Design of Aurone-Based Dual-State Emissive (DSE) Fluorophores

Chemistry. 2023 May 11;29(27):e202300356. doi: 10.1002/chem.202300356. Epub 2023 Mar 22.

Abstract

The development of dual-state emissive (DSE) fluorophores, i. e. organic molecules showing balanced emission in both solution and as molecular solids, has recently become an emerging approach in material science, biology, sensing, and optoelectronics. However, the majority of existing DSE fluorophores represents structural modifications of the scaffolds known for their aggregation-induced emission (AIE) properties, e. g., tetraphenylethylenes (TFE), triphenylamines (TFA), and others. In this study, we introduce aurones as an easily accessible scaffold for the construction of DSE fluorophores and describe the main design principles allowing to achieve the balanced emission in both solution and solid state. Herein, we present the solid-state fluorescence in a systematic series of aurone derivatives for the first time. We propose that the newly found DSE properties of aurones in combination with their established biological activity can be applied efficiently in biomedical studies and diagnostic tools.

Keywords: O-heterocycles; dual-state emissive fluorophores; photochemistry; photophysics; solid-state emission.