3 years ago

Vesicles Constructed with Chiral Amphiphilic Oxacalix[2]arene[2]triazine Derivatives for Enantioselective Recognition of Organic Anions

Vesicles
Constructed with Chiral Amphiphilic Oxacalix[2]arene[2]triazine Derivatives
for Enantioselective Recognition of Organic Anions
Yu-Fei Ao, De-Xian Wang, De-Hui Tuo, Qi-Qiang Wang, Qing He
Chiral amphiphilic oxacalix[2]arene[2]triazine derivatives 13 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.

Publisher URL: http://dx.doi.org/10.1021/acsami.7b18723

DOI: 10.1021/acsami.7b18723

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