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Solution structure and equilibrium of new calix[4]resorcinarene complexes—prototype of molecular machines. NMR data
Authors:S V Kharlamov  A Y Ziganshina  A V Aganov  A I Konovalov  Sh K Latypov
Institution:(1) Institute of Organic and Physical Chemistry, Kazan Scientific Centre, Russian Academy of Sciences, Arbuzov St., 8, Kazan, 420088, Russia;(2) Kazan State University, Kremlevskaya St., 18, Kazan, 420008, Russia
Abstract:Association properties and molecular machine application of water soluble calix4]resorcinarene (1) with two aromatic guests (2-naphthol (2) and 1,5-naphthalenediamine (3)) have been investigated by various NMR methods (chemical shift, nOe and diffusion measurements) in aqueous solution at different concentrations and pH range. In neutral solution 1 strongly associates with 2, while only moderately associating with 3. Increase in concentration causes an increase in the stability of 1 + 3 and 1 + 2 + 3 complexes and produces high order complexes. The decrease of pH does not have an influence on 1 + 2 association, but disrupts 1 + 3 assembly. 1 can be used for the separation of 2 + 3 mixture in aqueous solution at moderate concentrations. The pH dependency of the association properties of the 1 + 3 system makes these compounds prime candidates for pH-responsive molecular machines applications.
Keywords:NMR  DOSY  Molecular machine  Host–  guest complex
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