Self-Assembly of Octaaminoamido Derivatives of Resorcin[4]arene in Water − A "Cell-Like" Submicron-Scale Hydrogel Structure

• Published in: European journal of organic chemistry Vol. 2004; no. 15; pp. 3323 - 3329
• Main Authors: Kazakova, Ella K., Morozova, Julia E., Prosvirkin, Alexander V., Pich, Andrij Z., Gubanov, Eduard P., Muslinkin, Abdurakhim A., Habicher, Wolf D., Konovalov, Alexander I.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.08.2004; WILEY‐VCH Verlag; Wiley
• Subjects: Calixarenes; Chemistry; Chemistry, Organic; Gels; Nanostructures; Physical Sciences; Science & Technology; Self-assembly; MOLECULAR DESIGN; self-assembly; GELATION PROCESS; calixarenes; GELATORS; gels; nanostructures; COMPLEXATION; GEL
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200400124

We have prepared four new octaaminoamide resorcin[4]arenes having hydrocarbon chains of different lengths (1, 2: R = CH3; 3, 4: R = C11H23) and different terminal groups (1, 3: NH2; 2, 4: NMe2). The surface tension and self‐assembly of aqueous solutions of 2−4 were studied and their critical micelle concentrations (CMC) were determined. At the water/air interface, compound 2 forms a multilayer structure, whereas compound 3 forms a bilayer and compound 4 a monolayer structure. In addition, we found that compound 3 has a second CMC (CMC2). A dynamic light scattering study indicated that, at a concentration of 0.1 wt% (i.e., > CMC2), 3 forms nanodimensional aggregates; increasing the concentration up to 1.2 wt% results in the formation of strong transparent gels. For hydrogels having 5 wt% of 3, SEM images demonstrated the formation of submicron‐scale “cell‐like” aggregates. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)