Pillar[5]arenes Bearing Amide and Carboxylic Groups as Synthetic Receptors for Alkali Metal Ions

Luidmila S. Yakimova, Dmitry N. Shurpik, Aigul R. Makhmutova, and Ivan I. Stoikov^@

Kazan Federal University, A.M. Butlerov Chemical Institute, 420008 Kazan, Russian Federation

^@Corresponding author E-mail: ivan.stoikov@mail.ru

DOI: 10.6060/mhc170511s

Macroheterocycles2017 10(2) 226-232

Pillar[5]arenes bearing amide and carboxylic groups have demonstrated recognition performance for some representative alkali metal ions including Li⁺, Na⁺, K⁺ and Cs⁺ in series cations of s- and d-metals compared to pillar[5]arenes with hydroxyl, methoxy and acetone fragments. Their complexation abilities toward these cations were evaluated by UV–Vis technique. The complexation results revealed that pillar[5]arene, containing glicylglicyne groups, were the most efficient cation receptors for Li⁺, Na⁺, K⁺ and Cs⁺ over other synthesized and studied pillar[5]arenes. Introduction of long glycylglycide fragments into macrocycle structure allowed to increase the association constant logarithm in the case of Li⁺ by 2 orders. In addition, in the set of macrocycles, incorporation of the additional amide fragments and carboxyl group into macrocycle structure leads to increasing the binding efficiency with alkali metal cations.

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Pillar[5]arenes Bearing Amide and Carboxylic Groups as Synthetic Receptors for Alkali Metal Ions

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