Instantaneous Low Temperature Gelation by a Multicomponent Organogelator Liquid System Based on Ammonium Salts

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.

Anion-tuning of supramolecular gel properties

“…25,42, [149][150][151][152][153][154][155][156][157][158][159][160][161][162][163][164][165][166][167][168] As well as being a pH tunable LMWG the ability of 3.10 to gelate water in this pH range allows for the study of the influence of the anion species on gelation ability of this compound in water. Table 3.2 shows the results of the systematic study of the gelation ability of 3.10 in acidified water using different inorganic acids to provide the anion variation.…”

“…25,42, [149][150][151][152][153][154][155][156][157][158][159][160][161][162][163][164][165][166][167][168] Rheological characterisation, in conjunction with TEM and SEM imaging, of the H 2 SO 4 acidified gels indicated a cellular solid gel material that consists of load bearing struts interconnected via crosslinks or junction points which deform by bending. 173,180,182,183 The anion tuning of the gel characteristics was accomplished by changing the identity of the anion by changing the acid used to adjust the pH of the water solutions.…”

Encapsulation of Dye Molecules and Nanoparticles in Hollow Organogel Fibers of a Nonchiral Polyurethane Model Compound

“…There is a recent report on the fabrication of a low-molecular-mass organogel system through synergistic multi-component interactions, in which the presence of five components is required to form a gel. [22] Threedimensional fibrillar network of the gels can be comprised of different types of structures, for example, solid [17] or hollow fibers, [18,23] strands, and tapes, [3] depending on the type of noncovalent interaction and the molecular geometry of the organogelators.…”

Water-in-oil gel emulsions from a cholesterol derivative: Structure and unusual properties

“…Programmed self-assembly of low-molecular-mass compounds in water and organic solvents to form physical gels with desired properties have gained considerable attention during the last few decades [1][2][3][4][5][6][7][8]. This is because, on one hand, it can offer unique features to create various superstructures with respect to self-assembly phenomena [9][10][11][12][13][14], and, on the other hand, it has potentials for creating new soft materials, which may find uses in oil recovery, controlled release, bioactivity maintenance, separation of proteins, regenerative medicine, tissue engineering and template preparation of micro-nano-materials etc.…”