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Issue 1, 2014
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Homochiral Self-Sorting of BINOL Macrocycles

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Abstract

Chiral arylene–ethynylene macrocycles (AEMs) were synthesized via alkyne metathesis-mediated depolymerization of BINOL-based polymers. Homochiral dimers are selectively obtained from metathesis of heterochiral polymers. Thermodynamic analysis and computational modeling suggests the homochiral self-sorting to be entropy-driven due to the greater symmetry of the homochiral dimers over the heterochiral dimer. This symmetry-controlled reaction is a novel approach to achieving high selectivity in dynamic covalent macrocycle synthesis. Importantly, the result describes a new paradigm in dynamic covalent chemistry that will enable efficient synthesis of new chiral architectures.

Graphical abstract: Homochiral Self-Sorting of BINOL Macrocycles

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Supplementary files

Article information


Submitted
18 Jul 2013
Accepted
23 Aug 2013
First published
02 Sep 2013

Chem. Sci., 2014,5, 81-85
Article type
Edge Article

Homochiral Self-Sorting of BINOL Macrocycles

S. W. Sisco and J. S. Moore, Chem. Sci., 2014, 5, 81
DOI: 10.1039/C3SC52018H

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