Journal article

Synthesis and fluorescence of a series of multichromophoric acenaphthenyl compounds

M Chen, KP Ghiggino, SH Thang, J White, GJ Wilson

JOURNAL OF ORGANIC CHEMISTRY | AMER CHEMICAL SOC | Published : 2005

Abstract

A novel free radical trapping reaction based on a stepwise radical reversible addition-fragmentation mechanism has been utilized to synthesize a series of acenaphthenyl dimers and trimers. The synthetic procedure involves the reaction of acenaphthylene with dithiobenzoate compounds (S=C(Ph)-SR) in the presence of a free radical initiator followed by reduction of the dithiobenzoyl end group with tributyltin hydride. Stereoisomers of the compounds have been isolated and their structures determined by proton NMR and X-ray crystallography. The solution fluorescence of the compounds has been characterized to reveal the requirements for intramolecular excimer (excited-state dimer) formation. Only ..

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