Synthesis and characterization of methoxy- or cyano-substituted thiophene/phenylene co-oligomers for lasing application

As new candidates of thiophene/phenylene co-oligomer (TPCO) species, 5,5′′-bis(4′-methoxy-[1,1′-biphenyl]-4-yl)-2,2′:5′,2′′-terthiophene (BP3T-OMe) and 4′,4′′′-([2,2′:5′,2′′-terthiophene]-5,5′′-diyl)bis(([1,1′-biphenyl]-4-carbonitrile)) (BP3T-CN) were synthesized for lasing applications. Although most unsubstituted TPCO species crystallize in monoclinic form, BP3T-OMe and BP3T-CN crystallized in orthorhombic and triclinic forms, respectively. Since the unsubstituted species, 5,5′′-bis(4-biphenylyl)-2,2′:5′,2′′-terthiophene (BP3T), shows unique and superior lasing performance in single crystals, the newly synthesized BP3T-OMe and BP3T-CN have possibilities to show different or improved optoelectronic characteristics. Amplified spontaneous emission (ASE) and optically pumped lasing were observed from both of the single crystals based on their well-shaped crystalline cavity and high group refractive index values of 3.7–5.3 for excellent light confinement. The lasing threshold for the BP3T-OMe crystal was lower than that for the BP3T-CN crystal, which was attributed to their different molecular orientation, standing in the former and inclining in the latter.