Donor-acceptor meso-alkynylated ferrocenyl BODIPYs: Synthesis, structure, and properties

Abstract

meso-Alkynylated ferrocenyl BODIPYs (3-6) with varying conjugation length have been designed, and synthesized using the palladium catalyzed Sonogashira cross-coupling reaction of meso-chloro BODIPY with the corresponding ferrocenylethynes. These BODIPYs have been designed to improve the electronic communication between the donor ferrocene, and the acceptor BODIPY. The photonic and electrochemical properties indicate charge transfer (CT) from the ferrocene to the BODIPY. Single crystal X-ray structures of 2′, 3, and 6 show interesting supramolecular interactions. Computational studies were used to study the electronic structure of the BODIPYs. © 2013 The Royal Society of Chemistry.