Organogel Formation by Coaggregation of Adaptable Amidocarbamates and Their Tetraamide Analogues
- 14 June 2005
- journal article
- Published by American Chemical Society (ACS) in Langmuir
- Vol. 21 (15), 6776-6787
- https://doi.org/10.1021/la050655j
Abstract
Mixtures of derivatives of Hanabusa's bolaamphiphilic amidocarbamates containing two Z-valinyl subunits and aliphatic spacers that range from ethylenic to octamethylenic are able to form organogels. A coassembly of them is observed in their acetonitrile and toluene gels; namely, the concentration of a given compound at which a gel is formed is lowered by the presence of equimolar quantities of any other compound in the series. The aggregates were studied by wide-angle X-ray diffraction (WAXD) and the results can be rationalized if the gel fibers are formed by supramolecular copolymers. NMR studies reveal that in solution these molecules adopt folded conformations containing intramolecular H-bonds, but IR studies indicate that these are not present in their aggregates. Additionally, analogues of the amidocarbamates obtained by replacement of the carbamate functionality by amide have been shown to behave in a similar way. For these molecules it can be shown that the central aliphatic subunit is not completely extended in the conformations present in the aggregates according to IR and WAXD studies. The tetraamide-type compounds described are robust organogelators that form gels in a variety of organic solvents with good thermostability and present improved feasibility for the synthesis of envisaged functional organogelators.Keywords
This publication has 31 references indexed in Scilit:
- Fabrication and Optical Properties of Erbium‐Doped Germanium NanowiresAdvanced Materials, 2004
- Self-Assembly of Small Peptidomimetic CyclophanesChemistry – A European Journal, 2004
- Ion-Driven ATP Pump by Self-Organized Hybrid Membrane MaterialsJournal of the American Chemical Society, 2004
- Two-Component Dendritic Gels: Easily Tunable MaterialsJournal of the American Chemical Society, 2003
- Efficient Macrocyclization of U-Turn Preorganized Peptidomimetics: The Role of Intramolecular H-Bond and Solvophobic EffectsJournal of the American Chemical Society, 2003
- Gelation‐Assisted Light Harvesting by Selective Energy Transfer from an Oligo(p‐phenylenevinylene)‐Based Self‐Assembly to an Organic DyeAngewandte Chemie-International Edition, 2003
- Conformational and Thermal Phase Behavior of Oligomethylene Chains Constrained by Carbohydrate Hydrogen-Bond NetworksJournal of the American Chemical Society, 2000
- 1H NMR Investigation of the Composition, Structure, and Dynamics of Cholesterol−Stilbene Tethered Dyad OrganogelsLangmuir, 2000
- Excellent gelators for organic fluids: Simple bolaform amides derived from amino acidsAdvanced Materials, 1997
- Quasi-equilibration of N(a) + 1/2H2 .dblharw. NH established on c(2 .times. 2)-nitrogen of the palladium(100), rhodium(100), and platinum-rhodium(100) surfaces during hydrogenation of c(2 .times. 2)-nitrogenJournal of the American Chemical Society, 1991