Does PRODAN Possess an O-TICT Excited State? Synthesis and Properties of Two Constrained Derivatives

Overview

Journal J Phys Chem A

Publisher American Chemical Society

Specialty Chemistry

Date 2010 Mar 25

PMID 20329761

Citations 11

Authors

Renata K Everett

H A Ashley Nguyen

Christopher J Abelt

Affiliations

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Abstract

The synthesis and photophysical properties of 7-(dimethylamino)-3,4-dihydrophenanthren-1(2H)-one (7) and 3-(dimethylamino)-8,9,10,11-tetrahydro-7H-cyclohepta[a]naphthalen-7-one (8) are reported. These compounds possess a cycloalkanone substructure that controls the extent of twisting of the carbonyl group. The six-membered ring in 7 forces the carbonyl group to be coplanar with the naphthalene ring, whereas the seven-membered ring in 8 induces a significant twist. Both have the substructure of PRODAN (6-propionyl-2-(dimethylamino)naphthalene, 1). Comparing the photophysical behavior of these compounds with that of PRODAN and 2,2-dimethyl-1-(4-methyl-1,2,3,4-tetrahydrobenzo[f]quinolin-8-yl)propan-1-one (3) indicates that PRODAN likely emits from a PICT excited state rather than from an O-TICT excited state.

Citing Articles

Fluorescence of Half-Twisted 10-Acyl-1-methyltetrahydrobenzoquinolines.

Abelt C, Day I, Zhao J, Pike R Molecules. 2024; 29(13).

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

Anderson R, Nagirimadugu N, Abelt C ACS Omega. 2019; 4(9):14067-14073.

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

Chen T, Lee S, Abelt C ACS Omega. 2019; 3(5):4816-4823.

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Electric dipole moments of the fluorescent probes Prodan and Laurdan: experimental and theoretical evaluations.

Vequi-Suplicy C, Coutinho K, Lamy M Biophys Rev. 2017; 6(1):63-74.

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Electrooptical Absorption Measurements (EOAM) Testify Existence of two Conformers of Prodan and Laurdan with Different Dipole Moments in Equilibrium Ground and Franck-Condon Excited State.

Nemkovich N, Detert H, Roeder N J Fluoresc. 2016; 26(5):1563-72.

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