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- Title
1,2,5-Thiadiazolo[3,4-b]pyrazine-5,6-dicarbonitrile and derived porphyrazines: synthesis and electrochemical study.
- Authors
Mikhailov, Maksim S.; Hamdoush, Mahmoud; Islyaikin, Mikhail K.; Koifman, Oskar I.; Stuzhin, Pavel A.
- Abstract
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, [(TSN2PyzPA)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.
- Subjects
PYRAZINES; PORPHYRAZINES; CHEMICAL synthesis; ELECTROCHEMISTRY; MAGNESIUM
- Publication
ARKIVOC: Online Journal of Organic Chemistry, 2017, Vol 2017, p130
- ISSN
1551-7004
- Publication type
Article
- DOI
10.3998/ark.5550190.p010.103