Donor-acceptor, ferrocenyl substituted BODIPYs with marvelous supramolecular interactions

Abstract

A series of donor-acceptor ferrocenyl substituted BODIPYs have been designed and synthesized via palladium catalyzed Suzuki and Sonogashira coupling reactions. The UV-visible absorption results indicate intramolecular charge transfer from the ferrocene to the BODIPY. The fluorescence quantum yield was drastically reduced, where the ferrocenyl group was directly attached to the BODIPY. The single crystal X-ray structures of 1′, 2, 3, and 4 show marvelous supramolecular interactions. The crystal structure of 1′ shows an extensive hydrogen bonded 2D network, 2 shows sheet like structure, 3 shows zigzag packing along the a-axis, whereas 4 shows sheet like structure in which both the surfaces of the sheet are covered with the ferrocenyl group. © The Royal Society of Chemistry 2013.