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Quantitative SERS Detection of Uric Acid via Formation of Precise Plasmonic Nanojunctions within Aggregates of Gold Nanoparticles and Cucurbit[n]uril
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Acyclic cucurbit[n]uril congeners are high affinity hosts.

Da Ma1, Peter Y Zavalij, Lyle Isaacs

  • 1Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.

The Journal of Organic Chemistry
|June 15, 2010
PubMed
Summary
This summary is machine-generated.

New acyclic cucurbit[n]uril congeners effectively host ammonium ions in water. These flexible molecules exhibit high binding affinities, demonstrating potential as versatile receptors in aqueous solutions.

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Area of Science:

  • Supramolecular Chemistry
  • Host-Guest Chemistry
  • Organic Synthesis

Background:

  • Cucurbit[n]urils are a well-established class of macrocyclic hosts known for their strong binding of ammonium ions.
  • The development of acyclic analogs offers potential for modified host properties and applications.
  • Understanding the structural basis of host-guest interactions is crucial for designing selective molecular receptors.

Purpose of the Study:

  • To design and synthesize novel acyclic cucurbit[n]uril congeners.
  • To investigate their host properties for ammonium ions in aqueous media.
  • To elucidate the structural features governing their binding affinity and selectivity.

Main Methods:

  • Synthesis of acyclic cucurbit[n]uril congeners using methylene bridged glycoluril tetramer building blocks.
  • X-ray crystallography to characterize the structure of the free hosts and their complexes with diamine guests.
  • Binding affinity measurements (Ka) in buffered aqueous solutions under varying metal cation concentrations.

Main Results:

  • Acyclic cucurbit[n]uril congeners with flexible methylene bridged backbones were successfully synthesized and characterized.
  • These hosts bind a variety of ammonium ions in water with high affinities (Ka from ~10^5 M^-1 to >10^9 M^-1).
  • Binding affinity is reduced by metal cations due to competitive binding, and selectivity is lower than rigid cucurbit[n]urils due to backbone flexibility.

Conclusions:

  • Acyclic cucurbit[n]uril receptors containing four or more glycoluril units retain significant ammonium ion binding capabilities.
  • The flexible methylene bridged backbone allows adaptation to guest structures, influencing binding affinity and selectivity.
  • Aromatic walls bearing substituents are crucial for high-affinity recognition, highlighting the importance of specific structural motifs.