手性两亲性氧杂杯[2]芳烃[2]三嗪衍生物构建囊泡用于对映选择性识别有机阴离子。
Vesicles Constructed with Chiral Amphiphilic Oxacalix[2]arene[2]triazine Derivatives for Enantioselective Recognition of Organic Anions.
机构信息
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences , Beijing 100190, China.
University of Chinese Academy of Sciences , Beijing 100049, China.
出版信息
ACS Appl Mater Interfaces. 2018 Jan 31;10(4):3181-3185. doi: 10.1021/acsami.7b18723. Epub 2018 Jan 16.
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.
手性两亲性氧杂杯[2]芳烃[2]三嗪衍生物 1-3 带有 l-脯氨酸部分，被合成出来。手性大环两亲分子的自组装行为被研究。SEM、TEM 和 DLS 测量表明，1 形成了稳定的囊泡（约 90nm 大小），而 2 和 3 则形成了胶束。通过 DLS 监测，由 1 组成的囊泡对手性阴离子（2S，3S）-2,3-二羟基丁二酸（d-酒石酸）、S-扁桃酸和 S-（+）樟脑磺酸具有选择性响应，而不是其对映体。DFT 计算表明，手性选择源于手性电子缺空腔与有机阴离子之间的协同阴离子-π 相互作用和氢键。
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