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Synthesis, structure, and electrochemical properties of 12,42-dioxo-21,31-diphenyl-7,10,13-trioxa-1,4(3,1)-diquinoxalina-2(2,3),3(3,2)-diindolizinacyclopentadecaphane

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Abstract

The oxidative dehydrocyclization of the 3-(indolizin-2′-yl)-2-oxoquinoxaline monopodand performed either electrochemically or under the action of molecular iodine affords new redox-active heterocyclophane consisting of the redox-switchable biindolizine fragment combined with the polyether-bridged π-deficient quinoxaline systems. The single-crystal X-ray diffraction study showed that the trioxaundecane chain of heterocyclophane adopts an extended conformation, and one of the phenyl substituents of the molecule closes the pseudocavity formed by the spacer from one of the sides. The cyclic voltammetric study of heterocyclophane in MeCN and DMF showed the three-step oxidation of the indolizine fragments accompanied by the single-electron transfer in each step. The first and third steps are reversible, and the second step is irreversible. The oxidation at potentials of the first peak gives rise to stable radical cations detected by the ESR method (g = 2.0024, a 2N = 0.26 mT).

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Authors and Affiliations

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

    V. A. Mamedov, A. A. Kalinin, V. V. Yanilkin, N. V. Nastapova, V. I. Morozov, A. A. Balandina, A. T. Gubaidullin, O. G. Isaikina, A. V. Chernova, Sh. K. Latypov & I. A. Litvinov

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

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Dedicated to Professor E. A. Berdnikov on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1991–2003, October, 2007.

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Mamedov, V.A., Kalinin, A.A., Yanilkin, V.V. et al. Synthesis, structure, and electrochemical properties of 12,42-dioxo-21,31-diphenyl-7,10,13-trioxa-1,4(3,1)-diquinoxalina-2(2,3),3(3,2)-diindolizinacyclopentadecaphane. Russ Chem Bull 56, 2060–2073 (2007). https://doi.org/10.1007/s11172-007-0322-7

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  • DOI: https://doi.org/10.1007/s11172-007-0322-7

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