Ferrocenyl aza-dipyrromethene and aza-BODIPY: Synthesis and properties

Abstract

A series of ferrocenyl substituted tetraphenylazadipyrromethane and Aza-BODIPY were designed and synthesized by the Pd-catalyzed Sonogashira cross-coupling reaction. The effect of the pyrrolic substituents on photophysical and electrochemical properties was explored. The results show substantial electronic communication between the ferrocene unit, and Aza-BODIPY core. The aza-dipyromethane and aza-BODIPY 3–6 are non-emissive in nature and their absorption maxima exhibit red shifted absorption compared to unsubstituted azabodipy. The computational calculation on Aza-BODIPY 5 and 6 was performed, which reveals that electron density transfers from ferrocene (donor) to azabodipy (acceptor) core and the photophysical properties are in good agreement with the computational data. © 2016 Elsevier B.V.