Hydrogen Bonding Effect on the Fluorescence of π-Electron System. III. Fluorescence Quenching of Some Nitrogen Heterocycles Caused by Hydrogen Bond Formation

Bulletin of the Chemical Society of Japan - Tập 30 Số 7 - Trang 711-715 - 1957
Noboru Mataga1, Shizuyo Tsuno1
1Institute of Polytechnics, Osaka City University

Tóm tắt

Abstract 1. Hydrogen bonding effect on the fluorescence of acridine, 3,6-diaminoacridine and 3,6-bisdimethylaminoacridine was studied in non-polar solvent added with proton donors such as phenol, naphthols, aniline and pyrrole. 2. Their fluorescence yields are decreased when hydrogen bonded with these proton donors, in which the hydrogen bond is capable of conjugation with π-electron system, in contrast to the case of donors such as benzylalcohol and β-phenylethylalcohol in which the hydrogen bond is isolated by σ-bond from π-electron system, and hydrogen bonding with which leads to the enhancement of fluorescence yield. 3. No viscosity dependence of quenching has been observed. From this fact participation of diffussion controlled dynamical process in the non-radiative degradation of excited state is unlikely. 4. The cause of non-radiative degradation of excited state by hydrogen bonding was ascribed to the delocalization of π-electrons through the hydrogen bond, especially in the excited state.

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