Aggregation‐induced Emission Properties of Triphenylamine Chalcone Compounds

Abstract

Two triphenylamine chalcone derivatives 1 and 2 were synthesized through the Vilsmeier-Haack reaction and Claisen-Schmidt condensation reaction. Through ultraviolet absorption spectroscopy and uorescence emission spectroscopy experiments, it was con rmed that these two compounds exhibited good aggregation-induced emission (AIE) behavior in ethanol/water mixtures. The solvent effect test showed with the increase of the orientation polarizability of the solvent, the Stokes shift in the solvent of compound 1 and compound 2 shows a linear change trend. Through solid state uorescence test and universal density function theory (DFT), the existence of π-π stacking interaction in the solid state of the compound has been studied, resulting in weak uorescence emission. pH has no effect on the uorescence intensity of the aggregate state of excited state intramolecular proton transfer (ESIPT) molecules in an acidic environment, but greatly weakens its uorescence intensity in an alkaline environment. Cyclic voltammetry (CV) test shows that compound 1 was more prone to oxidation reaction than compound 2. The results of thermal stability test show that the thermal stability of compound 1 was better than that of compound 2, indicating that triphenylamine chalcone derivatives can improve the thermal stability of compounds by increasing the number of branches.

ESIPT‐based AIE luminogens: Design strategies, applications, and mechanisms

“…The representative examples of this type of ESIPT-based AIEgens are shown in Scheme 3S-W. Typically, the traditional AIE units, such as tetraphenylethene (TPE) [34,43,72,118,127,161,162,205,206] and triphenylamine, [74,174,180,207] are involved and combined with ESIPT units, of which the most are the first type in Scheme 2. In the third type of ESIPT-based AIEgens (Scheme 3X-AA), [55,60,76,108,196,208,209] the AIE and ESIPT units are overlapped and ligated via intramolecular hydrogen bonds.…”