Synthesis and Physicochemical Properties of ((9H-(4,5-Diazafluoren)-9-ylidene)methyl)arylenes
D. S. CHESHKINA, C. S. BECKER, A. A. SONINA, M. S. KAZANTSEV
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russia
Keywords: 4,5-diazafluorenylidenes, condensation, photoluminescence, crystallization, aggregation-induced luminescence
Abstract
The synthesis of ((9 H -(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)-9 H -4,5-diazafluorene demonstrates aggregation-induced luminescence. The crystal structure of 9-(4-([2,2'-bithiophen]-5-yl)phenylidene)-9 H -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 %.
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