A Straightforward Strategy for the Preparation of Diverse BODIPY Functionalized with Polyamines and Polyoxyethylenes

Novel derivatives of 4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indacene (BODIPY) functionalized at the meso-position with polyamines and polyoxyethylenes were synthesized through single-step condensation of fluorogenic 8-CH2Cl-substituted BODIPY and corresponding amines. The systematic spectroscopic characterization (UV-Vis, fluorescence) of stable in storage dyes bearing polyoxyethylene substituents was carried out. One compound showed promise for UV-Vis and "off-on" fluorescence Cu2+ detection in acetonitrile solutions. The ligand detects Cu2+ ions selectively in the presence of eighteen different alkaline earth metal cations.