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  • Does PRODAN possess an O-TICT excited state? Synthesis and properties of two constrained derivatives.

Does PRODAN possess an O-TICT excited state? Synthesis and properties of two constrained derivatives.

The journal of physical chemistry. A (2010-03-25)
Renata K Everett, H A Ashley Nguyen, Christopher J Abelt
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
N,N-Dimethyl-6-propionyl-2-naphthylamine, BioReagent, suitable for fluorescence, ≥98.0% (HPLC)