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Catechol-Containing Schiff Bases on Thiacalixarene: Synthesis,Copper (II) Recognition,and Formation of Organic-Inorganic Copper-Based Materials
Authors:Pavel Padnya  Ksenia Shibaeva  Maxim Arsenyev  Svetlana Baryshnikova  Olga Terenteva  Igor Shiabiev  Artur Khannanov  Artur Boldyrev  Alexander Gerasimov  Denis Grishaev  Yurii Shtyrlin  Ivan Stoikov
Institution:1.A.M. Butlerov’ Chemistry Institute, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, Russia; (K.S.); (O.T.); (I.S.); (A.K.); (A.B.); (A.G.);2.G.A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 Tropinin Street, 603137 Nizhny Novgorod, Russia; (M.A.); (S.B.);3.Scientific and Educational Center of Pharmaceutics, Kazan Federal University, 420008 Kazan, Russia; (D.G.); (Y.S.)
Abstract:For the first time, a series of catechol-containing Schiff bases, tetrasubstituted at the lower rim thiacalix4]arene derivatives in three stereoisomeric forms, cone, partial cone, and 1,3-alternate, were synthesized. The structure of the obtained compounds was proved by modern physical methods, such as NMR, IR spectroscopy, and HRMS. Selective recognition (Kb difference by three orders of magnitude) of copper (II) cation in the series of d-metal cations (Cu2+, Ni2+, Co2+, Zn2+) was shown by UV-vis spectroscopy. Copper (II) ions are coordinated at the nitrogen atom of the imine group and the nearest oxygen atom of the catechol fragment in the thiacalixarene derivatives. High thermal stable organic-inorganic copper-based materials were obtained on the base of 1,3-alternate + Cu (II) complexes.
Keywords:thiacalix[4]arenes  Schiff base  synthesis  complexing properties  copper cation  organic-inorganic materials
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