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 Fedorova^b@

^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: fedorova@ineos.ac.ru

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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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

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