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Issue 79, 2019
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Self-sorting in dynamic disulfide assembly: new biphenyl-bridged “nanohoops” and unsymmetrical cyclophanes

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Abstract

We expand on our approach combining dynamic covalent self-assembly and sulfur extrusion to synthesize new biphenyl-linked disulfide and thioether macrocycles, which are variants of the venerable phenyl-bridged paracyclophanes. We then advance this strategy further to use two different thiols in tandem to provide new, elusive unsymmetrical disulfides which can also be trapped as unsymmetrical thioether “nanohoops”. This approach enables substantial amplification of two unsymmetrical trimers out of a library of at least 21 possible macrocycles of various sizes.

Graphical abstract: Self-sorting in dynamic disulfide assembly: new biphenyl-bridged “nanohoops” and unsymmetrical cyclophanes

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Publication details

The article was received on 22 Aug 2019, accepted on 05 Sep 2019 and first published on 13 Sep 2019


Article type: Communication
DOI: 10.1039/C9CC06503B
Chem. Commun., 2019,55, 11840-11843

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    Self-sorting in dynamic disulfide assembly: new biphenyl-bridged “nanohoops” and unsymmetrical cyclophanes

    N. Phan, E. P. K. L. Choy, L. N. Zakharov and D. W. Johnson, Chem. Commun., 2019, 55, 11840
    DOI: 10.1039/C9CC06503B

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