Design and synthesis of β-pyrrole functionalized ferrocenyl BODIPYs

Abstract

Ethynyl bridged ferrocenyl functionalized BODIPY 1 was synthesized via Sonogashira cross-coupling reaction. Tetracyanobutadiene (TCBD) and cyclohexa-2,5-diene-1,4-diylidene-expanded TCBD (DCNQ) incorporated ferrocenyl BODIPYs 2 and 3 were synthesized using [2 + 2] cycloaddition -retroelectrocyclization (CA-RE) reaction, in good yields. BODIPYs 2 and 3 were obtained by reacting BODIPY 1 with strong electron acceptors tetracyanoethylene (TCNE) and tetracyanoquinodimethane (TCNQ) respectively. The electronic absorption spectra and theoretical calculations have been performed using the UV-visible spectrophotometer and density functional theory at B3LYP/6-31+G** level of theory.