Synthesis and Binding Properties of Monohydroxy-cucurbit[7]uril: A Key Derivative for the Functionalization of Cu-curbituril Hosts

Nan Dong, Jing He, Tao Li, Andrea Peralta, Mehdi Rashvand Avei, Mingfang Ma, Angel Kaifer

Research output: Contribution to journalArticle

15 Scopus citations

Abstract

We present a simple, direct method to prepare monohydroxylated-cucurbit[7]uril (CB7-OH) through the direct oxidation of its precursor host, cucurbit[7]uril (CB7). Although the conversion takes place in low yield (14%), the isolation of CB7-OH from the reaction mixture is straightforward and the unreacted CB7 can be easily recovered. ITC measurements with several selected guests confirmed that CB7-OH binds all of them in aqueous solution with similar, albeit slightly lower, binding affinities than those observed with the unmodified CB7 host. ESI mass spectrometric competition experiments are consistent with the ITC measurements. A variety of spectroscopic and voltammetric measurements also verify that the CB7-OH complexes exhibit essentially identical properties to those of the CB7 com-plexes. DFT computational data also confirm the similar thermodynamic stabilities and structures of the CB7-OH and CB7 inclusion complexes. Finally, the high thermodynamic stability of the CB7-OH complexes was used to improve on the extraction efficiency of stir bar sorptive extraction methods after suitable modification of the active coating with CB7-OH.

Original languageEnglish (US)
JournalUnknown Journal
DOIs
StateAccepted/In press - Feb 8 2018

ASJC Scopus subject areas

  • Organic Chemistry

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