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Self‐Assembly and Disassembly of Vesicles as Controlled by Anion–π Interactions
Author(s) -
He Qing,
Ao YuFei,
Huang ZhiTang,
Wang DeXian
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201504710
Subject(s) - supramolecular chemistry , vesicle , amphiphile , chemistry , non covalent interactions , self assembly , ion , sodium , crystallography , molecule , hydrogen bond , organic chemistry , crystal structure , membrane , biochemistry , copolymer , polymer
Anion–π interactions have been widely studied as new noncovalent driving forces in supramolecular chemistry. However, self‐assembly induced by anion–π interactions is still largely unexplored. Herein we report the formation of supramolecular amphiphiles through anion–π interactions, and the subsequent formation of self‐assembled vesicles in water. With the π receptor 1 as the host and anionic amphiphiles, such as sodium dodecylsulfate (SDS), sodium laurate (SLA), and sodium methyl dodecylphosphonate (SDP), as guests, the sequential formation of host–guest supramolecular amphiphiles and self‐assembled vesicles was demonstrated by SEM, TEM, DLS, and XRD techniques. The intrinsic anion–π interactions between 1 and the anionic amphiphiles were confirmed by crystal diffraction, HRMS analysis, and DFT calculations. Furthermore, the controlled disassembly of the vesicles was promoted by competing anions, such as NO 3 − , Cl − , and Br − , or by changing the pH value of the medium.