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

Article abstract of DOI:10.1021/ja8002777

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 (1R,2R)-(+)-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.