BOPYIN-anil and BOPYIN-boranil complex: Synthesis, spectroscopic properties and ESIPT process

Abstract

Two BOPYIN dyes (W-1 and W-2) were synthesized, and their structural and photophysical properties were investigated. The absorption bands of both dyes located at ca. 350 and 500 nm in diverse solvents. The absorption profiles are a linear combination of those of the BOPYIN core and the boranil or anil subunits. Their emission spectra were observed at ca. 565 and 540 nm with 14.2% and 77% quantum yield in CHCl3, respectively. The absorption, excitation and emission spectra for both dyes confirm that the boranil or anil moieties could be used as an input energy antenna for cascade energy transfer to the fluorescent BOPYIN residue at 540 nm. Subsequently, ESIPT process of W-1 is fast and more likely to occur in non-polar solvent investigated by DFT calculation.