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Новосибирский институт органической химии им. Н.Н. Ворожцова
Сибирского отделения Российской академии наук



В журнале European Journal of Organic Chemistry   (IF 3.029) опубликована статья  с участием сотрудников Института: к.х.н. С.И. Живетьевой (нс ЛИНИРР), д.х.н. И.Ю. Багрянской (внс, руководитель группы ГРСА), к.х.н. М.С. Казанцева (снс, ЛОЭ) и д.х.н. Е.В. Третьякова (зам. директора по науке, зав.лаб ЛИНИРР)

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

Darya E. Votkina, Pavel V. Petunin, Svetlana I. Zhivetyeva, Irina Yu. Bagryanskaya, Mikhail N. Uvarov, Maxim S. Kazantsev,  Marina E. Trusova,  Evgeny V. Tretyakov,  Pavel S. Postnikov

European Journal of Organic Chemistry, Volume 2020, Issue13, April 7, 2020 Pages 1996-2004

First published:04 March 2020

DOI:https://doi.org/10.1002/ejoc.202000044

Hot Topic: C-C Coupling

Abstract

Sonogashira coupling was investigated as a promising strategy for the synthesis of a multi‐spin system based on ‘Kuhn'‐verdazyls, oxoverdazyls, and nitronyl‐nitroxides. Eleven hetero‐diradicals were isolated in up to 56 % yields by a one‐step protocol. Oxoverdazyl radicals had the highest reactivity. This research opens access to simple design and investigation of conjugated diradicals.

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Abstract

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.

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