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pH‐Responsive Pillar[6]arene‐based Water‐Soluble Supramolecular Hexagonal Boxes
Author(s) -
KaizermanKane Dana,
Hadar Maya,
Tal Noam,
Dobrovetsky Roman,
Zafrani Yossi,
Cohen Yoram
Publication year - 2019
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.201900217
Subject(s) - supramolecular chemistry , pillar , hydrogen bond , trimesic acid , crystallography , hexagonal crystal system , protonation , chemistry , supramolecular assembly , materials science , stereochemistry , nanotechnology , molecule , crystal structure , organic chemistry , ion , structural engineering , engineering
We describe the preparation of the first water‐soluble pH‐responsive supramolecular hexagonal boxes (SHBs) based on multiple charge‐assisted hydrogen bonds between peramino‐pillar[6]arenes 2 with the molecular “lid” mellitic acid ( 1 a ). The interaction between 2 and 1 a , as well as the other “lids” pyromellitic and trimesic acids ( 1 b and 1 c , respecively) were studied by a combination of experimental and computational methods. Interestingly, the addition of 1 a to the complexes of the protonated form of pillar[6]arene 2 , that is, 3 , with bis‐sulfonate 4 a or 4 b , immediately led to guest escape along with the formation of closed 1 a 2 2 supramolecular boxes. Moreover, the process of the openning and closing of the supramolecular boxes along with threading and escaping of the guests, respectively, was found to be reversible and pH‐responsive. This study paves the way for the easy and modular preparation of different SHBs that may have myriad applications.