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Fluorescence Quenching of Carbonyl-Twisted 5-Acyl-1-dimethylaminonaphthalenes by Alcohols.

ABSTRACT: Derivatives of 1-dimethylamino-5-propionylnaphthalene that constrain the carbonyl group into a five-, six-, and seven-membered ring were prepared, and their fluorescence quenching in protic solvents was studied. Evidence for enhanced quenching due to carbonyl twisting out of the molecular plane is presented, but this effect is heavily masked by the strong quenching by all of the derivatives and by the ring size-dependent deactivation seen in polar, aprotic solvents. Calculations show strong, ring size-dependent vibrational coupling between the carbonyl group and the naphthalene ring in the first excited state.

SUBMITTER: Anderson RS

PROVIDER: S-EPMC6714939 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature

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Fluorescence Quenching of Carbonyl-Twisted 5<b>-</b>Acyl-1-dimethylaminonaphthalenes by Alcohols.

Anderson Rachel S RS Nagirimadugu Newton V NV Abelt Christopher J CJ

ACS omega 20190815 9

Derivatives of 1-dimethylamino-5-propionylnaphthalene that constrain the carbonyl group into a five-, six-, and seven-membered ring were prepared, and their fluorescence quenching in protic solvents was studied. Evidence for enhanced quenching due to carbonyl twisting out of the molecular plane is presented, but this effect is heavily masked by the strong quenching by all of the derivatives and by the ring size-dependent deactivation seen in polar, aprotic solvents. Calculations show strong, rin ...[more]

PMID: 31497725

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