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Preparation of Multi-Spin Systems: A Case Study of Tolane-Bridged Verdazyl-Based Hetero-Diradicals Научная публикация

Журнал European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690
Вых. Данные Год: 2020, Том: 2020, Номер: 13, Страницы: 1996-2004 Страниц : 9 DOI: 10.1002/ejoc.202000044
Ключевые слова Radicals; Nitroxides; Multi-spin systems; Cross-coupling; Synthesis design
Авторы Votkina Darya E. 1 , Petunin Pavel V. 1,2 , Zhivetyeva Svetlana I. 3 , Bagryanskaya Irina Yu. 3,4 , Uvarov Mikhail N. 4,5 , Kazantsev Maxim S. 3 , Trusova Marina E. 1 , Tretyakov Evgeny V. 3,4 , Postnikov Pavel S. 1
Организации
1 (Данные Web of science) Tomsk Polytech Univ, Res Sch Chem & Appl Biomed Sci, 30 Lenin Ave, Tomsk 634050, Russia
2 (Данные Web of science) Siberian State Med Univ, 2 Moskovskiy Trakt, Tomsk 634050, Russia
3 (Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Inst Organ Chem, 9 Ac Lavrentiev Ave, Novosibirsk 630090, Russia
4 (Данные Web of science) Novosibirsk State Univ, 2 Pirogova Str, Novosibirsk 630090, Russia
5 (Данные Web of science) RAS, VV Voevodsky Inst Chem Kinet & Combust, SB, 3 Inst Skaya Str, Novosibirsk 630090, Russia

Реферат: Iodine- and ethynyl-containing 'Kuhn'-verdazyls, oxoverdazyls, and nitronyl nitroxides were investigated as building blocks for the preparation of multi-spin systems via the Sonogashira reaction, and, as a result, eleven diradicals were prepared with fair yields. The reactivity of the building blocks indicates that oxoverdazyl iodides are effective starting components for the synthesis of diradicals via the Sonogashira coupling. The described one-step protocol allows combining different spin units, thereby facilitating the design of tolane-bridged diradicals and screening of their properties. The novel compounds were characterized by cyclic voltammetry, UV/Vis and electron spin resonance (ESR) spectroscopy. Although the electrochemical investigation and electronic spectra showed a negligible influence of radical moieties on each other, ESR data revealed a strong exchange interaction between two unpaired electrons. The prepared verdazyl-nitronylnitroxide diradicals have high stability at storage and hold promise for further investigation and application.
Библиографическая ссылка: Votkina D.E. , Petunin P.V. , Zhivetyeva S.I. , Bagryanskaya I.Y. , Uvarov M.N. , Kazantsev M.S. , Trusova M.E. , Tretyakov E.V. , Postnikov P.S.
Preparation of Multi-Spin Systems: A Case Study of Tolane-Bridged Verdazyl-Based Hetero-Diradicals
European Journal of Organic Chemistry. 2020. V.2020. N13. P.1996-2004. DOI: 10.1002/ejoc.202000044 WOS Scopus РИНЦ
Даты:
Опубликована online: 25 мар. 2020 г.
Опубликована в печати: 7 апр. 2020 г.
Идентификаторы:
Web of science WOS:000521454800001
Scopus 2-s2.0-85083377338
РИНЦ 43275500
OpenAlex W3010077181
Альметрики: