Development of a microfluidic "click chip" incorporating an immobilized Cu(i) catalyst

Hairong Li, Joseph J. Whittenberg, Haiying Zhou, David Ranganathan, Amit V. Desai, Jan Koziol, Dexing Zeng, Paul J.A. Kenis, David E. Reichert

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

We have developed a microfluidic "click chip" incorporating an immobilized Cu(i) catalyst for click reactions. The microfluidic device was fabricated from polydimethylsiloxane (PDMS) bonded to glass and featured ∼14400 posts on the surface to improve catalyst immobilization. This design increased the immobilization efficiency and reduces the reagents' diffusion time to an active catalyst site. The device also incorporates five reservoirs to increase the reaction volume with minimal hydrodynamic pressure drop across the device. A novel water-soluble Tris-(benzyltriazolylmethyl)amine (TBTA) derivative capable of stabilizing Cu(i), ligand 2, was synthesized and successfully immobilized on the chip surface. The catalyst immobilized chip surface was characterized by X-ray photoelectron spectroscopy (XPS). The immobilization efficiency was evaluated via radiotracer methods: the immobilized Cu(i) was measured as 1136 ± 272 nmol and the surface immobilized Cu(i) density was 81 ± 20 nmol cm-2. The active Cu(i)-ligand 2 could be regenerated up to five times without losing any catalyst efficiency. The "click" reaction of Flu568-azide and propargylamine was studied on chip for proof-of-principle. The on-chip reaction yields were ca. 82% with a 50 min reaction time or ca. 55% with a 15 min period at 37 °C, which was higher than those obtained in the conventional reaction. The on-chip "click" reaction involving a biomolecule, cyclo(RGDfK) peptide was also studied and demonstrated a conversion yield of ca. 98%. These encouraging results show promise on the application of the Cu(i) catalyst immobilized "click chip" for the development of biomolecule based imaging agents. This journal is

Original languageEnglish (US)
Pages (from-to)6142-6150
Number of pages9
JournalRSC Advances
Volume5
Issue number8
DOIs
StatePublished - 2015

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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    Li, H., Whittenberg, J. J., Zhou, H., Ranganathan, D., Desai, A. V., Koziol, J., Zeng, D., Kenis, P. J. A., & Reichert, D. E. (2015). Development of a microfluidic "click chip" incorporating an immobilized Cu(i) catalyst. RSC Advances, 5(8), 6142-6150. https://doi.org/10.1039/c4ra15507f