Solvent-Sensitive Emitting Urea-Bridged bis-BODIPYs: Ready Access by a One-Pot Tandem Staudinger/Aza-Wittig Ureation

Herein we describe the synthesis, and computationally aided photophysical characterization of a new set of urea-bridged bis-BODIPY derivatives. These new dyads are efficiently obtained by a one-pot tandem Staudinger/aza-Wittig ureation protocol, from easily accessible meso-phenyl ortho-azidomethyl BODIPYs. These symmetric bis-BODIPYs outstand by a high absorption probability and excellent fluorescence and laser emission in less polar media. Nevertheless, this emission ability decreases in more polar media, which is ascribed to a light-induced charge-transfer from the urea spacer to the dipyrrin core, a process that can be modulated by appropriate changes in the substitution pattern of the BODIPY core. Furthermore, this ureation protocol can also be employed for the direct conjugation of our BODIPY-azides to amine-containing compounds, thus providing access to fluorescent non-symmetric ureas.Peer Reviewe

Convenient access to carbohydrate - BODIPY hybrids by two complementary methods involving one-pot assembly of >clickable> BODIPY dyes

Two complementary one-pot, three component synthetic strategies based on copper(I)-catalyzed azide - alkyne cycloadditions (CuAAC) have been developed, which allow the efficient assembly of glycosyl-derived alkynes or azides with highly fluorescent boron-dipyrromethene (BODIPY) cores containing azido or alkyne moieties, respectively. The resulting carbohydrate - BODIPY derivatives display excellent photophysical and laser properties that relate to the spacer (amino group or aromatic ring) employed in each of the synthetic protocols.Peer Reviewe