Direct Access to Pyrrolyltripyrrins and Calixsmaragdyrin from SAr Reactions on α,α'-Dibromotripyrrins with Pyrroles or Indoles.

Linear π-conjugated oligopyrroles are attractive precursors for the synthesis of expanded porphyrinoids, chemosensors, and supramolecular motifs. We demonstrate a new method for the synthesis of a set of linear pyrrolyltripyrrins and dipyrrolyltripyrrins through a regioselective SAr reaction on α,α'-dibromotripyrrins using various pyrroles or indoles. A representative calixsmaragdyrin was prepared via the 2-fold SAr reaction between α,α'-dibromotripyrrin and dipyrromethene through a convergent [3 + 2] strategy.

Red-to-Near-Infrared Emitting PyrrolylBODIPY Dyes: Synthesis, Photophysical Properties and Bioimaging Application.

Near-infrared (NIR) fluorophores with characteristics such as deep tissue penetration, minimal damage to the biological samples, and low background interference, are highly sought-after materials for in vivo and deep-tissue fluorescence imaging. Herein, series of 3-pyrrolylBODIPY derivatives and 3,5-dipyrrolylBODIPY derivatives have been prepared by a facile regioselective nucleophilic aromatic substitution reaction (S Ar) on 3,5-halogenated BODIPY derivatives (3,5-dibromo or 2,3,5,6-tetrachloroBODIPYs) with pyrroles. The installation of a pyrrolic unit onto the 3-position of the BODIPY chromophore leads to a dramatic red shift of both the absorption (up to 160 nm) and the emission (up to 260 nm) in these resultant 3-pyrrolylBODIPYs with respect to that of the BODIPY chromophore.