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

Авторы: Mikhailov M., Hamdoush M., Islyaikin M., Koifman O., Stuzhin P.
Журнал: ARKIVOC : free online journal of organic chemistry / Arkat-USA, Inc
Год издания: 2017
Издательство: Arkat-USA
Местоположение издательства: [Zurich], Switzerland
Первая страница: 130
Последняя страница: 139
DOI: 10.3998/ark.5550190.p010.103
Аннотация: 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.
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