pH-Responsive Pillar[6]arene-based Water-Soluble Supramolecular Hexagonal Boxes

Dana Kaizerman-Kane, Maya Hadar, Noam Tal, Roman Dobrovetsky, Yossi Zafrani*, Yoram Cohen

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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-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.

Original languageEnglish
Pages (from-to)5302-5306
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number16
DOIs
StatePublished - 8 Apr 2019

Keywords

  • mellitic acid
  • molecular box
  • multivalency
  • pillar[6]arene
  • supramolecular chemistry

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