Abstract
Adsorption interactions of trans-stilbene and its hydroxy and methoxy derivatives with the surface of nanodispersed SiO2 aerogel were studied by diffuse-reflection FTIR spectroscopy. Stilbenes were found to adsorb at the aerosil via hydrogen bonding to silanol OH groups. The deepest modification of these groups was produced by 3,5,4′-trihydroxystilbene (resveratrol). Although the stilbenes adsorbed reversibly, the absorption spectra of the starting and desorbed resveratrol proved to differ. UV irradiation (λ = 285–305 nm) of adsorbed hydroxystilbenes changed the composition and properties of adsorbed layers. The changes include breaking of the hydrogen bonds between the hydroxystilbene molecules and the surface, destruction of the stilbenes involving cleavage of the double bond of the ethene fragment, dimerization, oxidation, and transformation into other compounds. The intensity of heterogeneous photolysis depends on the number and composition of functional groups in trans-stilbenes.
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Golovkin, B.N., Rudenskaya, R.N., Trofimova, I.A., et al., Biologicheski aktivnye veshchestva rastitel’nogo proiskhozhdeniya (Biologically Active Compounds of Plant Origin), 3 vols., Moscow: Nauka, 2001.
Jang, M., Cai, L., Udeani, G.O., et al., Science, 1997, vol. 275, p. 218.
King, R., Bomser, J.A., and Min, D.B., Comp. Rev. Food Sci. Food Saf., 2006, vol. 5, no. 3, p. 65.
Waldeck, D.H., Chem. Rev., 1991, vol. 91, p. 415.
Papper, V. and Likhtenshtein, G.I., J. Photochem. Photobiol., A, 2001, vol. 140, p. 39.
Minkin, V.I., Ross. Khim. Zh. (Zh. Ross. Khim. O-va. im. D.I. Mendeleeva), 2000, vol. 45, no. 6, p. 3.
Mayer, T.S., Mallouk, T.E., and Natan, M.J., Adv. Mater., 1999, vol. 11, p. 1021.
Larin, A.V. and Polunin, K.E., Sorbts. Khromatogr. Protsessy, 2003, vol. 3,issue 3, p. 268.
Polunin, K.E., Polunina, I.A., and Roldugin, V.I., Sorbts. Khromatogr. Protsessy, 2003, vol. 3,issue 5, p. 567.
Polunin, K.E., Kolotilov, P.N., and Polunina, I.A., Sorbts. Khromatogr. Protsessy, 2007, vol. 7,issue 1, p. 28.
Kolotilov, P.N., Shepelev, B.N., Polunina, I.A., et al., Sorbts. Khromatogr. Protsessy, 2005, vol. 5,issue 1, p. 82.
Bellamy, L., Advances in Infrared Group Frequences, Bungay, 1968.
Kiselev, A.V. and Lygin, V.I., Infrakrasnye spektry poverkhnostnykh soedinenii (Infrared Spectra of Surface Compounds), Moscow: Nauka, 1972.
Vibrational Spectra and Structure, During, I.R., Ed., New York: Elsevier, 1986, vol. 16.
Smith, A., Applied Infrared Spectroscopy: Fundamentals, Techniques, and Analytical Problem-Solving, New York: Wiley, 1979.
Molina, V., Merchan, M., and Roos, B.O., Spectrochim. Acta, A, 1999, vol. 55, no. 3, p. 433.
Tyukavkina, N.A., Gromova, A.S., Lutskii, V.I., et al., Khim. Prir. Soedin., 1972, vol. 8, no. 5, p. 600.
Pere, E., Cardy, H., Cairon, O., et al., Vib. Spectrosc., 2001, vol. 25, no. 2, p. 163.
Iler, R.K., The Chemistry of Silica, New York: Wiley, 1979.
Sigman, M.E., Barbas, J.T., Corbett, S., et al., J. Photochem. Photobiol., A, 2001, vol. 138, p. 269.
Potapov, V.M., Stereokhimiya (Stereochemistry), Moscow: Khimiya, 1988, p. 116.
Tertykh, V.A. and Belyakova, L.A., Khimicheskie reaktsii s uchastiem poverkhnosti kremnezema (Chemical Reactions Involving the Silica Surface), Kiev: Naukova Dumka, 1991, p. 5.
Li, W., Li, B., and Chen, Y., Phytochemistry, 1998, vol. 49, no. 5, p. 1393.
Meier, H., Angew. Chem., Int. Ed., 1992, vol. 31, p. 1399.
Nurmukhametov, R.N., Pogloshchenie i lyuminestsentsiya aromaticheskikh soedinenii (Absorption and Luminescence of Arenes), Moscow: Khimiya, 1971, p. 57.
Kremnezemy v meditsine i biologii (Silicas in Medicine and Biology), Chuiko, A.A., Ed., Kiev: Stavropol’, 1993, p. 3.
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Original Russian Text © K.E. Polunin, N.P. Sokolova, A.M. Gorbunov, R.A. Bulgakova, I.A. Polunina, 2008, published in Fizikokhimiya Poverkhnosti i Zashchita Materialov, 2008, Vol. 44, No. 4, pp. 378–384.
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Polunin, K.E., Sokolova, N.P., Gorbunov, A.M. et al. FTIR spectroscopic studies of interactions of stilbenes with silicon dioxide. Prot Met 44, 352–357 (2008). https://doi.org/10.1134/S0033173208040061
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DOI: https://doi.org/10.1134/S0033173208040061