Synthesis and supramolecular self-assembly of glutamic acid-based squaramides

We describe the preparation and characterization of two new unsymmetrical squaramide-based organogelators. The synthesis of the compounds was carried out by subsequent amine condensations starting from dimethyl squarate. The design of the gelators involved a squaramide core connected on one side to...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2018-08, Vol.14 (1), p.2065-2073
Main Authors: Alegre-Requena, Juan V, Häring, Marleen, Sonsona, Isaac G, Abramov, Alex, Marqués-López, Eugenia, Herrera, Raquel P, Díaz Díaz, David
Format: Article
Language:English
Subjects:
Acids
Catalysis
Chemistry
Cooling
Electron microscopy
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Gelation
Gels
Glutamic acid
glutamic acid derivative
Infrared spectroscopy
organogel
Phase transitions
Rheology
Self-assembly
squaramide
supramolecular gel
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Summary:We describe the preparation and characterization of two new unsymmetrical squaramide-based organogelators. The synthesis of the compounds was carried out by subsequent amine condensations starting from dimethyl squarate. The design of the gelators involved a squaramide core connected on one side to a long aliphatic chain and on the other side to a glutamic acid residue. The gelator bearing the free carboxylic groups showed a lower gelation capacity than its precursor diester derivative. Some selected gels were further studied by infrared spectroscopy, rheology and electron microscopy. Critical gelation concentrations and gel-to-sol transition temperatures were also determined for each case. In addition, the superior squaramide diester gelator was compared with an analogue triazole-based gelator in terms of critical gelation concentration, gelation kinetics and thermal phase transition.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.14.180