Rational Design of Low Molecular Mass Organogelators: Toward a Library of FunctionalN-Acyl-1,ω-Amino Acid Derivatives

Abstract

N‐Acyl amino acids RCONH(CH2)nCOOR1 represent a new family of organogelators that can be obtained in a combinatorial approach from libraries of activated acids and amino acids. The amounts required for gel formation (see picture) in solvents such as DMF are less than 1 mg mL−1 and the gels formed are very stable. n=5, 7, 10, 12; R=aromatic or aliphatic group; R1=H or alkali metal (Na).

Towards a universal organogelator: A general mixing approach to fabricate various organic compounds into organogels

“…Many of the metal complexes such as fatty acids salts [43], metal porphyrins [44] and metal phthalocyanins [45] have been known to be gelators. The metal complexes of many organic ligands like gluconamides [46], some molecules with nitrogen heterocyclic rings [47,48] and derivatives of phosphinic acid [34] can also be used as gelators.…”

Salts of 4-Substituted Dipicolinic Acid Derivatives − Very Low Molecular Mass Gelators of Aqueous DMSO

“…The most reliable approach so far is based on the covalent grafting of long aliphatic side-chain substituents to functional motifs prone to propagate one-directional Hbond interactions. [8] Elongated molecules containing urea [9] or amide groups [10] are among the archetypal examples of gelators obtained in this way. Long-chain moieties are believed to fine-tune solvophobic interactions and to frustrate three-dimensional crystal growth.…”

Rapid self-healing and anion selectivity in metallosupramolecular gels assisted by fluorine–fluorine interactions

“…Non-covalent interactions such as hydrogen bonding, p-p stacking, charge transfer interactions, and hydrophobic effects have been extensively utilized towards rational design of low molecular mass organo-and hydrogelators with new functional properties. [17][18][19][20] Peptides, 21 carbohydrates, 22 steroids, 23 ureaderivatives, 24 and simple fatty acids, 25 have been shown to exhibit remarkable ability to self-assemble into highly entangled fibrillar networks thereby able to encapsulate and immobilize solvent molecules. While a majority of the gelators have been discovered serendipitously, 26,27 continuing efforts have been made towards rational design of gelators with tunable properties as for example thermotropic polymorphism 28 or stimuli-responsiveness 29 including anion dependent gels 30 with interesting applications in molecular sensing.…”