Research output: Contribution to journal › Article › peer-review
Preparation of Multi-Spin Systems : A Case Study of Tolane-Bridged Verdazyl-Based Hetero-Diradicals. / Votkina, Darya E.; Petunin, Pavel V.; Zhivetyeva, Svetlana I. et al.
In: European Journal of Organic Chemistry, Vol. 2020, No. 13, 07.04.2020, p. 1996-2004.Research output: Contribution to journal › Article › peer-review
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TY - JOUR
T1 - Preparation of Multi-Spin Systems
T2 - A Case Study of Tolane-Bridged Verdazyl-Based Hetero-Diradicals
AU - Votkina, Darya E.
AU - Petunin, Pavel V.
AU - Zhivetyeva, Svetlana I.
AU - Bagryanskaya, Irina Yu
AU - Uvarov, Mikhail N.
AU - Kazantsev, Maxim S.
AU - Trusova, Marina E.
AU - Tretyakov, Evgeny V.
AU - Postnikov, Pavel S.
N1 - Publisher Copyright: © 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2020/4/7
Y1 - 2020/4/7
N2 - 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.
AB - 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.
KW - Cross-coupling
KW - Multi-spin systems
KW - Nitroxides
KW - Radicals
KW - Synthesis design
UR - http://www.scopus.com/inward/record.url?scp=85083377338&partnerID=8YFLogxK
U2 - 10.1002/ejoc.202000044
DO - 10.1002/ejoc.202000044
M3 - Article
AN - SCOPUS:85083377338
VL - 2020
SP - 1996
EP - 2004
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 13
ER -
ID: 24027534