Abstract
Psoralens (furocoumarines) are photosensitizers of vegetative origin increasing the sensitivity of biological objects to near-ultraviolet radiation (UV-A, 320–400 nm). In the present work, the influence of substitution on the energy level diagram is considered for the first element of the series-psoralen. The absorption and fluorescence spectra are investigated with the use of an SM-2203 spectrofluorimeter, and theoretical calculations are carried out. In addition, the results obtained are compared with the calculated and experimental results of other authors. The employed method of intermediate neglect of differential overlap (INDO) yields such parameters as an oscillator force, nature and energy of the transition, positions of triplets and singlets, etc. The geometry is optimized by the semi-empirical PM3 method of the program Hyperchem 6.03. A comparison of the calculated results for the examined compounds demonstrates that after the substitution, the absorption spectra are shifted toward the red range. The lower excited singlet of the 21,22-dimethyl-10,11-cyclohexylpsoralen compound lies higher than that of psoralen and 10,11-phenyl-21,22-cyclohexylpsoralen; it is located at 332 nm. The absorption spectra from the excited states undergo a bathochromic shift after the substitution. The most intensive T-T absorption bands are also indicated in this work.
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References
A. Ya. Potapenko, V. A. Sukhorukov, and L. N. Bezdetnaya, Molecular Mechanisms of Biological Action of Optical Radiation, A. B. Rubin, ed. [in Russian], Nauka, Moscow (1988).
A. Ya. Potapenko, M. V. Malakhov, and A. A. Kyagova, Biofizika, 49, No. 2, 322–338 (2004).
E. Kleshchenko, Khim. Zhizn', No. 1, 50–57 (1996).
A. A. Krasnovskii, Jr., Biofizika, 49, No. 2, 305–321 (2004).
Q. A. Blan and L. I. Jrossweiner, Photochem. Photobiol., 45, No. 2, 177–183 (1987).
S. Caffieri, Photochem. Photobiol. Sci., 1, 149–157 (2002).
M. I. Dobrikov, Usp. Khim., 68, 1062–1079 (1999).
S. I. Antsipovich and T. S. Oretskaya, Usp. Khim., 67, 274–293 (1998).
G. V. Mayer, V. Ya. Artyukhov, O. K. Bazyl', et al., Electronically Excited States and Photochemistry of Organic Compounds [in Russian], Nauka, Novosibirsk (1997).
V. A. Svetlichnyi, T. N. Kopylova, G. V. Mayer, and I. N. Lapin, Russ. Phys. J., No. 9, 12–16 (2005).
J. Liano, J. Raber, and L. A. Eriksson, J. Photochem. Photobiol., A154, 235–243 (2003).
W. Mantulin and P. Song, J. Am. Chem. Soc., 95, No. 16, 5122–5129 (1973).
R. S. Becker, S. Chakravorti, and C. A. Gartner, J. Chem. Soc. Faraday Trans., 89, No. 1, 1007–1019 (1993).
V. G. Plotnikov, Nature of the Electronically Excited States and Spectral and Luminescent Properties of Polyatomic Molecules, Doctoral Thesis in Physical-Mathematical Sciences, Obninsk (1980).
V. G. Plotnikov and B. A. Dolgikh, Opt. Spektrosk., 43, No. 5, 882–890 (1977).
G. V. Mayer and V. I. Danilova, Quantum Chemistry: Structure, and Photonics of Molecules [in Russian], Publishing House of Tomsk State University, Tomsk (1992).
D. Bethea, B. Fullmer, S. Syed, et al., J. Dermatol. Sci., 19, 78–88 (1999).
Y. A. Parrish, T. B. Fitzpatric, L. Tanenbaum, and M. A. Pathak, J. Medicine. New England, 291, 1207–1211 (1974).
G. E. Dobretsov, Fluorescent Probes in a Study of Membrane Cells and Lipoproteins [in Russian], Nauka, Moscow (1989).
F. E. O. Suliman, S. S. Al-Kindi, S. M. Z. Al-Kindy, and H. A. J. Al-Lawati, J. Chromatogr., A101, 179–184 (2006).
L. G. Samsonova, R. M. Gadirov, V. V. Ishchenko, and O. Khilya, Opt. Spektrosk., 102, No. 6, 968–974 (2007).
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Translated from Izvestiya Vysshikh Uchebnykh Zavedenii, Fizika, No. 7, pp. 43–49, July, 2008.
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Bryantseva, N.G., Sokolova, I.V., Svetlichnyi, V.A. et al. Spectral and luminescent properties of sensitizers based on psoralen substitutes. Russ Phys J 51, 706–713 (2008). https://doi.org/10.1007/s11182-008-9099-x
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DOI: https://doi.org/10.1007/s11182-008-9099-x