Issue 3, 2011
From the journal:

New Journal of Chemistry

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

Sergey P. Gromov,*a   Artem I. Vedernikov,a   Natalia A. Lobova,a   Lyudmila G. Kuz'mina,b   Stepan S. Basok,c   Yuri A. Strelenko,d   Michael V. Alfimova  and  Judith A. K. Howarde  

* Corresponding authors

a Photochemistry Centre, Russian Academy of Sciences, ul. Novatorov 7A-1, Moscow 119421, Russian Federation
E-mail: spgromov@mail.ru
Fax: +7 495 936 1255

b N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskiy prosp. 31, Moscow 119991, Russian Federation
E-mail: kuzmina@igic.ras.ru
Fax: +7 495 954 1279

c A. V. Bogatskiy Physicochemical Institute, National Academy of Sciences of Ukraine, Lustdorfskaya doroga 86, Odessa 65080, Ukraine

d N. D. Zelinskiy Institute of Organic Chemistry, Russian Academy of Sciences, Leninskiy prosp. 47, Moscow 119991, Russian Federation
E-mail: strel@ioc.ac.ru
Fax: +7 499 135 5328

e Chemistry Department, Durham University, South Road, Durham DH1 3LE, UK
E-mail: j.a.k.howard@durham.ac.uk
Fax: +44 0191 374 3745

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

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Article information

DOI
https://doi.org/10.1039/C0NJ00780C
Article type
Paper
Submitted
11 Oct 2010
Accepted
30 Nov 2010
First published
17 Jan 2011

New J. Chem., 2011,35, 724-737

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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

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