1,2,5-Thiadiazolo[3,4-b] pyrazine-5,6-dicarbonitrile and derived porphyrazines: synthesis and electrochemical study

被引：6
|
作者：
Mikhailov, Maksim S. [1 ]
Hamdoush, Mahmoud [1 ]
Islyaikin, Mikhail K. [1 ]
Koifman, Oskar I. [1 ]
Stuzhin, Pavel A. [1 ]
机构：
[1] Ivanovo State Univ Chem & Technol, Res Inst Macroheterocycles, RF-153460 Ivanovo, Russia
来源：
ARKIVOC | 2017年
基金：
俄罗斯科学基金会;
关键词：
1,2,5-Thiadiazolo[3.4-b] pyrazine-2,3-dicarbonitrile; porphyrazines; magnesium(II); indium(III) complexes; UV-vis spectra; electrochemistry; COMPLEXES; RINGS;
D O I：
10.3998/ark.5550190.p010.103
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1,2,5-Thiadiazolo[3,4-b] pyrazine-5,6-dicarbonitrile, obtained by reaction of 5,6-diaminopyrazine-2,3-dicarbonitrile with SOCl2, exhibits strongly electron-deficient properties and easily forms reduced species (the reduction potentials -0.01 and -1.02 V in MeCN vs Ag/AgCl). Template cyclotetramerization in the presence of Mg butoxide in n-butanol and with indium(III) chloride in 1,2,4-trichlorobenzene affords the corresponding complexes of tetrakis(1,2,5-thiadiazolo[3',4':5,6] pyrazino)[2,3-b, g, l, q] porphyrazine, [(TSN(2)PyzPA)M] (M = Mg(H2O), InCl). The Mg(II) complex is characterized by a Q-band at 657 and a Soret band at 370 nm (in DMSO) and shows three reduction processes at -0.38, -0.83 and -1.21 V vs Ag/AgCl in DMSO.
引用
收藏
页码：130 / 139
页数：10
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