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Fluorescence and photocycl1zation of N-naphthyl-substituted pyridinium cations

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The spectral-fluorescent and photochemical properties of 1-naphthyl-2,4-di- and 2,4,6-triphenylpyridinium perchlorates were investigated in solutions at 293 and 77 °K. The anomalously large Stokes shift of the fluorescence was due to the adiabatic change in the structure of the molecules as a result of rotations of the C- or N-aryl substituents. The observed phosphorescence arises as a result of intramolecular T-T transfer of energy to the N-naphthyl radical. 1-Naphthyl-2,4-diphenylpyridinium cations are capable of photocyclization with the formation of intensely fluorescent derivatives of benzo[b or c]pyrldo[1,2-f]phenanthridinium, isolated with high yields in preparative photolysis.

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Authors and Affiliations

  1. Scientific Research Institute of Physical and Organic Chemistry at M. A. Suslov Rostov State University, 344090, Rostov-on-Don

    Ya. R. Tymyanskii, V. M. Feingel'man, M. I. Knyazhanskii & N. V. Kholodova

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  1. Ya. R. Tymyanskii
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  2. V. M. Feingel'man
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  3. M. I. Knyazhanskii
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  4. N. V. Kholodova
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1528–1532, November, 1984.

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Tymyanskii, Y.R., Feingel'man, V.M., Knyazhanskii, M.I. et al. Fluorescence and photocycl1zation of N-naphthyl-substituted pyridinium cations. Chem Heterocycl Compd 20, 1262–1266 (1984). https://doi.org/10.1007/BF00505719

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  • DOI: https://doi.org/10.1007/BF00505719

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