Synthesis, Electrochemical Reduction and Radical Anions of 2-[Bis(4-amino(nitro)phenyl)aminomethyl]-9H-thioxanthene-9-one Derivatives

Inna K. Shundrina, Danila S. Odintsov, Irina A. Os'kina, Irina G. Irtegova, Leonid A. Shundrin

Результат исследования: Научные публикации в периодических изданияхстатья

2 Цитирования (Scopus)

Аннотация

2-[Bis(4-amino(nitro)phenyl)aminomethyl]-9H-thioxanthene-9-ones and their S-oxide derivatives have been synthesized, and their electrochemical reduction (ECR) in N,N-dimethylformamide (DMF) and MeCN has been studied by cyclic voltammetry (CV). The thioxanthene-9-one group [Th(O)S] and thioxanthene-9-one S-dioxide group [Th(O)SO2] determine the first one-electron peak potentials of 2-[bis(4-aminophenyl)aminomethyl]-9H-Th(O)S/Th(O)SO2. The first peak potentials of the corresponding dinitro compounds are determined by the ratio of reduction potentials of bis(4-nitrophenyl)amino and 9H-thioxanthene-9-ones moieties. Radical anions (RA) of the synthesized compounds have been obtained by ECR in DMF and MeCN and characterized by EPR spectroscopy together with DFT calculations at the (U)B3LYP/6-31 + G/PCM level of theory. Th(O)S and Th(O)SO2 groups are thermally stable up to 270 °C. The synthesized 2-[bis(4-aminophenyl)aminomethyl]-9H-Th(O)S/Th(O)SO2 are electrochemically active monomers for subsequent synthesis of the corresponding electroactive polyimides with thioxanthene-9-one based pendant groups for their applications in the design of nonvolatile memory storage devices. The pendant groups are characterized by low redox potentials and reversibility towards electron transfer.

Язык оригиналаанглийский
Страницы (с-по)3471-3480
Число страниц10
ЖурналEuropean Journal of Organic Chemistry
Том2018
Номер выпуска26
DOI
СостояниеОпубликовано - 13 июл 2018

Fingerprint Подробные сведения о темах исследования «Synthesis, Electrochemical Reduction and Radical Anions of 2-[Bis(4-amino(nitro)phenyl)aminomethyl]-9H-thioxanthene-9-one Derivatives». Вместе они формируют уникальный семантический отпечаток (fingerprint).

  • Цитировать