Photochromism and Fluorescence Switch of Furan-Containing Tetraarylethene Luminogens with Aggregation-Induced Emission for Photocontrolled Interface-Involved Applications

Abstract

It is extremely challenging to design photocontrolled molecular switches with absorption and fluorescence dual-mode outputs that are suited for a solid surface and interface. Herein, we report a group of furan-containing tetraarylethene derivatives with unique photophysical behavior of aggregation-induced emission (AIE) and distinct photochemical reaction-triggered photochromic behaviors by combining a photoactive furan or benzofuran group and an AIE-active triphenylethene molecule. The introduction of a furyl or benzofuryl group into the AIE luminogen endows the molecules with significant reversible photochromism and solid-state fluorescence. The coloration and decoloration of these molecules can be switched by respective irradiation of UV and visible light in a reversible way, and the photochromic changes are accompanied by a switch-on and switch-off of the solid-state fluorescence. It is revealed that the photocontrolled cyclization and cycloreversion reactions are responsible for the reversible photochromism and fluorescence switching based on experimental data and theoretical analysis. Both the position and conjugation of the introduced photoactive units have significant influence on the color and strength of the photochromism, and the simultaneous occurrence of photoinduced fluorescence change in the solid state is perfectly suited for surface-involved applications. The demonstrations of dual-mode signaling in photoswitchable patterning on a filter paper and anti-counterfeiting of an anti-falsification paper strongly highlight the unique advantage of these photochromic molecules with an aggregation-induced emission characteristic in various practical applications. This work proposes a general strategy to design photochromic molecules with AIE activity by introducing photoactive functionals into an AIEgen and demonstrates incomparable advantage in dual-mode signaling and multifunctional applications of these molecules.