Synthesis and photophysical properties of models for twisted PRODAN and dimethylaminonaphthonitrile

Brittany N Davis; Christopher J Abelt

doi:10.1021/jp046050y

Synthesis and photophysical properties of models for twisted PRODAN and dimethylaminonaphthonitrile

J Phys Chem A. 2005 Feb 24;109(7):1295-8. doi: 10.1021/jp046050y.

Authors

Brittany N Davis¹, Christopher J Abelt

Affiliation

¹ Department of Chemistry, College of William and Mary, Williamsburg, Virginia 23187-8795, USA.

PMID: 16833443
DOI: 10.1021/jp046050y

Abstract

The synthesis and photophysical properties of 7-cyano-3,4-dihydro-2H-1,4-ethano-benzo[g]quinoline and 3,4-dihydro-2H-1,4-ethano-7-propionyl-benzo[g]quinoline are reported. These compounds possess a quinuclidine substructure that locks the tertiary amino group perpendicular to the naphthalene ring. Their excited states are models for the twisted excited states of 2-(dimethylamino)-6-naphthonitrile (DMANN) and 6-propionyl-2-(dimethylamino)naphthlene (PRODAN). In contrast to DMANN and PRODAN, the fluorescence of these twisted derivatives is strongly deactivated in polar solvents. Neither DMANN nor PRODAN likely emit from TICT excited states.