Temperature-Dependent and pH-Responsive Pillar[5]arene-Based Complexes and Hydrogen-Bond-Based Supramolecular Pentagonal Boxes in Water |
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Authors: | Maya Hadar Dana Kaizerman-Kane Dr Yossi Zafrani Prof Dr Yoram Cohen |
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Institution: | 1. School of Chemistry, Sackler Faculty of Exact Sciences, Tel Aviv University, Ramat Aviv, 69978 Tel Aviv, Israel;2. Department of Organic Chemistry, Israel Institute for Biological Research, Ness-Ziona, 74000 Israel |
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Abstract: | 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-pillar5]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 pillar5]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 1H NMR characteristics of 2 b and 2 c in the cavity of 1 and the SPBs. |
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Keywords: | host–guest systems hydrogen bonds pillar[5]arenes supramolecular boxes supramolecular chemistry water |
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