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Self-assembly involving alkanediammonium ions and stereospecific [2+2] photocycloaddition of (18-crown-6)stilbene

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Abstract

Complexation between (18-crown-6)stilbene and alkanediammonium ions +H3N(CH2)nNH +3 (n = 2−4) resulting in the pseudo-sandwich 2:1 stilbene—dication complexes and 1:1 stilbene—dication complexes was studied by NMR spectroscopy. The stability of the complexes decreases as the methylene chain length in the alkanediammonium ion increases. UV photolysis of the bis-ligand complexes produces two major products, viz., the rctt isomer of a biscrown-containing cyclobutane derivative formed as a result of intra-supramolecular [2+2] photocycloaddition and a crown-containing phenanthrene derivative (product of electrocyclization reaction). The effective quantum yields of both cyclization reactions occurring in the pseudo-sandwich complexes increase as the number of methylene units in the dication decreases.

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Authors and Affiliations

  1. Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, 1 prosp. Akad. Semenova, Chernogolovka, 142432, Moscow Region, Russian Federation

    T. P. Martyanov, A. P. Vorozhtsov, N. A. Slesarenko & E. N. Ushakov

  2. Photochemistry Center of the Russian Academy of Sciences, Federal Scientific Research Center “Crystallography and Photonics”, Russian Academy of Sciences, Build. 1, 7a ul. Novatorov, 119421, Moscow, Russian Federation

    T. P. Martyanov, A. P. Vorozhtsov, N. A. Aleksandrova, E. N. Ushakov & S. P. Gromov

  3. Chernogolovka Branch of the N. N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, 142432, Chernogolovka, Moscow Region, Russian Federation

    I. V. Sulimenkov

  4. Department of Chemistry, Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    S. P. Gromov

Authors
  1. T. P. Martyanov
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  2. A. P. Vorozhtsov
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  3. N. A. Aleksandrova
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  4. I. V. Sulimenkov
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  5. N. A. Slesarenko
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  6. E. N. Ushakov
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  7. S. P. Gromov
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Corresponding authors

Correspondence to T. P. Martyanov or S. P. Gromov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

This work was financially supported by the Russian Science Foundation (Project No. 22-13-00064, except 1H NMR titration and mass spectra). Mass spectrometric analysis and 1H NMR titration were financially supported by the Ministry of Science and Higher Education of the Russian Federation (State Assignments No. 122040500059-8 and AAAA-A19-119070790003-7, respectively).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 3, pp. 740–748, March, 2023.

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Martyanov, T.P., Vorozhtsov, A.P., Aleksandrova, N.A. et al. Self-assembly involving alkanediammonium ions and stereospecific [2+2] photocycloaddition of (18-crown-6)stilbene. Russ Chem Bull 72, 740–748 (2023). https://doi.org/10.1007/s11172-023-3838-2

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  • DOI: https://doi.org/10.1007/s11172-023-3838-2

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