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ISSN 1998-9539

Thienyl-phenyl Ethylenes with Crown Ether Fragments and Their Photocyclization Products: UV-Vis, NMR, Redox Response for Complexation. A 18-Crown-6 Ether Restricted with a Tricyclic Aromatic Moiety

Anatoliy Botezatu,a Sergey Tokarev,b Yulia Sotnikova,a Anna Moiseeva,a Natalya Dyachenko,a Alexander Anisimov,a Yuri Fedorov,b Andrey Khoroshutin,a,c and Olga Fedorovab@
aDepartment of Chemistry, M.V. Lomonosov Moscow State University, 119991 Moscow, Russia
bA.N. Nesmeyanov Institute of Elementoorganic Compounds of Russian Academy of Sciences, 119334 Moscow, Russia
cAll-Russian Institute of Scientific and Technical Information of Russian Academy of Sciences (VINITI), 125190 Moscow, Russia
@Corresponding author E-mail:
DOI: 10.6060/mhc200496f
Macroheterocycles 2020 13(2) 163-171
The synthesis of new compounds possessing 18-crown-6 fragment is reported: 1-(2-thienyl)-2-(meta-benzo-18-crown-6)stilbene and 1-(3-thienyl)-2-(meta-benzo-18-crown-6)stilbenе, as well as two isomeric products of Mallory cyclization of 2-thienylstilbene, containing a tricyclic fragment annulated to the crown ether moiety. Binding constants of these compounds with Ca2+ and Ba2+ have been measured. Besides, dependence of the 1H NMR chemical shifts of both stilbenes and cyclization products on their binding to Ba2+ has been studied. Redox response on the complexation is also elucidated. Among the studied compounds, a sterically congested photocyclization product exhibits an unusual dependence of chemical shifts upon complexation, as well as redox behaviour.


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