Abstract
The dipole moments in the equilibrium ground (μ g) and excited Franck–Condon states (μ e FC) of the molecules of 4′-(methoxy)-3-hydroxyflavone (FOM), 4′-(dimethylamino)-3-hydroxyflavone (FME), and 4′-N-(15-azacrown-5(-3-hydroxyflavone (FCR) in 1,4-dioxane were measured. Characteristic of these probes is excited-state intramolecular proton transfer. For comparison, the dipole moments of the molecules of 4′-(dimethylamino)-3-methoxyflavone (FME3ME) were measured, for which the excited-state intramolecular proton transfer is lacking. It is established that in the case of FME, FCR, and FME3ME the dipole moments μ g and μ e FC are parallel to the absorption transition dipole moment m a responsible for absorption. Among the compounds studied, FOM has the least values of μ g and μ e FC, only 9.4·10−30 and 26.3·10−30 C·m, respectively. The dipole moments μ g, μ e FC and m a are not parallel to one another, and the angles between them lie in the range 4–55°. This effect is due to FOM not having a strong electron-donating group, such as an amino group.
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REFERENCES
J. R. Lakowicz, Principles of Fluorescent Spectroscopy, 2nd edn., Plenum Press, New York (1999).
N. A. Nemkovich, V. I. Tomin, and A. N. Rubinov, in: J. R. Lakowicz (ed.), Topics+ in Fluorescence Spectroscopy, Vol. 2: Principles, Plenum Press, New York (1991), pp. 367–428.
A. Sytnik, D. Gormin, and M. Kasha, Proc. Natl. Acad. Sci., USA, 91, 11968–11972 (1994).
S. M. Ormson, R. G. Brown, F. Vollmer, and W. Rettig, J. Photochem. Photobiol. A: Chemistry, 81, 65–72 (1995).
V. G. Pivovarenko, A. V. Tuganova, A. S. Klimchenko, and A. P. Demchenko, Cellular Molecular Biol. Lett., 2, 355–364 (1997).
A. D. Roshal, A. V. Grigorovich, A. O. Doroshenko, V. G. Pivovarenko, and A. P. Demchenko, J. Phys. Chem. A, 102, 5907–5914 (1998).
A. D. Roshal, A. V. Grigorovich, A. O. Doroshenko, V. G. Pivovarenko, and A. P. Demchenko, J. Photochem. Photobiol. A: Chemistry, 127, 89–100 (1999).
N. A. Nemkovich, J. V. Kruchenok, A. N. Rubinov, V. G. Pivovarenko, and W. Baumann, J. Photochem. Photobiol. A: Chemistry, 139, 53–62 (2001).
O. P. Bondar, V. G. Pivovarenko, and E. S. Rowe, Biochim. Biophys. Acta, 1369, 119–130 (1998).
A. S. Klymchenko, T. Ozturk, V. G. Pivovarenko, and A. P. Demchenko, Can. J. Chem., 79, 358–363 (2001).
A. S. Klymchenko, T. Ozturk, V. G. Pivovarenko, and A. P. Demchenko, Tetrahedron Lett., 42, 7967–7970 (2001).
G. Duportail, A. S. Klymchenko, Y. Mely, and A. P. Demchenko, FEBS Lett., 508, 196–200 (2001).
W. Baumann, in: B. W. Rossiter, and J. F. Hamilton (eds.), Physical Methods of Chemistry, Vol. 3B, John Wiley & Sons (1989), pp. 45–131.
W. Rettig and W. Baumann, in: J. F. Ralek (ed.), Progress in Photochemistry and Photophysics, Vol. VI, CRC Press, Boca Raton (1992), pp. 79–134.
L. Peteanu and S. Locknar, Chem. Phys. Lett., 274, 79–84 (1997).
L. V. Premvardhan and L. A. Peteanu, J. Phys. Chem. A, 103, 7506–7514 (1999).
M. A. Smith, R. M. Neumann, and R. A. Webb, J. Heterocyclic Chem., 5, 425–431 (1968).
J. A. Riddick, W. B. Bunger, and T. K. Sakano, Organic Solvents, John Wiley & Sons (1986).
N. A. Nemkovich, W. Baumann, H. Reis, and N. Detzer, J. Photochem. Photobiol. A: Chemistry, 89, 127–133 (1995).
N. A. Nemkovich, W. Baumann, A. S. Kozlovsky, and H. Reis, Proc. SPIE, 2388, 335–346 (1995).
N. A. Nemkovich, W. Baumann, H. Reis, and Yu. V. Zvinevich, J. Photochem. Photobiol. A: Chemistry, 109, 287–292 (1997).
N. A. Nemkovich, H. Reis, and W. Baumann, J. Luminesc., 71, 255–263 (1997).
N. A. Nemkovich, W. Baumann, H. Reis, Yu. V. Zvinevich, and A. N. Rubinov, Opt. Spectrosc., 87, 735–741 (1999).
N. G. Bakhshiev (ed.), in: Solvatochromism: Problems and Methods [in Russian], Leningrad (1989).
W. Liptay, in: E. C. Lim (ed.), Excited States, Vol. 1, Academic Press, New York (1974).
W. Baumann, Z. Nagy, H. Reis, and N. Detzer, Chem. Phys, Lett., 224, 517–524 (1994).
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Nemkovich, N.A., Baumann, W., Pivovarenko, V.G. et al. Determination of the Dipole Moments of the Molecules of 4′-Substituted 3-Hydroxyflavones Using the Electrooptic Absorption Method. Journal of Applied Spectroscopy 70, 230–237 (2003). https://doi.org/10.1023/A:1023865101529
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DOI: https://doi.org/10.1023/A:1023865101529