SYNTHESIS AND PHYSICOCHEMICAL PROPERTIES OF ((9H-(4,5-DIAZAFLUOREN)-9-YLIDENE)METHYL)ARYLENES

Abstract

The synthesis of ((9H-(4,5-diazafluorene)-9-ylidene)methyl)arylenes is presented and their physicochemical characteristics are studied by cyclic voltammetry and optical spectroscopy. The target compounds were synthesised from commercially available reagents in three steps using a combination of Suzuki-Miyaura cross-coupling and condensation reactions. It was found that the compounds had a low photoluminescence quantum yield in solution, and 9-(4-([2,2′-bithiophen]-5-yl)phenylidene)-9H-4,5-diazafluorene demonstrates aggregation-induced luminescence. The crystal structure of 9-(4-([2,2′-bithiophen]-5-yl)phenylidene)-9H-4,5-diazafluorene was solved by X-ray diffraction analysis. The single crystals of this compound have the elongated plate morphology and exhibit photoluminescence quantum yield of 5 %.