One-Pot Synthesis of Brightly Fluorescent Mes2B-Functionalized Indolizine Derivatives via Cycloaddition Reactions.

ABSTRACT

Four new BMes2-functionalized indolizine derivatives (Mes = mesityl) have been prepared via the cycloaddition reaction between pyrido[2,1-a]isoindole (A) or pyrrolo[1,2-a]pyridine (B) and BMes2-containing alkynes. All four compounds are brightly blue or blue-green fluorescent with λ(em) = 428-495 nm and Φ = 0.27-0.68, depending on the substitution position of the BMes2 group. Experimental and TD-DFT computational data indicated that the primary electronic transitions responsible for the fluorescence of 1-4 are from HOMO to LUMO (π → π*) rather than charge transfer from N → B, which is in agreement with previous findings suggesting that the lone-pair on N is delocalized throughout the N-heterocycles.