Synthesis and Luminescence Properties of (Z)-2-(Difluoroboryl)-3-(quinolin-2-ylmethylidene)-2,3-dihydro-1H-benzo[5,6][1,4]dioxino[2,3-f]isoindol-1-one, a New Unsymmetrical BODIPY Analogue.

Autor:	Nabasov, A. A., Rumyantseva, T. A., Galanin, N. E., Baklagin, V. L., Abramova, M. B., Abramov, I. G.
Předmět:	FLUORESCENCE yield STAINS & staining (Microscopy) LUMINESCENCE STOKES shift BUTANOL
Zdroj:	Russian Journal of Organic Chemistry; Apr2024, Vol. 60 Issue 4, p638-644, 7p
Abstrakt:	The reaction of dibenzo[b,e][1,4]dioxine-2,3-dicarbonitrile with sodium butoxide in butyl alcohol, followed by treatment with nitric acid, gave 1H-benzo[5,6][1,4]dioxino[2,3-f]isoindole-1,3(2H)-dione, which was brought into the condensation with quinaldine to obtain (E,Z)-3-(quinolin-2-ylmethylidene)-2,3-dihydro-1H-benzo[5,6][1,4]dioxino[2,3-f]isoindol-1-one. Treatment of the latter with BF3·Et2O in the presence of tri-ethyl-amine in toluene afforded a new unsymmetrical BODIPY analogue, (Z)-2-(difluoroboryl)-3-(quinolin-2-ylmethylidene)-2,3-dihydro-1H-benzo[5,6][1,4]dioxino[2,3-f]isoindol-1-one. The product showed luminescence in solution with a Stokes shift of 36 nm and a high relative fluorescence quantum yield (φ = 0.72). The obtained experimental data were supported by DFT and TD-DFT calculations. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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