Substituent effects on opticalproperties of pyrrolizine-fused BOPYIN.

Three new pyrrolizine-fused BOPYINs (DAB-H, DAB-OMe, DAB-ester) have been reported in 26-35% yield. The relationship between structures and optical spectra was investigated, which all the compounds show large Stokes Shift (3146-3884 cm-1) and high quantum yield (up to 99%) in solvents. Among these dyes, the decoration of electron donating/withdrawing groups on indole, pyrrole and pyrrolizine units has a significant impact on optical properties, especially emission spectra. The results suggested that electron withdrawing group on pyrrole and pyrrolizine units has hypsochromic shift on emission spectra (DAB-H, DAB-OMe, DAB-ester versus DAB-1,4,5). The optimized structure, electron distribution on frontier molecular orbital, energy gap and simulated stick spectra of DABs are discussed by Density Functional Theory (DFT) calculation. We claim the agreement between the experimental and theoretical absorption spectra.