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PCage: Fluorescent Molecular Temples for Binding Sugars in Water.

Wenqi Liu1, Yu Tan2, Leighton O Jones1

  • 1Department of Chemistry, 2145 Sheridan Road, Northwestern University, Evanston, Illinois 60208, United States.

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Area of Science:

  • Supramolecular Chemistry
  • Carbohydrate Chemistry
  • Chemical Sensing

Background:

  • Recognizing carbohydrates in water is difficult due to their complex structures and hydrophilicity.
  • Synthetic receptors require high selectivity and specificity for effective carbohydrate detection.

Purpose of the Study:

  • To design and synthesize novel pyrene-based, temple-shaped receptors for carbohydrate recognition in aqueous environments.
  • To investigate the binding mechanisms and selectivity of these receptors for common sugars.

Main Methods:

  • Synthesis of pyrene-based, temple-shaped molecular receptors.
  • Utilizing [C-H···π] interactions between pyrene panels and carbohydrate substrates.
  • Employing [C-H···O] hydrogen bonds between pyridinium groups and sugar hydroxyls.
  • Investigating binding selectivity using various common sugars.

Main Results:

  • The synthesized temple receptors effectively recognize a range of common sugars in water.
  • High selectivity was observed for glucose and its derivatives.
  • Enhanced fluorescence was detected upon glucose binding, indicating potential for sensing applications.

Conclusions:

  • Pyrene-based temple receptors offer a promising strategy for selective carbohydrate recognition in water.
  • The observed fluorescence enhancement provides a basis for developing fluorescent glucose sensors.
  • This work advances the field of synthetic receptors for biologically relevant molecules.