Highly emissive D-A-π-D type aggregation-induced emission (AIE) or aggregation-induced emission enhancement (AIEE)-active benzothiadiazole derivatives with contrasting mechanofluorochromic features

Abstract

Mechanochromic luminophors with strong solid-state emission are promising candidates for high-contrast mechanochromic luminescence materials. Meanwhile, mechanically responsive luminogenic molecules with tricolor switching are highly desirable but are seldom reported. In this work, three anthracene-based donor-acceptor-π-donor (D-A-π-D) type benzothiadiazole derivatives were designed and synthesized. These luminogens showed remarkable aggregation-induced emission (AIE) or aggregation-induced emission enhancement (AIEE) effect. Furthermore, these luminogens exhibited bright and different solid state fluorescence involving yellow-green, yellow and orange colors, and the fluorescence of their solids could be effectively regulated by mechanical grinding. For luminogen 1, its solid displayed reversible two-color mechanofluorochromic property. As for luminogens 2 and 3, their solids displayed fluorescent colors change from yellow to yellow-green upon slight grinding, and the yellow-green light-emitting solids were converted into orange fluorescent solids after heavy grinding, demonstrating interesting three-color mechanofluorochromism features.

Keywords: Aggregation-induced emission; Aggregation-induced emission enhancement; Anthracene; Benzothiadiazole; Different solid state fluorescence; Three-color mechanofluorochromism.