O-Ethylation of phthalides with Meerwein's reagent followed by reaction of the ensuing salts with pyrrole, results in the formation of 5-alkoxy-5-phenyl dipyrromethane derivatives, which function as ready precursors of ortho-substituted 8-aryl BODIPY derivatives by reaction with borontrifluoride etherate, an overall process that can be carried out in a one-pot operation.

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.

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.

Urea‐bridged bis‐BODIPYs, a new family of chemically stable dyads can be efficiently obtained by a one‐pot synthetic Staudinger/aza‐Wittig ureation protocol from o‐azidomethyl meso‐phenyl BODIPYs. These derivatives outstand by a high absorption probability and excellent fluorescence emission in less polar media, which decreases in more polar media. This ureation protocol can also be employed in the conjugation of BODIPYs to amines. The cover artwork was kindly created by Guillermo Corrales. More information can be found in the Full Paper by J. C. López, J. Bañuelos, A. M. Gómez et al. on page 17511.

The cover picture shows two concise, complementary, protocols for the one‐pot, three‐component assembly of an alkyne‐ or azido‐carbohydrate, 8‐thiomethyl BODIPY, and either propargylamine or an azido boronic acid, respectively, which allow access to fluorescent carbohydrate–BODIPY hybrids. These carbohydrate–BODIPY hybrids display excellent photophysical and laser properties that relate to the spacer employed (amino group or aromatic ring). Details are discussed in the Short Communication by J. C. Lopez, J. Bañuelos, E. Peña‐Cabrera et al. on p. .