Two bis-bromo substituted imidazo-[1,5-a]-pyridine derivatives IMPY1 and IMPY2 were synthesized from a 2:1:2 mixture of ortho/meta-bromobenzaldehyde, 2-cyanopyridine and ammonium acetate. The compounds IMPY1 and IMPY2 exhibit blue fluorescence in both THF and methanol solution and their highly fluorescent nature is revealed by the quantum yields ΦF ranging from 9.3 to 10.4%. The crystal structure of the compounds are stabilized by various weak, non-classical hydrogen bonds viz. C−H⋯N, C−H⋯Br and C−H⋯π as well as type II interhalogen and C−Br⋯π halogen bonds. The supramolecular features and electronic property of these compounds have been thoroughly analyzed with the aid of DFT, TD-DFT and molecular electrostatic potential (MEP) analyses.