Novel pyrromethene dyes with N-ethyl carbazole at the meso position: a comprehensive photophysical, lasing, photostability and TD-DFT study

Abstract

Two novel BODIPY (pyrromethene, PM) dyes containing N-ethyl carbazole at the meso position are synthesized and their photophysical properties in different solvents and the photochemical stabilities and laser performances in n-heptane are investigated. The n-heptane solution of the dyes was used as a gain medium in a constructed narrow band dye laser, pumped by a Q-switched (10 Hz) frequency-doubled (532 nm) Nd:YAG laser and the results gave enhanced photo stabilities and similar peak efficiencies of the synthesized dyes as compared to parent dye PM567. When substituted at the meso position with N-alkyl carbazole, photostability is found to be increased in comparison to PM567, and also when substituted at 2- and 6-positions with a benzyl group instead of an ethyl group along with N-ethyl carbazole at the meso position, the photo stability is further increased in n-heptane. A comprehensive study on structural, photophysical and electronic properties of dyes by means of DFT and TD-DFT in the solvents of various polarities has revealed remarkable characteristics of the BODIPY chromophore.