Acenaphthylene-fused cyclo[8]pyrroles with intense near-IR-region absorption bands.
Chemistry
; 19(41): 13970-8, 2013 Oct 04.
Article
em En
| MEDLINE
| ID: mdl-24038591
ABSTRACT
An acenaphthylene-fused cyclo[8]pyrrole was synthesized by using an oxidative coupling reaction of the corresponding 2,2'-bipyrrole. Two conformational isomers 1 a and 1 b were isolated, and their molecular structures were elucidated by X-ray crystallographic studies. The less-polar and lower-symmetry 1 b isomer can be converted into the 1 a isomer through a thermal ring flip. Application of the perimeter model developed by Michl to magnetic circular dichroism spectroscopic data and theoretical calculations demonstrate that there is a marked redshift of the near-IR absorption maxima relative to cyclo[8]isoindole because there is a significant stabilization of the LUMO due to the differing effects of a fused ring expansion with acenaphthylene and benzene moieties on the frontier πâ
molecular orbitals.
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Coleções:
01-internacional
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MEDLINE
Idioma:
En
Revista:
Chemistry
Ano de publicação:
2013
Tipo de documento:
Article