Integrating chemosensors for amine-containing compounds into cross-linked dendritic hosts

Eric Mertz, Stephanie L. Elmer, Amy M. Balija, Steven C. Zimmerman

Research output: Contribution to journalArticlepeer-review


Trifluoroacetylazo dye 1, a known chemosensor for amines, has been integrated into cross-linked dendrimer hosts. Thus, boronic acid 16 was linked to iododye 9 via a Suzuki coupling reaction. In situ deprotection and alkylation with dendrons 3 and 4, containing 8 homoallyl or allyl ether groups, respectively, afforded dendrons 18 and 19 with chemosensor units at their focal point. Conversion of 18 (19) to the bis-imine of butane 1,4-diamine, extensive cross-linking via the ring closing metathesis reaction with Grubbs catalyst 25, and hydrolysis produced dendrimer hosts 28 and 29. Host-guest studies with a small library of amines and alcohols showed 28 and 29 to selectively signal certain diamines but not due to template mediated imprinting. Graphical Abstract.

Original languageEnglish (US)
Pages (from-to)11191-11204
Number of pages14
Issue number49
StatePublished - Nov 29 2004


  • Chemosensor
  • Dendritic host
  • Diamines

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery


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