4.7 Article

Controlled Ring-Opening Polymerization of β-Butyrolactone Via Bifunctional Organoboron Catalysts

Journal

MACROMOLECULES
Volume 54, Issue 12, Pages 5509-5517

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.macromol.1c00250

Keywords

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Funding

  1. Zhejiang Provincial Natural Science Foundation of China [R21B040004]
  2. National Natural Science Foundation of China [51973186, 91956123]

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The study explored a series of bifunctional organoboron catalysts with varying frameworks and nucleophiles for preparing PHBs, and the optimized catalyst achieved ideal reactivity with an excellent polymer selectivity (>99%) in a controlled manner.
Ring-opening polymerization affords an efficient strategy to convert beta-butyrolactone into poly(beta-hydroxybutyrate) (PHB) which is a promising and widely used biodegradable polyester. Although numerous metallic catalysts have been well established, the toxic residual metal contaminants of them impede the application of PHBs especially in the biomedical and microelectronic field. Herein, we explore a series of bifunctional organoboron catalysts with varying frameworks and nucleophiles for preparing PHBs. The modular design of these well-defined catalysts permits synthetically facile steric and electronic interference to systematically optimize catalytic activity. The optimized catalyst achieved ideal reactivity with an excellent polymer selectivity (>99%) in a controlled manner. It was further confirmed that the BBL ring is opened at the alkyl-oxygen bond with the concomitance of the inversion of chiral centers, resulting in polyesters terminated by carboxylate. Additionally, side reactions were comprehensively investigated and a mechanism was proposed.

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