Vesicles Constructed with Chiral Amphiphilic Oxacalix[2]arene[2]triazine Derivatives for Enantioselective Recognition of Organic Anions
| Autor: | De-Hui Tuo, Yu-Fei Ao, De-Xian Wang, Qing He, Qi-Qiang Wang |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Materials science
biology 010405 organic chemistry Hydrogen bond Vesicle Enantioselective synthesis 010402 general chemistry 01 natural sciences Micelle 0104 chemical sciences chemistry.chemical_compound chemistry Amphiphile Polymer chemistry biology.protein General Materials Science Enantiomer Triazine Organic anion |
| Zdroj: | ACS applied materialsinterfaces. 10(4) |
| ISSN: | 1944-8252 |
| Popis: | Chiral amphiphilic oxacalix[2]arene[2]triazine derivatives 1–3 bearing l-prolinol moieties were synthesized. The self-assembly behavior of the chiral macrocyclic amphiphiles was investigated. SEM, TEM, and DLS measurements demonstrated that 1 formed stable vesicles (size of ∼90 nm), whereas 2 and 3 formed micelles. As monitored by DLS, vesicles composed of 1 showed selective response to the chiral anions (2S, 3S)-2,3-dihydroxysuccinate (d-tartrate), S-mandelate and S-(+)-camphorsulfonate over their enantiomers. DFT calculations revealed that the enantioselectivity arises from cooperative anion-π interactions and hydrogen bonding between the chiral electron-deficient cavity and the organic anions. |
| Databáze: | OpenAIRE |
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