Synthesis, optical and electrochemical properties of novel meso-triphenylamine-BODIPY dyes with aromatic moieties at 3,5-positions

Abstract

Four novel symmetrical D-A-D type of BODIPY dyes with triphenylamine in the meso-position and electron-donor aromatic moieties in the 3,5-positions were efficiently synthesized and characterized. 3,5-positions substituted aromatic groups rouse intensive intramolecular charge transfer (ICT), led to extended and red-shifted absorption bands to the near-infrared region. All these BODIPY dyes exhibit broad absorption bands range from 250 nm to nearly 800 nm both in CH2Cl2 solution and in thin films and high extinction coefficients (48,700 M−1 cm−1). The emission spectra of these dyes were up to near-infrared regions peak at ∼709 nm. The LUMO and HOMO energy levels of them are calculated to be −5.2 and −3.5 eV, respectively, by cyclic voltammetry and absorption spectra.