Loading...
Please wait, while we are loading the content...
Intra- and intermolecular hydrogen bonds enhance the fluoride-responsiveness of functionalized glycolipid-based gelators.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Tsai, Cheng-Che Chuang, Wei-Tsung Tsai, Yow-Fu Li, Jyun-Ting Liao, Chun-Chen |
| Copyright Year | 2013 |
| Abstract | We propose a facile approach toward enhancing the efficiency of fluoride-responsive gels through the positioning of functionalized receptor units, allowing tunable intra- and intermolecular hydrogen bonding, in the gelator molecules. We prepared the new glycolipid-based gelator 2 and its hydroxy and methoxy derivatives 2a and 2b, respectively, to study the effects of three types modes of supramolecular assembly: solely intermolecular hydrogen bonding in 2, solely intramolecular hydrogen bonding in 2b, and both inter- and intramolecular hydrogen bonding in 2a. 1H NMR spectra confirmed the self-assembly interactions of these glycolipid-based gelators. We measured the minimum gel concentrations and sol-gel transitions and recorded X-ray diffraction patterns and electron micrographs to characterize the gelation behavior and structural organization of each of these supramolecular gels. Among these three gelators, only 2 and 2a could form organogels in the test solvents, indicating that intermolecular hydrogen bonding plays a determinant role in the supramolecular assemblies leading to gelation. The self-assembly of 2 resulted in a bilayer-packed lamellar structure within ribbon-like fibers, whereas that of 2a resulted in hexagonally packed cylindrical micelles within tree-like fibers. A minimum amount of 0.3 equivalent of F- was required for complete disruption of the gel formed from 2a, which was approximately four times lower than that required for the gel formed from 2. Thus, the incorporation of a β-hydroxy motif-the only difference in the chemical structures of 2 and 2a-led to interesting variations in the resulting gel morphologies and enhanced the gel's fluoride-responsiveness. |
| Starting Page | 819 |
| Ending Page | 827 |
| Page Count | 9 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/C2TB00150K |
| PubMed reference number | 32260740 |
| Journal | Medline |
| Volume Number | 1 |
| Issue Number | 6 |
| Alternate Webpage(s) | http://www.rsc.org/suppdata/tb/c2/c2tb00150k/c2tb00150k.pdf |
| Alternate Webpage(s) | https://doi.org/10.1039/C2TB00150K |
| Journal | Journal of materials chemistry. B |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
