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

Бібліографічні деталі
Parent link:European Journal of Organic Chemistry
Vol. 2020, iss. 13.— 2020.— [P. 1996-2004]
Співавтор: Национальный исследовательский Томский политехнический университет Исследовательская школа химических и биомедицинских технологий (ИШХБМТ)
Інші автори: Votkina D. E. Darjya Evgenjevna, Petunin P. V. Pavel Vasilievich, Zhivetjeva S. I. Svetlana Ivanovna, Bagryanskaya I. Yu. Irina Yurjevna, Uvarov M. N. Mikhail Nikolaevich, Kazantsev M. S. Maksim Sergeevich, Trusova M. E. Marina Evgenievna, Tretjyakov E. V. Evgeny Viktorovich, Postnikov P. S. Pavel Sergeevich
Резюме:Title screen
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.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.
Мова:Англійська
Опубліковано: 2020
Предмети:
электронный ресурс
труды учёных ТПУ
radicals
nitroxides
multi-spin systems
cross-coupling
synthesis design
радикалы
мультиспиновые системы
перекрестные связи
Онлайн доступ:https://doi.org/10.1002/ejoc.202000044
Формат: Електронний ресурс Частина з книги
KOHA link:https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=663337

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