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Synthesis and Fluorescence of a Series of Multichromophoric Acenaphthenyl Compounds.
- Source :
-
Journal of Organic Chemistry . 3/4/2005, Vol. 70 Issue 5, p1844-1852. 9p. 7 Diagrams, 2 Graphs. - Publication Year :
- 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 in compounds containing identical stereochemical arrangements of adjacent acenaphthenyl groups is excimer fluorescence observed following photoexcitation. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 70
- Issue :
- 5
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 16333495
- Full Text :
- https://doi.org/10.1021/jo047899d