Complexation of chiral amines by resorcin[4]arene sulfonic acids in polar media - circular dichroism and diffusion studies of chirality transfer and solvent dependence.

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ID: 76706
2019
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Abstract
Directional self-assembly of conformationally well-defined complexes in polar environment is still a major challenge in supramolecular chemistry. In the present study we demonstrate that resorcin[4]arene sulfonic acid (RSA) interacts with chiral amines (amino acid derivatives and aminocavitands) to form inclusion complexes and capsules based on electrostatic interactions. The complexes were characterized by circular dichroism and DOSY NMR spectroscopy. Chirality transfer from amines onto a resorcinarene skeleton was manifested by the appearance of signals in CD spectra and diastereotopic splitting in NMR spectra. The complexes proved to be thermodynamically stable in methanol, but DMSO and methanol/water mixtures were found to be highly disintegrative for these complexes. This result is quite non-intuitive and worth attention in the context of formation of supramolecular complexes in polar environment, for which DMSO is most often a first-choice solvent.
Reference Key
setner2019complexationbeilstein Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Setner, Bartosz;Szumna, Agnieszka;
Journal Beilstein journal of organic chemistry
Year 2019
DOI
10.3762/bjoc.15.187
URL
https://doi.org/10.3762/bjoc.15.187
Keywords
self-assembly chirality supramolecular chemistry cavitands macrocycle resorcin[4]arene

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