125379-27-3Relevant articles and documents
Dynamic factors in the design of redox-switched calix[4]arene cationophores
Bethell, Donald,Dougherty, Gary,Cupertino, Domenico C.
, p. 407 - 416 (2007/10/03)
Syntheses are described of four calix[4]arenes, each bearing a 9,10-anthraquinone moiety as a redox switch to modify cation binding. The first compound, having a triester-amide lariat-type structure, showed no experimental evidence (from cyclic voltammetry in acetonitrile solution) for enhancement of binding of alkalimetal cations, indicating negligible interaction between the binding site and the switchable group. Computer modelling showed that a large steric barrier prevents rotation of the switch into the energetically favourable position that would enhance cation binding. Compounds in which the anthraquinone formed part of a 1,3-bridging unit spanning the lower rim of the calix showed large cation-binding enhancements, the values being affected by the other, auxiliary groups on the lower rim of the calixarene. Unusual CV behaviour was observed in the case of the compound with two methoxy auxiliary donor groups in the presence of K+ , but not with Na+ . Computer modelling and NMR spectroscopic evidence indicates that this effect is attributable to a slow change of the calixarene from a cone to a partial cone conformation in binding K+, whereas the smaller Na+ fits easily into the available cavity of the cone conformation. Acta Chemica Scandinavica 1998.
Polymeric calixarenes. Synthesis, polymerisation and Na+ complexation of a calix[4]arene methacrylate
Harris,Barrett,McKervay
, p. 1224 - 1225 (2007/10/02)
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Selective Monohydrolysis of a Calixarene Tetraethyl Ester with Trifluoroacetic Acid and its Inhibition by Na+ Ion: Evidence for Hydronium Ion Complexation
Boehmer, Volker,Vogt, Walter,Harris, Stephen J.,Leonard, Raymond, G.,Collins, Elizabeth M.,et al.
, p. 431 - 432 (2007/10/02)
Calixarene tetraethyl ester (1a) is hydrolysed by trifluoroacetic acid with the loss of one, and only one, ester group to form a monoacid triester; the process, which is inhibited by Na+ ion, is believed to involve specific hydronium ion complexation within the calixarene receptor.