Supramolecular Gel Based on Crown-Ether-Appended Dynamic Covalent Macrocycles

Macromol Rapid Commun. 2019 Sep;40(17):e1800731. doi: 10.1002/marc.201800731. Epub 2019 Jan 23.

Abstract

A new type of dynamic covalent macrocycle with self-promoted supramolecular gelation behavior is developed. Under oxidative conditions, the dithiol compound containing a diamide alkyl linker with an odd number (7) of carbon chain and an appended crown ether shows a remarkable gelation ability in acetonitrile, without any template molecules. Due to the existence of crown ethers and disulfide bonds, the obtained gel shows a multiple stimuli-responsiveness behavior. The mechanical properties and reversibility of the gel are investigated. Computational modeling suggests that the peripheral chain for diamide hydrogen bonding is responsible for the gelation process.

Keywords: crown compounds; dynamic covalent macrocycles; gels; self-assembly; stimuli-responsiveness.

MeSH terms

  • Biocompatible Materials / chemistry*
  • Colloids / chemistry*
  • Computer Simulation
  • Crown Ethers / chemistry*
  • Gels / chemistry*
  • Hydrogen Bonding
  • Macrocyclic Compounds / chemistry*
  • Molecular Structure

Substances

  • Biocompatible Materials
  • Colloids
  • Crown Ethers
  • Gels
  • Macrocyclic Compounds