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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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
Full Research Paper
Gelation
Gels
Glutamic acid
glutamic acid derivative
Infrared spectroscopy
organogel
Phase transitions
Rheology
Self-assembly
squaramide
supramolecular gel
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cited_by cdi_FETCH-LOGICAL-c475t-b6278ee0e467b1c7e6d21b2d2b0cc6ca5dd62202f0bb4f71519710e3c0e485cd3
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container_issue 1
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container_title Beilstein journal of organic chemistry
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creator Alegre-Requena, Juan V
Häring, Marleen
Sonsona, Isaac G
Abramov, Alex
Marqués-López, Eugenia
Herrera, Raquel P
Díaz Díaz, David
description 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.
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subjects Acids
Catalysis
Chemistry
Cooling
Electron microscopy
Full Research Paper
Gelation
Gels
Glutamic acid
glutamic acid derivative
Infrared spectroscopy
organogel
Phase transitions
Rheology
Self-assembly
squaramide
supramolecular gel
title Synthesis and supramolecular self-assembly of glutamic acid-based squaramides
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