Dramatic red-shifted fluorescence of [2.2]paracyclophanes with peripheral substituents attached to the saturated bridges

Abstract

A bridge-substituted [2.2]paracyclophane obtained from the organic solid state exhibits a dramatic red shift in fluorescence relative to [2.2]paracyclophane. A further red shift occurs upon alkylation of the pyridylcyclobutyl bridges. Our results demonstrate that [2.2]cyclophanes substituted at the bridge, despite not being attached via the extended π-system, are promising building blocks in the development of optical materials © 2009 American Chemical Society.