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Reference type: Journal
Authors: Zimmerman SC, Zharov I, Wendland MS, Rakow NA, Suslick KS
Article Title: Molecular imprinting inside dendrimers.
Publication date: 2003
Journal: Journal of the American Chemical Society
Volume: 125
Issue: (44)
Page numbers: 13504-13518.
DOI: 10.1021/ja0357240
Alternative URL: http://www.chem.utah.edu/faculty/zharov/group/publications/JACS2003.pdf

Abstract: Synthetic hosts capable of binding porphyrins have been produced by a mixed-covalent-noncovalent imprinting process wherein a single binding site is created within cross-linked dendrimers. Two synthetic hosts were prepared, using as templates 5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrin and 5,10,15,20-tetrakis(3,5-dihydroxyphenyl)porphyrin. These two templates were esterified with, respectively, fourth- and third-generation Frechet-type dendrons containing homoallyl end-groups. The resulting tetra-and octadendron macromolecules underwent the ring-closing metathesis reaction using Grubbs' Type I catalyst, RUCl2(P(C6H5)(3))(2)(CHCH2C6H5), to give extensive interdendron cross-linking. Hydrolytic removal of the porphyrin cores afforded imprinted hosts whose ability to bind porphyrins with various peripheral substituents was investigated by UV-visible spectrophotometric titrations and size exclusion chromatography. The results indicate a high yield of imprinted sites that show high selectivity for binding of porphyrins capable of making at least four hydrogen bonds, but only a moderate degree of shape selectivity


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