Redox properties and radical anions of fluorinated 2,1,3-benzothia(selena)diazoles and related compounds

Redox properties and radical anions of fluorinated 2,1,3-benzothia(selena)diazoles and related compounds Научная публикация

Журнал

Journal of Physical Organic Chemistry
ISSN: 0894-3230

Вых. Данные

Год: 2010, Том: 23, Номер: 6, Страницы: 536-543 Страниц : 8 DOI: 10.1002/poc.1637

Ключевые слова

chalcogen-nitrogen pi-heterocycles; cyclic voltammetry; DFT calculations; electrochemical oxidation; electrochemical reduction; EPR spectroscopy; fluorinated pi-heterocycles; radical anions

Авторы

Vasilieva Nadezhda V. ² , Irtegova Irina G. ² , Gritsan Nina P. ^1,3 , Lonchakov Anton V. ^1,3 , Makarov Alexander Yu. ² , Shundrin Leonid A. ² , Zibarev Andrey V. ^2,3

Организации

1	(Данные Web of science) Russian Acad Sci, Inst Chem Kinet & Combust, Novosibirsk 630090, Russia
2	(Данные Web of science) Russian Acad Sci, Inst Organ Chem, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Univ, Dept Phys, Novosibirsk 630090, Russia

In comparison with 2,1,3-benzothia(selena)diazoles, electrochemical oxidation and reduction of their 4,5,6,7-tetrafluoro derivatives and a number of related compounds were studied by cyclic voltammetry. For nine examples of this class, the first reduction peaks are reversible and corresponding radical anions (RAs) are long-lived at 295 K in MeCN and especially in DMF. The oxidation peaks were irreversible and corresponding radical cations were not observed. Electrochemically generated RAs were characterized by EPR measurements and DFT calculations at the UB3LYP/6-31+G(d) level. The spin density distribution in the RAs is analyzed in connection with effects of S substitution by Se and/or H by F. The prospects of the studied RAs in the design and synthesis of magnetically active materials are discussed. Copyright (C) 2010 John Wiley & Sons, Ltd.

Vasilieva N.V. , Irtegova I.G. , Gritsan N.P. , Lonchakov A.V. , Makarov A.Y. , Shundrin L.A. , Zibarev A.V.
Redox properties and radical anions of fluorinated 2,1,3-benzothia(selena)diazoles and related compounds
Journal of Physical Organic Chemistry. 2010. V.23. N6. P.536-543. DOI: 10.1002/poc.1637 WOS Scopus РИНЦ

Опубликована online:	13 янв. 2010 г.
Опубликована в печати:	1 июн. 2010 г.

Web of science	WOS:000278636900009
Scopus	2-s2.0-77952903568
РИНЦ	15317780
OpenAlex	W2029683995