The oxasmaragdyrins containing one five membered heterocycle such as pyrrole, thiophene and furan in place of one of the meso-phenyl group were synthesized by acid-catalyzed oxidative coupling reaction of meso-heterocycle substituted dipyrromethane with 16-oxatripyrrane in the presence of catalytic amountof trifluoroacetic acid followed by oxidation with DDQ. The smaragdyrin macrocycles containing one fivemembered heterocycle at meso-position were characterized by HR-MS and detailed 1D and 2D NMR studies. The absorption and fluorescence studies revealed that the presence of five membered heterocycle at mesoposition of smaragdyrin resulted in bathochromic shifts in absorption and emission bands with slight reduction in quantum yields compared to smraragdyrin macrocycle containing six membered meso-phenyl groups. Theelectrochemical studies revealed that the meso-heterocycle smaragdyrins are electron deficient compared to meso-phenyl smaragdyrins.