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Issue 10, 2014
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Copolymerization of CO2 and meso epoxides using enantioselective β-diiminate catalysts: a route to highly isotactic polycarbonates

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Abstract

We report a new class of catalysts for the enantioselective copolymerization of CO2 and alicyclic meso epoxides. C1-Symmetric β-diiminate zinc catalysts were designed on the basis of mechanistic information and subsequently optimized using structure–activity relationships and iterative ligand design. The optimized catalysts yield highly isotactic poly(cyclohexene carbonate) and poly(cyclopentene carbonate) with units of up to 94% ee under mild conditions. A diblock copolymer of CO2/cyclohexene oxide and CO2/cyclopentene oxide was synthesized, demonstrating the controlled behaviour of the catalyst. Solid-state structures and solution-state dynamics of the catalyst were studied to explain trends in enantioselectivities and turnover frequencies. A strong correlation between the isotacticity of the polymer and its melting temperature was observed. X-ray powder diffraction was used to measure crystallinity and study the changes in morphology observed upon annealing.

Graphical abstract: Copolymerization of CO2 and meso epoxides using enantioselective β-diiminate catalysts: a route to highly isotactic polycarbonates

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Publication details

The article was received on 06 Jun 2014, accepted on 24 Jun 2014 and first published on 23 Jul 2014


Article type: Edge Article
DOI: 10.1039/C4SC01686F
Chem. Sci., 2014,5, 4004-4011

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    Copolymerization of CO2 and meso epoxides using enantioselective β-diiminate catalysts: a route to highly isotactic polycarbonates

    W. C. Ellis, Y. Jung, M. Mulzer, R. Di Girolamo, E. B. Lobkovsky and G. W. Coates, Chem. Sci., 2014, 5, 4004
    DOI: 10.1039/C4SC01686F

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