Molecular Imprinting Inside Dendrimers

Steven C. Zimmerman, Ilya Zharov, Michael S. Wendland, Neal A. Rakow, Kenneth S Suslick

Research output: Contribution to journalArticlepeer-review


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 Fréchet-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.

Original languageEnglish (US)
Pages (from-to)13504-13518
Number of pages15
JournalJournal of the American Chemical Society
Issue number44
StatePublished - Nov 5 2003

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry


Dive into the research topics of 'Molecular Imprinting Inside Dendrimers'. Together they form a unique fingerprint.

Cite this