Synthesis and aggregation-induced emission properties of α-perimidinyl 3-pyrrolyl BODIPY

Abstract

A new dye called the [Formula: see text]-perimidinyl 3-pyrrolyl BODIPY(PPyBODIPY) was synthesized readily by treating [Formula: see text]-formyl 3-pyrrolyl BODIPY with 1,8-diamino naphthalene in ethanol at reflux. The PPyBODIPY was thoroughly characterized and studied by HR-MS, 1D n 2D NMR, absorption, fluorescence and DFT/TDDFT techniques. The PPyBODIPY absorbs strongly in the 500-600 nm region and emits weakly in the region of 550–650 nm with low quantum yield. DFT optimized structure of PPyBODIPY revealed that the 3-pyrrolyl BODIPY unit was almost planar and the perimidinyl moiety was oriented at 78.88[Formula: see text] relative to appended pyrrole of 3-pyrrolyl BODIPY unit. The photophysical studies revealed that the PPyBODIPY acts as AIEgen and showed aggregation-induced emission behavior in a 60% H2O-THF mixture.