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Fluoreszenzspektren, Photodissoziation und Phototautomerie einiger 4-Hydroxycumarine Lumineszierende Heterocyclen, 5. Mitt.

Fluorescence spectra, photodissociation, and phototautomerism of some 4-hydroxycoumarines

  • Organische Chemie und Biochemie
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Abstract

Absorption and emission spectra as well as pK a-values of the following compounds have been measured: 4-Hydroxycoumarin coumarin (pK a=4,14), 7-dimethylamino-4-hydroxycoumarin (6,5), 4,7-dihydroxycoumarin (4,74 and 9,46) and 1-methyl-4-hydroxycarbostyril (5,9). The most strongly fluorescent 4-hydroxycoumarines are those having electron donating substituents in position 7. 4-Hydroxycoumarin itself fluorescences in solutions of pH>5 as the anion, at pH<4 as the neutral molecule. Unlike its 7-hydroxy isomer it does not exhibit any phototautomerism, since pK a-values of ground and excited state are identical. A similar behaviour is found in the case of 7-dimethylamino-4-hydroxycoumarin, which in acidic solution forms a photokation, and of 1-methyl-4-hydroxycarbostyril. Contrarily 4,7-dihydroxycoumarin shows complex multiple fluorescences. Emission bands from 391 to 445 nm are assigned to di- and monoanionic, neutral and cationic forms and to phototautomers. A marked fluorescence solvatochromism of 7-dimethylamino-4-hydroxycoumarin and of 4,7-dihydroxycoumarin is indicating a highly polar excited state.

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  1. Institut für Organische Chemie, Universität Graz, Heinrichstraße 28, A-8010, Graz, Österreich

    Otto S. Wolfbeis & Georg Uray

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  1. Otto S. Wolfbeis
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  2. Georg Uray
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Wolfbeis, O.S., Uray, G. Fluoreszenzspektren, Photodissoziation und Phototautomerie einiger 4-Hydroxycumarine Lumineszierende Heterocyclen, 5. Mitt.. Monatshefte für Chemie 109, 123–136 (1978). https://doi.org/10.1007/BF00911952

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  • DOI: https://doi.org/10.1007/BF00911952

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