Instantaneous low temperature gelation by a multicomponent organogelator liquid system based on ammonium salts

J Am Chem Soc. 2008 Jun 25;130(25):7967-73. doi: 10.1021/ja8002777. Epub 2008 Jun 3.

Abstract

A new synergistic multicomponent organogelator liquid system (MOGLS) was discovered during the standard protocol of tartaric acid-mediated racemic resolution of (+/-)- trans-1,2-diaminocyclohexane. The MOGLS is formed by a 0.126 M methanolic solution of (1 R,2 R)-(+)-1,2-diaminocyclohexane L-tartrate and 1 equiv of concentrated hydrochloric acid. Nonreversible gelation of oxygenated and nitrogenated solvents occurs efficiently at low temperature. Several features make this system unique: (1) it is a multicomponent solution where each of the five components is required for the organogelation property; (2) the multicomponent organogelator liquid system (MOGLS) is formed by simple, small, and commercially available chiral building blocks dissolved in a well-defined solvent system (MeOH/HCl/H2O); (3) the chiral building blocks are easily amenable for further modifications in structure-property relationship studies; (4) the gelation phenomenon takes place efficiently at low temperature upon warming up the isotropic solution, conversely to the typical gel preparation protocol (gel formation upon cooling down the isotropic solution); (5) the formed organic gels are not thermoreversible in spite of the noncovalent interactions that hold the 3D-fibrillar network together.

Publication types

  • Research Support, Non-U.S. Gov't
  • Retracted Publication

MeSH terms

  • Cyclohexylamines / chemistry*
  • Gels / chemistry*
  • Hydrochloric Acid / chemistry
  • Methanol / chemistry
  • Molecular Structure
  • Tartrates / chemistry*
  • Temperature

Substances

  • Cyclohexylamines
  • Gels
  • Tartrates
  • 1,2-cyclohexanediamine
  • Hydrochloric Acid
  • tartaric acid
  • Methanol