A new versatile receptor platform.
We prepared a molecular receptor based on the molecular tweezer concept. Our system offers versatility, an extremely short synthetic route, good yield, large quantities, and finally having binding constants that equal the best known tweezer molecules when it comes to binding various nitroaromatics such as 1,3,5-trinitrotoluene (24 M(-1)), 1,3,5-trinitrobenzene (182 M(-1)), and 2,4,7-trinitrofluorenone (490 M(-1)) as determined using 1H NMR in CDCl3. It is notable that these binding constants are achieved although the molecular framework is not locked in a fixed and rigid conformation. The rigidity has been claimed to be the governing factor when it comes to achieving a large binding constant. We propose that our molecular tweezer system may be preorganized and that this explains the high binding constants observed. Further, we investigated the crystal structures of both the neutral receptor molecule and a complex with 1,3,5-trinitrobenzene and found that the molecule forms a pocket suited to accommodate flat aromatic analytes.
Krebs
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FC
The Danish Polymer Centre, RISØ National Laboratory, P.O. Box 49, DK-4000 Roskilde, Denmark. Frederik.krebs@risoe.dk
Jørgensen
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M
D018360:Crystallography, X-Ray; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D018716:Molecular Mimicry; D011956:Receptors, Cell Surface / Q000737:chemistry*; D011955:Receptors, Drug / Q000737:chemistry*
D011956:Receptors, Cell Surface; D011955:Receptors, Drug