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.
Original language | English (US) |
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Pages (from-to) | 81-85 |
Number of pages | 5 |
Journal | Chemical Science |
Volume | 5 |
Issue number | 1 |
DOIs | |
State | Published - Jan 1 2014 |
ASJC Scopus subject areas
- Chemistry(all)