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pH‐Responsive Pillar[6]arene‐based Water‐Soluble Supramolecular Hexagonal Boxes
Authors:Dana Kaizerman‐Kane  Maya Hadar  Noam Tal  Roman Dobrovetsky  Yossi Zafrani  Yoram Cohen
Abstract:We describe the preparation of the first water‐soluble pH‐responsive supramolecular hexagonal boxes (SHBs) based on multiple charge‐assisted hydrogen bonds between peramino‐pillar6]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 pillar6]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 a22 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.
Keywords:Mellitsä  ure  Molekulare Boxen  Multivalenz     Pillar[6]arene  Supramolekulare Chemie
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