Expanding the limits of amide–triazole isosteric substitution in bisamide-based physical gels. Issue 36 (3rd July 2019)

• Record Type: Journal Article
• Authors: Tautz, Markus; Torras, Juan; Grijalvo, Santiago; Eritja, Ramón; Saldías, César; Alemán, Carlos; Díaz, David Díaz
• Is Part Of: RSC advances. Volume 9:Issue 36(2019)
• Page Start: 20841
• Page End: 20851
• Publication Date: 2019-07-03
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9ra03316e
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Dual amide–triazole isosteric substitution in a bis-amide gelator allows fine-tuning of the properties of the corresponding supramolecular gels. Abstract : Gelation of organic solvents using N, N ′-((1 S, 2 S )-cyclohexane-1, 2-diyl)didodecanamide (C12 –Cyc ) is driven by its self-assembly via antiparallel hydrogen bonds and van der Waals intermolecular interactions. In this work we carried out a dual isosteric substitution of the two amide groups with 1, 2, 3-triazole rings affording the corresponding isosteric gelator (click-C12 –Cyc ). A detailed comparative study in terms of the gelation ability and gel properties demonstrated that the 1, 2, 3-triazoles can take over all of the functions derived from the amide groups offering a versatile strategy for tuning the properties of the corresponding gels. This is not an obvious outcome because the directional amide groups inC12 –Cyc constitute the source of the hydrogen bonds to build the 3D self-assembled network. Furthermore, theoretical calculations revealed thatclick-C12 –Cyc can adopt a wide variety of interacting patterns, whose relative stability depends on the polarity of the environment, this is in good agreement with the experimental data obtained regarding its gelation ability. Other important features ofclick-C12 –Cyc for potential practical applications are its non-cytotoxic character and its phase-selective gelation of water–oil mixtures.