Y. Tong et al., Sn(IV) porphyrins as NMR shift reagents and supramolecular protecting groups: Preparation of a carboxylate-catenane porphyrin complex, ORG LETT, 1(9), 1999, pp. 1343-1346
Coordination of a carboxylic acid diaryl crown ether to a Sn(IV) porphyrin
promotes its ability to act as a template for the formation of a [2]catenan
e: in the absence of the porphyrin the acid-crown yields only a tiny amount
of the interlocked derivative, Once isolated the free acid-[2]catenane pre
sents extremely broad resonances in its 500 MHz H-1 NMR spectrum, but compl
exation to a Sn(IV) porphyrin results in dramatic resolution via a combinat
ion of dynamic and dispersive effects.