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

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

Journal

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

Output data

Year: 2020, Volume: 2020, Number: 13, Pages: 1996-2004 Pages count : 9 DOI: 10.1002/ejoc.202000044

Tags

Radicals; Nitroxides; Multi-spin systems; Cross-coupling; Synthesis design

Authors

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

Affiliations

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

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.

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 OpenAlex

Published online:	Mar 25, 2020
Published print:	Apr 7, 2020

Web of science:	WOS:000521454800001
Scopus:	2-s2.0-85083377338
Elibrary:	43275500
OpenAlex:	W3010077181

DB	Citing
Web of science	12
Scopus	9
OpenAlex	17