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

Alegre-Requena, J.V. ; Haring, M. ; Sonsona, I.G. ; Abramov, A. ; Marques-Lopez, E. (Universidad de Zaragoza) ; Pérez Herrera, R. (Universidad de Zaragoza) ; Diaz Diaz, D.

Resumen: 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.

Idioma: Inglés

DOI: 10.3762/bjoc.14.180

Año: 2018

Publicado en: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 14 (2018), 2065-2073
ISSN: 1860-5397

Factor impacto JCR: 2.595 (2018)

Categ. JCR: CHEMISTRY, ORGANIC rank: 20 / 57 = 0.351 (2018) - Q2 - T2

Factor impacto SCIMAGO: 0.821 - Organic Chemistry (Q2)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E07-17R
Financiación: info:eu-repo/grantAgreement/ES/MINECO/CTQ2017-88091-P

Tipo y forma: Artículo (Versión definitiva)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)