Document Type

Article

Department/Program

Chemistry

Journal Title

Journal of Photochemistry and Photobiology A - Chemistry

Pub Date

6-15-2012

Volume

238

First Page

35

Abstract

The syntheses and photophysical properties of 1-(5-methylhexyl)-2,3,7,8-tetrahydro-1H-naphtho[2,1-e]indo1-9(6H)-one (7a) and 1-(5-methylhexyl)-23,8,9-terrahydro-1H-naphrho[2,1-e]indol-6(7H)-one (7b) are reported. They are prepared in eight steps from the corresponding bromonaphthylamines. These fluorescent compounds have PRODAN-like cores, and they are structurally similar to cholesterol. Compound 7a is the first reported PRODAN derivative where both the amino and carbonyl groups are constrained to be coplanar with the naphthalene core. Comparing the photophysical behavior of these compounds with related compounds indicates that locking the amino group in a five-membered ring enhances their desirable properties as solvent polarity sensors. (C) 2012 Elsevier B.V. All rights reserved.

DOI

10.1016/j.jphotochem.2012.04.011

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