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1,5-Prodan Emits from a Planar Intramolecular Charge-Transfer Excited State

Chen, Tao
Lee, Samuel W.
Abelt, Christopher J.
Abstract
1-Propionyl-5-dimethylaminonaphthalene (8, 1,5-Prodan) and two derivatives where the amino group is constrained in a seven-membered (9) and five-membered (10) ring are prepared. All three exhibit strong fluorescence and similar degrees of solvatochromism. Their fluorescence is strongly quenched in alcohol solvents. Because the amino group in 9 and especially 10 is forced to be coplanar with the naphthalene ring, the similar photophysical behavior of all three suggests that emission arises from a planar excited state (planar intramolecular charge transfer).
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2018-05-02
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Chemistry
DOI
https://doi.org/10.1021/acsomega.8b00423
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