Abstract
Fluorescence spectra of N-substituted 2-(2-aminophenyl)-4H-3,1-benzoxazin-4-ones consist of two bands, the long-wavelength band with anomalous Stokes shift, which corresponds to the emission of the product of intramolecular photoinduced proton transfer, and the short-wavelength band belonging to the form in which proton transfer does not occur. It is assumed that there is equilibrium between two planar rotamers in the ground state: one with the N-H…N hydrogen bond in which the intramolecular photoinduced proton transfer occurs and the other with the N-H…O bond, which does not experience hydrogen transfer. According to ab initio quantum-chemical calculations, the potential energy of proton transfer in the first excited singlet state has a potential barrier of 2.1–26.8 kJ/mol depending on the electron-withdrawing ability of the substituent on the amino group.
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Original Russian Text © M.N. Khimich, E.A. Birgen, B.M. Bolotin, B.M. Uzhinov, 2009, published in Khimiya Vysokikh Energii, 2009, Vol. 43, No. 2, pp. 167–172.
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Khimich, M.N., Birgen, E.A., Bolotin, B.M. et al. Intramolecular photoinduced proton transfer in 2-(2-aminophenyl)-4H-3,1-benzoxazin-4-ones with different electron-withdrawing N-substituents. High Energy Chem 43, 123–128 (2009). https://doi.org/10.1134/S001814390902009X
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DOI: https://doi.org/10.1134/S001814390902009X