Donor acceptor type ferrocene substituted aza-BODIPYs: Synthesis, optical and electrochemical studies

Abstract

Two ferrocene substituted aza-BODIPYs and their corresponding aza-dipyrrins were synthesized and studied. All the compounds were characterized by HRMS, NMR, IR, absorption spectroscopy and cyclic voltammetry techniques. Absorption spectra indicated intramolecular electron transfer from the ferrocene to the aza-BODIPY core. The X-ray crystal structure of 1,7-bisferrocenyl-aza-BODIPY suggested moderate interactions between the ferrocene moieties and aza-BODIPYs core. Ferrocenyl-aza-BODIPYs were non-emissive due to electron transfer from ferrocene moieties to boron aza-dipyrrin core. However the emission of these compounds was dramatically enhanced by oxidizing the ferrocene moieties to ferrocenium ions, which prevents electron transfer between these moieties. Cyclic voltammetry studies suggested that aza-BODIPYs were easier to be reduced as compared to their corresponding aza-dipyrrins.