Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 125, Issue 44, Pages 13504-13518Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja0357240
Keywords
-
Categories
Funding
- NHLBI NIH HHS [HL 25934] Funding Source: Medline
- NIGMS NIH HHS [GM61067] Funding Source: Medline
Ask authors/readers for more resources
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available