Synthesis and fluorescence of a series of multichromophoric acenaphthenyl compounds.
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 in compounds containing identical stereochemical arrangements of adjacent acenaphthenyl groups is excimer fluorescence observed following photoexcitation.
Chen
Ming
M
School of Chemistry, The University of Melbourne, Victoria 3010, Australia.
Ghiggino
Kenneth P
KP
Thang
San H
SH
White
Jonathan
J
Wilson
Gerard J
GJ
D000073:Acenaphthenes / Q000138:chemical synthesis* / Q000737:chemistry; D005609:Free Radicals / Q000138:chemical synthesis / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D013050:Spectrometry, Fluorescence; D013237:Stereoisomerism
D000073:Acenaphthenes; D005609:Free Radicals