Synthesis and photophysical properties of novel phthalocyanine–perylenediimide–phthalocyanine triad and phthalocyanine–perylenediimide dyads

Abstract

A series of novel multi-component chromophores, one phthalocyanine–perylenediimide–phthalocyanine triad and two phthalocyanine–perylenediimide dyads, were synthesized by covalent linkage between phthalocyanines and perylene-3,4,9,10-bis(dicarboximide) at the bay position of perylene core in one condensation reaction. The photophysical properties of the dyes were presented with wider light absorption from 300 to 800 nm and discussed by interpretation and correlations with previous dyes. Density functional theory at the B3LYP level with 6-31G(d) was performed for geometry and energy optimization. Furthermore, a substitution and elimination reaction at the perylene bay position by using 1,8-diazabicyclo[5,4,0]undec-7-ene as catalyst was performed and its probable mechanism discussed.