Comparative study of azobenzene and stilbene bridged crown ether p-tert-butylcalix 4 arene

Rojanathanes, Rojrit, Pipoosananakaton, Bongkot, Tuntulani, Thawatchai, Bhanthumnavin, Worawan, Orton, James B., Cole, Simon J., Hursthouse, Michael B., Grossel, Martin C. and Sukwattanasinitt, Mongkol (2005) Comparative study of azobenzene and stilbene bridged crown ether p-tert-butylcalix 4 arene. Tetrahedron, 61 (5), 1317-1324. (doi:10.1016/j.tet.2004.11.020).

Abstract

Photo-switchable calixarenes consisting of a stilbene or azobenzene bridge, spanning the narrow rim as a switching unit, were synthesized through reductive coupling of o-, m- and p-bis-benzaldehyde and bis-nitrobenzene-substituted calix[4]arenes. Both cis- and trans-stilbenes were produced from the reductive coupling of the o- and m-bis-benzaldehyde with the cis isomer being predominant for both regioisomers, whilst the coupling of p-bis-benzaldehyde gave only cis product. On the other hand, the only isolable product obtained from the reductive coupling of bis-o- and bis-m-nitrobenzene was the corresponding trans-azobenzene and the coupling product from bis-p-nitrobenzene was not stable. Each of the synthesized compounds showed a photostationary state in their cis-trans isomerization. The complexation of alkali metal ions was observed for only the o-azobenzene derivative suggesting that the lone pair of N-atom in the azo bridge participates in this process.

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