Polyanils and Polyboranils: Synthesis, Optical Properties, and Aggregation-Induced Emission

Abstract

A first series of polyanils were synthesized by a simple condensation between either isomers of phenylenediamine derivatives or 1,3,5-benzenetriamine and 4-(diethylamino)salicylaldehyde, while a second series resulted from the condensation between 4,6-dihydroxyisophthalaldehyde or 2,5-dihydroxyterephthalaldehyde and differently substituted anilines. All these polyanils showed good chelating abilities toward trivalent boron fragments such as BF₂ or BPh₂ to yield the corresponding boranils. The optical properties of these novel fluorophores have been studied both in solution and in the solid-state and show emission wavelengths covering the entire visible spectrum and near-infrared (NIR), depending on molecular structure, substitution, and environment. While faintly fluorescent in solution in their molecular state, some polyanils show typical aggregation-induced emission (AIE) behavior upon addition of increasing amounts of water in THF solution, leading to a sizable enhancement of fluorescence intensity.