Synthesis and physicochemical properties of 2,7-di(thiophen-2-yl)-9H-(4,5-diazafluoren)-9-one
D. A. POTAPOV1,2, A. A. SONINA1, C. S. BECKER1, M. S. KAZANTSEV1
1Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Brach of the Russian Academy of Sciences, Novosibirsk, Russia
2Novosibirsk State University, Novosibirsk, Russia
Keywords: 4,5-diazafluorene, cross-coupling, photoluminescence, electropolymerisation
Abstract
2,7-Di(thiophen-2-yl)-9H-(4,5-diazafluoren)-9-one (TDAFO) was synthesised and its crystal structure, optical and electrochemical properties were studied. The target compound was obtained using the Stille reaction from 2-(tri(n-butylstannyl)thiophene and 2,7-dibromo-4,5-diazafluoren-9-one. Using X-ray diffraction analysis, the crystal structure of TDAFO was solved, and the formation of weak π-stacking interactions, C-H…N and C-H…O hydrogen bonds was revealed. The oxidation and reduction potentials of TDAFO were evaluated by cyclic voltammetry, and the possibility of TDAFO electropolymerisation on conductive coatings was demonstrated. The optical properties of both the monomer and the polymer obtained by electrochemical polymerisation were studied. The photoluminescence quantum yield of TDAFO was determined to be 7 % in solution and 13 % in the crystalline form.
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