Temperature‐Dependent and pH‐Responsive Pillar[5]arene‐Based Complexes and Hydrogen‐Bond‐Based Supramolecular Pentagonal Boxes in Water

Autor: Yossi Zafrani, Dana Kaizerman-Kane, Maya Hadar, Yoram Cohen
Rok vydání: 2020
Předmět:
Zdroj: Chemistry – A European Journal. 26:11250-11255
ISSN: 1521-3765
0947-6539
DOI: 10.1002/chem.202000972
Popis: Supramolecular systems in water are of paramount importance and those based on hydrogen bonds are both intriguing and scarce. Here, after studying the peculiar host-guest complexes formed between per-dimethylamino-pillar[5]arene (1) and the bis-sulfonates 2 a-c, we describe the formation of the first hydrogen-bond-based supramolecular pentagonal boxes (SPBs), which are stable in water. These pH-responsive SPBs are constructed from 1 as a body, benzene polycarboxylic acids 3 a,b as lid compounds, and 2 a-c as guests. We demonstrate that encapsulation of 2 a-c in pillar[5]arene 1 and in the highly stable water-soluble SPBs, that is, 1(3 a)2 and 1(3 b)2 , is both temperature and pH dependent and, quite interestingly, depends, on the nature of the lid compounds used for capping the boxes even at high pH. We also highlight the difference in the 1 H NMR characteristics of 2 b and 2 c in the cavity of 1 and the SPBs.
Databáze: OpenAIRE
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