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. 2016 May 26;120(20):3518-23.
doi: 10.1021/acs.jpca.6b02398. Epub 2016 May 5.

Intramolecular Hydrogen-Bonding Effects on the Fluorescence of PRODAN Derivatives

Affiliations

Intramolecular Hydrogen-Bonding Effects on the Fluorescence of PRODAN Derivatives

Isaac G Alty et al. J Phys Chem A. .

Abstract

The effects of intramolecular hydrogen-bonding on the fluorescence behavior of three derivatives of 6-propionyl-2-dimethylaminonaphthalene are reported. The H-bonding effects are revealed through comparisons with corresponding reference compounds in which the H-bond-donating hydroxyl groups are replaced with methoxy groups. In toluene, intramolecular H bonding gives rise to a dramatic increase in the fluorescence intensity but only a slight red shift in the position. This behavior is attributed to decreased efficiency in intersystem crossing due to an increase in the energy of the n → π* triplet state. The intramolecular H bond does not induce quenching in acetonitrile; however, in the presence of a very small concentration of methanol, a dual intramolecular, intermolecular H-bonding arrangement does lead to partial quenching as revealed by preferential solvation studies.

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