Beilstein J. Org. Chem.2010,6, No. 10, doi:10.3762/bjoc.6.10
bulky esters were not recognized by this hemicarcerand. This size selective molecular recognition could be controlled by a negative cooperative allosteric effect: coordination of a triscarbonyl rhenium chloride fragment to the bipyridine causes a conformational rearrangement that orientates the
resorcinarene moieties in different directions so that they cannot act cooperatively in the binding of the substrate.
Keywords: allosteric receptors; 2,2′-bipyridine; hemicarcerand; molecular recognition; resorcin[4]arene; Introduction
Nature uses allosteric effects in a very elegant manner to control
derivatives of this first example of an allosteric hemicarcerand and their metal complexes formed upon coordination to metal salts or complexes like AgBF4, CuBF4, [Cuphen]BF4, or [(CO)5ReCl] [28]. Among these, bis(resorcin[4]arene) substituted 2,2′-bipyridine 2 is a structural isomer of 1 differing only in
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Graphical Abstract
Scheme 1:
Bis(resorcinarene) esters of 4,4′- and 4,6′-(2,2′-bipyridyl)dicarboxylic acid, 1 and 2, respectivel...