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

Abstract

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.