40227-17-6Relevant articles and documents
Subphthalocyanine azaanalogues – Boron(III) subporphyrazines with fused pyrazine fragments
Stuzhin, Pavel A.,Skvortsov, Ivan A.,Zhabanov, Yuriy A.,Somov, Nikolai V.,Razgonyaev, Oleg V.,Nikitin, Ivan A.,Koifman, Oskar I.
, p. 888 - 897 (2018/11/25)
Сyclotrimerization of pyrazine-2,3-dicarbonitrile and its phenyl substituted derivative in the presence of BCl3 in p-xylene leads to azaanalogues of subphthalocyanine dye. Non-substituted tripyrazinosubporphyrazine [Pyz3sPABCl] was formed only in trace amounts allowing only limited spectral study in solution. Hexaphenyl substituted derivative [Ph6Pyz3sPABCl] was isolated as chlorboron(III) complex and fully characterized by 1H, 13C, 11B NMR, IR, electronic absorption and emission spectroscopy, cyclovoltammetry and its structure was established by single crystal X-ray diffraction. Pyrazine fused subporphyrazines exhibit strong absorption bands at 300–310 and 530–550 nm. The phenyl substituted derivative [Ph6Pyz3sPABCl] has an additional intense charge transfer band at 390 nm and can be reversibly reduced at ?0.81 V (vs Ag/AgCl in MeCN). The influence of pyrazine rings on the geometrical and electronic structural features and spectral properties of subporphyrazine dye was also studied using DFT and TD DFT methods. Experimental and theoretical results evidence that fusion of pyrazine rings leads to stabilization of the frontier π-molecular orbitals and endows the macrocycle with enhanced electron deficiency. Pyrazine fused subporphyrazines can be considered as perspective dyes intensively absorbing in the 300–600 nm range for applications as n-type materials in organic electronics.
Efficient solvent-free synthesis of pyridopyrazine and quinoxaline derivatives using copper-DiAmSar complex anchored on SBA-15 as a reusable catalyst
Mohammadi, Marzieh,Bardajee, Ghasem Rezanejade,Pesyan, Nader Noroozi
, p. 1379 - 1386 (2015/09/01)
A catalytic system comprising mesoporous silica functionalized with Cu(II)-DiAmSar was synthesized. This was demonstrated as an efficient heterogeneous catalyst for the synthesis of biologically useful pyridopyrazine and quinoxaline heterocycles under solvent-free conditions. X-ray diffraction, transmission electron microscopy, N2 adsorption-desorption, Fourtier transformation infrared spectroscopy, and thermogravimetric analysis were used to characterize the catalyst and investigate the texture of SBA-15 during the grafting process.
Zirconium schiff-base complex modified mesoporous silica as an efficient catalyst for the synthesis of nitrogen containing pyrazine based heterocycles
Malakooti, Reihaneh,Bardajee, Ghasem Rezanejade,Mahmoudi, Hesamaldin,Kakavand, Nahale
, p. 853 - 861 (2013/08/23)
Zirconium Schiff-base complex modified SBA-15 was synthesized and characterized by powder X-ray diffraction (XRD), BET nitrogen adsorption-desorption methods, IR spectroscopy and thermogravimetric analysis. The XRD and BET analyses show that textural properties of SBA-15 were retained during the grafting procedure. The modified SBA was successfully applied as a heterogeneous catalyst for the synthesis of a library of nitrogen containing pyrazine based heterocycles in good to excellent yields in water media.
