Furan-based diketopyrrolopyrrole chromophores: Tuning the spectroscopic, electrochemical and aggregation-induced fluorescent properties with various intramolecular donor-acceptor spacers

Abstract

A family of furan-based diketopyrrolopyrrole chromophores, which comprise different donor or acceptor spacers, was synthesized by classic Suzuki-Miyaura reactions between dibrominated diketopyrrolopyrrole intermediate and five substituted aromatic boronic acids. They have the same π-extended unit and different pyridyl, thienyl and triarylamino tails with various intramolecular donor-acceptor spacers. Furthermore, absorption and emission spectral studies reveal that all dyes show extraordinarily large molar absorption coefficients (εmax = 22 400–120 000 L mol−1 cm−1) and high luminescence quantum yields (Φs = 27–88%). Moreover, the TGA studies indicate that the triarylamino-extended compounds have excellent thermal stabilities. A systematical investigation has been carried out, including energy gap correlation among optical, electrochemical and computational data. All the targeted chromophores exhibit potential applications in luminescent materials and optoelectronic devices.