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Zhang Q, Catti L, Kaila VRI, et al. To catalyze or not to catalyze: elucidation of the subtle differences between the hexameric capsules of pyrogallolarene and resorcinarene. Chem Sci. 2016;8(2):1653-1657doi: 10.1039/c6sc04565k.
Zhang, Q., Catti, L., Kaila, V. R. I., & Tiefenbacher, K. (2017). To catalyze or not to catalyze: elucidation of the subtle differences between the hexameric capsules of pyrogallolarene and resorcinarene. Chemical science, 8(2), 1653-1657. https://doi.org/10.1039/c6sc04565k
Zhang, Qi, et al. "To catalyze or not to catalyze: elucidation of the subtle differences between the hexameric capsules of pyrogallolarene and resorcinarene." Chemical science vol. 8,2 (2017): 1653-1657. doi: https://doi.org/10.1039/c6sc04565k
Zhang Q, Catti L, Kaila VRI, Tiefenbacher K. To catalyze or not to catalyze: elucidation of the subtle differences between the hexameric capsules of pyrogallolarene and resorcinarene. Chem Sci. 2017 Feb 01;8(2):1653-1657. doi: 10.1039/c6sc04565k. Epub 2016 Nov 15. PMID: 28451294; PMCID: PMC5364520.
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Chem Sci. 2017 Feb 01;8(2):1653-1657. doi: 10.1039/c6sc04565k. Epub 2016 Nov 15.

To catalyze or not to catalyze: elucidation of the subtle differences between the hexameric capsules of pyrogallolarene and resorcinarene.

Chemical science

Qi Zhang, Lorenzo Catti, Ville R I Kaila, Konrad Tiefenbacher

Affiliations

  1. Department of Chemistry , University of Basel , St. Johannsring 19 , CH-4056 Basel , Switzerland . Email: [email protected].
  2. Department of Chemistry , Technical University of Munich , Lichtenbergstrasse 4 , 85747 Garching , Germany.
  3. Department of Biosystems Science and Engineering , ETH Zürich , Mattenstrasse 26 , CH-4058 Basel , Switzerland . Email: [email protected].

PMID: 28451294 PMCID: PMC5364520 DOI: 10.1039/c6sc04565k

Abstract

The closely related, self-assembled resorcinarene and pyrogallolarene capsules display contrasting and puzzling encapsulation behaviors. Herein, we elucidate the reasons for these differences by combining experimental studies and DFT calculations. Furthermore, we report that, in contrast to the resorcinarene capsule, the pyrogallolarene derivative is not capable of catalyzing reactions with cationic transition states. The molecular mechanisms responsible for these observations are probed in detail.

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