Jump to main content
Jump to site search

Issue 3, 2011
Previous Article Next Article

Controlled self-assembly of bis(crown)stilbenes into unusual bis-sandwich complexes: structure and stereoselective [2+2] photocycloaddition

Author affiliations

Abstract

It was shown by 1H NMR spectroscopy that symmetrical bis(crown)stilbenes (L) and small alkali and alkaline-earth metal cations form 1(L) ∶ 1(Mm+) and 1(L) ∶ 2(Mm+) complexes in MeCN solutions. In the case of large or hydrated metal cations such as Cs+, Rb+, K+, Ba2+, Sr2+, [Ca(H2O)x]2+ and stilbenes with a small crown-ether cavity as compared with the metal cation size, stable bis-sandwich complexes 2(L) ∶ 2(Mm+) can also be formed. A stable bis-pseudosandwich 2 ∶ 2 complex is also produced from bis(18-crown-6)stilbene with the propanediammonium ion. The effect of the crown-ether size and the cation size and nature on the route of stilbene phototransformation and product composition was elucidated. The bis-(pseudo)sandwich complexes undergo effective stereoselective [2+2] photocycloaddition giving mainly rctt isomers of new 1,2,3,4-tetracrown cyclobutanes. The structures of complexes of bis(crown)stilbenes and obtained cyclobutanes were confirmed by X-ray diffraction.

Graphical abstract: Controlled self-assembly of bis(crown)stilbenes into unusual bis-sandwich complexes: structure and stereoselective [2+2] photocycloaddition

Back to tab navigation

Supplementary files

Publication details

The article was received on 11 Oct 2010, accepted on 30 Nov 2010 and first published on 17 Jan 2011


Article type: Paper
DOI: 10.1039/C0NJ00780C
Citation: New J. Chem., 2011,35, 724-737
  •   Request permissions

    Controlled self-assembly of bis(crown)stilbenes into unusual bis-sandwich complexes: structure and stereoselective [2+2] photocycloaddition

    S. P. Gromov, A. I. Vedernikov, N. A. Lobova, L. G. Kuz'mina, S. S. Basok, Y. A. Strelenko, M. V. Alfimov and J. A. K. Howard, New J. Chem., 2011, 35, 724
    DOI: 10.1039/C0NJ00780C

Search articles by author

Spotlight

Advertisements