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

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

Журнал

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Вых. Данные

Год: 2018, Том: 2018, Номер: 26, Страницы: 3471-3480 Страниц : 10 DOI: 10.1002/ejoc.201800525

Ключевые слова

Redox chemistry; Electrochemistry; Cyclic voltammetry; Reduction; Radical ions

Авторы

Shundrina Inna K. ¹ , Odintsov Danila S. ¹ , Os'kina Irina A. ¹ , Irtegova Irina G. ¹ , Shundrin Leonid A. ^1,2

Организации

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Inst Organ Chem, Siberian Branch, Lab Electrochem Act Cpds & Mat, Acad Lavrentievs Ave, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Natl Res Univ, Dept Nat Sci, Novosibirsk 630090, Russia

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 degrees 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.

Shundrina I.K. , Odintsov D.S. , Os'kina I.A. , Irtegova I.G. , Shundrin L.A.
Synthesis, Electrochemical Reduction and Radical Anions of 2-[Bis(4-amino(nitro)phenyl)aminomethyl]-9H-thioxanthene-9-one Derivatives
European Journal of Organic Chemistry. 2018. V.2018. N26. P.3471-3480. DOI: 10.1002/ejoc.201800525 WOS Scopus РИНЦ OpenAlex

Опубликована online:	11 июл. 2018 г.
Опубликована в печати:	13 июл. 2018 г.

Web of science:	WOS:000438718400012
Scopus:	2-s2.0-85049964434
РИНЦ:	35782381
OpenAlex:	W2800025729

БД	Цитирований
Web of science	11
Scopus	8
OpenAlex	9