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Cation binding by 21,31-diphenyl-l 2,42-dioxo-7,10,13-trioxa-1,4(3,1)-diquinoxalina-2 (2,3),3(3,2)-diindolizinacyclopentadecaphane and its acyclic analog

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Abstract

The binding of cations Li+, Na+, K+, Cs+, Ag+, Zn2+, Ni2+, Co2+, NH4 + (group I), H+, Mg2+, Al3+, Ga3+ (group II), and Ca2+, Pb2+ (group III) by 21,31-diphenyl-l 2,42-dioxo- 7,10,13-trioxa-l,4(3,1)-diquinoxalina-2(2,3),3(3,2)-diindolizinacyclopentadecaphane (1), which contains two indolizine and two quinoxaline fragments and 3,6,9-trioxaundecanes spacer, and by its acyclic analog (2) was studied using cyclic voltammetry in MeCN/0.1 M Bu4NBF4. It was concluded that the ions of group I are not bound by these compounds, the ions of group II exhibit the reversible redox-switched binding by the carbamoyl groups of the quinoxaline fragments, whereas the ions of group III are bound not only by the initial compounds and radical cations 1 and 2, but also by dication 1. This binding of the Ca2+ and Pb2+ ions stabilizes dication 1.

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    V. V. Yanilkin, N. V. Nastapova, A. S. Stepanov, A. A. Kalinin & V. A. Mamedov

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  1. V. V. Yanilkin
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  2. N. V. Nastapova
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  3. A. S. Stepanov
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  4. A. A. Kalinin
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Correspondence to V. V. Yanilkin.

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Dedicated to Academician A. I. Konovalov on his 75th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 89–94, January, 2009

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Yanilkin, V.V., Nastapova, N.V., Stepanov, A.S. et al. Cation binding by 21,31-diphenyl-l 2,42-dioxo-7,10,13-trioxa-1,4(3,1)-diquinoxalina-2 (2,3),3(3,2)-diindolizinacyclopentadecaphane and its acyclic analog. Russ Chem Bull 58, 89–94 (2009). https://doi.org/10.1007/s11172-009-0013-7

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