Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 16, Pages 5302-5306Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201900217
Keywords
mellitic acid; molecular box; multivalency; pillar[6]arene; supramolecular chemistry
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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 pillarlojarene 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.
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