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Carbonyl-twisted 6-acyl-2-dialkylaminonaphthalenes as solvent acidity sensors.

ABSTRACT: Derivatives of 2-propionyl-6-dimethylaminonaphthalene (PRODAN) with twisted carbonyl groups were investigated as highly responsive sensors of H-bond donating ability. The PRODAN derivative bearing a pivaloyl group (4) was prepared. The torsion angle between the carbonyl and naphthalene is 26° in the crystal. It shows solvatochromism that is similar to five other PRODAN derivatives (1-3, 5, 6). Twisted-carbonyl derivatives 3, 4, and 6 show strong fluorescence quenching in protic solvents. The order of magnitude of the quenching is linearly related to the H-bond donating ability of the solvent (SA) but not to other solvent properties. Binary mixtures of protic solvents show specific interaction effects with respect to quenching and solvatochromism. Aggregation in water is an issue with the pivaloyl derivatives.

SUBMITTER: Green AM

PROVIDER: S-EPMC3511668 | biostudies-literature | 2013 Mar

REPOSITORIES: biostudies-literature

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Carbonyl-twisted 6-acyl-2-dialkylaminonaphthalenes as solvent acidity sensors.

Green Amy M AM Naughton Hannah R HR Nealy Zachariah B ZB Pike Robert D RD Abelt Christopher J CJ

The Journal of organic chemistry 20120821 5

Derivatives of 2-propionyl-6-dimethylaminonaphthalene (PRODAN) with twisted carbonyl groups were investigated as highly responsive sensors of H-bond donating ability. The PRODAN derivative bearing a pivaloyl group (4) was prepared. The torsion angle between the carbonyl and naphthalene is 26° in the crystal. It shows solvatochromism that is similar to five other PRODAN derivatives (1-3, 5, 6). Twisted-carbonyl derivatives 3, 4, and 6 show strong fluorescence quenching in protic solvents. The ord ...[more]

PMID: 22894649

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