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Molecular recognition using tetralactam macrocycles with parallel aromatic sidewalls.

Dong-Hao Li1, Bradley D Smith1

  • 1Department of Chemistry and Biochemistry, University of Notre Dame, 236 Nieuwland Science Hall, Notre Dame, Indiana 46556, United States.

Beilstein Journal of Organic Chemistry
|June 6, 2019
PubMed
Summary
This summary is machine-generated.

Tetralactam macrocycles with parallel aromatic sidewalls and internal NH groups act as versatile hosts. Their amphiphilic cavities and conformational flexibility enable binding of diverse guests in water and organic solvents.

Keywords:
fluorescent dyehost–guest chemistryhydrogen bondinghydrophobic effectmacrocyclesrotaxanesupramolecular

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Tetralactam macrocycles possess parallel aromatic sidewalls and four internal NH residues.
  • These macrocycles feature amphiphilic binding pockets, mimicking protein active sites.

Purpose of the Study:

  • To review the supramolecular properties of tetralactam macrocycles.
  • To highlight their versatility as hosts for various guest molecules.

Main Methods:

  • Review of existing literature on tetralactam macrocycles.
  • Analysis of binding properties in aqueous and organic media.

Main Results:

  • Macrocycles exhibit high affinity for diverse guests due to hydrophobic effects and NH interactions, which vary with solvent polarity.
  • Amphiphilic cavity and conformational flexibility contribute to host-guest complexation.
  • Effective binding of organic biscarbonyl derivatives, dyes, acenes, metal complexes, and saccharides was observed.

Conclusions:

  • Tetralactam macrocycles are highly adaptable hosts for supramolecular applications.
  • Their unique cavity properties allow for selective guest binding in different solvent environments.
  • These macrocycles show significant potential in various chemical and biological applications.