Biodegradable Polyhydroxyalkanoates by Stereoselective Copolymerization of Racemic Diolides: Stereocontrol and Polyolefin-Like Properties.

Xiaoyan Tang, Andrea H Westlie, Lucia Caporaso, Luigi Cavallo, Laura Falivene, Eugene Y-X Chen

Angewandte Chemie (International ed. in English) 2020 May 11

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Bacterial polyhydroxyalkanoates (PHAs) are a unique class of biodegradable polymers because of their biodegradability in ambient environments and structural diversity enabled by side-chain groups. However, the biosynthesis of PHAs is slow and expensive, limiting their broader applications as commodity plastics. To overcome such limitation, the catalyzed chemical synthesis of bacterial PHAs has been developed, using the metal-catalyzed stereoselective ring-opening (co)polymerization of racemic cyclic diolides (rac-8DLR , R=alkyl group). In this combined experimental and computational study, polymerization kinetics, stereocontrol, copolymerization characteristics, and the properties of the resulting PHAs have been examined. Most notably, stereoselective copolymerizations of rac-8DLMe with rac-8DLR (R=Et, Bu) have yielded high-molecular-weight, crystalline isotactic PHA copolymers that are hard, ductile, and tough plastics, and exhibit polyolefin-like thermal and mechanical properties. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Xiaoyan Tang, Andrea H Westlie, Lucia Caporaso, Luigi Cavallo, Laura Falivene, Eugene Y-X Chen. Biodegradable Polyhydroxyalkanoates by Stereoselective Copolymerization of Racemic Diolides: Stereocontrol and Polyolefin-Like Properties. Angewandte Chemie (International ed. in English). 2020 May 11;59(20):7881-7890