Supramolecular chirogenesis in zinc porphyrins by enantiopure hemicucurbit[n]urils (n = 6, 8)

Lukas Ustrnul; Sandra Kaabel; Tatsiana Burankova; Jevgenija Martõnova; Jasper Adamson; Nele Konrad; Peeter Burk; Victor Borovkov; Riina Aav

doi:10.1039/C9CC07150D

Supramolecular chirogenesis in zinc porphyrins by enantiopure hemicucurbit[n]urils (n = 6, 8)†

Lukas Ustrnul,

^a Sandra Kaabel,

^a Tatsiana Burankova,^b Jevgenija Martõnova,^a Jasper Adamson,

^c Nele Konrad,^a Peeter Burk,

^d Victor Borovkov

*^ae and Riina Aav

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia
E-mail: riina.aav@taltech.ee

^b Paul Scherrer Institute, Laboratory for Neutron Scattering and Imaging, Forschungsstrasse 111, 5232 Villigen PSI, Switzerland

^c National Institute of Chemical Physics and Biophysics, Akadeemia tee 23, 12618 Tallinn, Estonia

^d Faculty of Science and Technology, University of Tartu, Vanemuise 46-208, 51014 Tartu, Estonia

^e College of Chemistry and Materials Science, South-Central University for Nationalities, 182# Minzu RD, Hongshan District, Wuhan, Hubei Province 430074, China
E-mail: victor.borovkov@scuec.edu.cn

Abstract

Chiral cyclohexanohemicucurbit[n]urils (n = 6, 8) (cycHCs) are able to bind guests through multiple “outer surface interactions”, which in the case of planar zinc porphyrins leads to induction of chirality. Crystal structures of complexes of complementary sized hosts revealed social self-sorting, while in the solution phase one cycHC can accommodate up to three porphyrin molecules with log K_total 9.

This article is part of the themed collection: Cucurbiturils and related cavitands

Article information

https://doi.org/10.1039/C9CC07150D

Article type

Communication

Submitted

12 sep 2019

Accepted

12 nov 2019

First published

16 nov 2019

This article is Open Access

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Chem. Commun., 2019,55, 14434-14437

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Supramolecular chirogenesis in zinc porphyrins by enantiopure hemicucurbit[n]urils (n = 6, 8)

L. Ustrnul, S. Kaabel, T. Burankova, J. Martõnova, J. Adamson, N. Konrad, P. Burk, V. Borovkov and R. Aav, Chem. Commun., 2019, 55, 14434 DOI: 10.1039/C9CC07150D

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Chemical Communications

Supramolecular chirogenesis in zinc porphyrins by enantiopure hemicucurbit[n]urils (n = 6, 8)†

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Supramolecular chirogenesis in zinc porphyrins by enantiopure hemicucurbit[n]urils (n = 6, 8)

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