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A Self‐Assembled Cage for Wide‐Scope Chiral Recognition in Water
Author(s) -
Wu Guangcheng,
Chen Yixin,
Fang Shuai,
Tong Lu,
Shen Libo,
Ge Chenqi,
Pan Yuanjiang,
Shi Xiangli,
Li Hao
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202104164
Subject(s) - cage , chemistry , self assembly , crystallography , circular dichroism , octahedron , hydrogen bond , molecular recognition , enantiomer , stereochemistry , crystal structure , molecule , organic chemistry , mathematics , combinatorics
Herein, we report the self‐assembly of an anionic homochiral octahedral cage by condensing six Ga 3+ cations and four trisacylhydrazone ligands. The robust nature of the hydrazone bond renders the cage stable in water, where it can take advantage of the hydrophobic effect for host–guest recognition. In addition to the internal binding site, namely, the inner cavity, the octahedral cage possesses four “windows”, each of which represents an external binding site allowing peripheral complexation. These internal and external binding sites endow the cage with the capability to bind a broad range of guests whose sizes could either be smaller than or exceed the volume of the cage′s inner cavity. Upon accommodation of a chiral guest, one of the two cage enantiomers becomes more favored than the other, producing circular‐dichroism (CD) signals. The CD signal intensity of the cage is observed to be proportional to the ee value of the chiral guest, allowing a quantitative determination of the latter.