danel A., Wisla A., Karocki A. And Krolicki R., J. Photochem. Photobiol. A: Chem., 180, 88 (2006).
• 2. Mac M., Uchacz T., Andrzejak M., Danel A. and Szlachcic P., J. Photochem. Photobiol. A: Chem., (in press).
• 3. Sachs F. And Becherescu P., Ber., 36,1136 (1903).
• 4. Meech S.R. And Phillips D.,J. Photochem, 193 (1983).
• 5. Mac M., Kwiatkowski P. and Turek A.M., J. Lumin., 65, 341 (1996).
• 6. Andrzejak M., Mazur G. and Petelenz P., J. Mol. Struct. (Theochem), 527, 91 (2000).
• 7. Becke A.D., J. Chem. Phys., 98, 5648 (1993).
• 8. Lee C., Yang W. and Parr R.G., Phys. Rev. B, 37, 785 (1988).
• 9. Miehlich B., Savin A., Stoll H. and Preuss H., Chem. Phys. Lett., 157, 200 (1989).
• 1O. Gaussian 03, Revision C.02, Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery, Jr J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., lyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., RegaN., 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., 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 L, Martin R.L., Fox D.J., Keith T, Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gili P.M.W., Jahnson B., Chen W., Wong M.W., Gonzalez C. and Popie J.A., Gaussian, Inc., Wallingford CT, 2004.
• 11. Lippert E., Z. Naturforsch., l0a, 541 (1955), MatagaN., Kaifu Y. and Koizumi M., Bull. Chem. Soc. Jpn, 28,690(1955).
• 12. Beens H. and Weller A., Acta Phys. Polon., 34, 593 (1968).
• 13. Mac M., Danel K. and Andrzejak M., Polish J. Chem., 80, 1737 (2006).
• 14. Mac M., Kwiatkowski P. and Turek A.M., Chem. Phys. Lett., 250, 104 (1996).
• 15. Mac M., Polish J. Chem., 77, 427 (2003).
• 16. Kucybała Z., Kosobucka A. and Pączkowski J.,J. Photochem. Photobiol. A: Chem., 136,227 (2000).
• 17. El-Sayed M., J. Chem. Phys., 38, 2834 (1963); Becker R.S., 'Theory and interpretation of fluorescence and phosphorescence, Wiley Interscience, New York, 1969, pp. 155-189.