tert-Butyl substituted hexaazasubphthalocyanine: Synthesis, isolation of C1 and C3 regioisomers and their spectral-luminescence study

Autor:	Oskar I. Koifman, Alexey S. Panteleev, Ivan A. Skvortsov, Pavel A. Stuzhin
Rok vydání:	2021
Předmět:	Tert butyl 010405 organic chemistry chemistry.chemical_element General Chemistry 010402 general chemistry 01 natural sciences Boron trichloride Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Structural isomer Luminescence Boron
Zdroj:	Journal of Porphyrins and Phthalocyanines. 25:282-288
ISSN:	1099-1409 1088-4246
Popis:	By cyclotrimerization of tert-butyl substituted pyrazine-2,3-dicarbonitrile in the presence of boron trichloride, two positional isomers ([Formula: see text] and [Formula: see text] symmetry) of the corresponding boron(III) tripyrazinosubporphyrazines were first obtained and efficiently separated by column chromatography. The new compounds were characterized by MALDI mass-spectrometry, UV-visible and 1H NMR spectroscopy. A Q-band in the electronic absorption spectra for both fractions was observed at [Formula: see text]530 nm, which is typical for tripyrazinosubporphyrazines. The fluorescence quantum yield for the regioisomer with lower symmetry ([Formula: see text] is 1.5 times higher than for the more symmerical [Formula: see text] species ([Formula: see text] = 0.37 and 0.28, respectively). Comparative spectrophotometric study of the basic properies reveals that hexaaza substitution in benzene rings of tert-butyl substituted subphthalocyanine decreases the basic properties of meso-nitrogen atoms.
Databáze:	OpenAIRE
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