Stride Strategy to Enable a Quasi-ergodic Search of Reaction Pathways Demonstrated by Ring-opening Polymerization of Cyclic Esters

Wei-Han Rao; Lin Yu; Jian-Dong Ding

doi:10.1007/s10118-023-2930-6

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Stride Strategy to Enable a Quasi-ergodic Search of Reaction Pathways Demonstrated by Ring-opening Polymerization of Cyclic Esters

RESEARCH ARTICLE | Updated：2023-04-21

- Stride Strategy to Enable a Quasi-ergodic Search of Reaction Pathways Demonstrated by Ring-opening Polymerization of Cyclic Esters
- Stride Strategy to Enable a Quasi-ergodic Search of Reaction Pathways Demonstrated by Ring-opening Polymerization of Cyclic Esters
- 高分子科学（英文版） 2023年41卷第5期页码：745-759
- Affiliations：
  
  1.State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200438, China
- Author bio：
  
  jdding1@fudan.edu.cn
- Funds：
  
  The work was financially supported by the National Natural Science Foundation of China (No. 52130302). We thank Prof. Xin Xu, Prof. Zhenhua Li, and Prof. Junpo He for their critical reading of our manuscript.;Electronic supplementary information (ESI) is available free of charge in the online version of this article athttp://doi.org/10.1007/s10118-023-2930-6.
- DOI：10.1007/s10118-023-2930-6
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Stride Strategy to Enable a Quasi-ergodic Search of Reaction Pathways Demonstrated by Ring-opening Polymerization of Cyclic Esters[J]. 高分子科学（英文版）, 2023,41(5):745-759.

Wei-Han Rao, Lin Yu, Jian-Dong Ding. Stride Strategy to Enable a Quasi-ergodic Search of Reaction Pathways Demonstrated by Ring-opening Polymerization of Cyclic Esters[J]. Chinese Journal of Polymer Science, 2023,41(5):745-759.
Stride Strategy to Enable a Quasi-ergodic Search of Reaction Pathways Demonstrated by Ring-opening Polymerization of Cyclic Esters[J]. 高分子科学（英文版）, 2023,41(5):745-759. DOI： 10.1007/s10118-023-2930-6.

Wei-Han Rao, Lin Yu, Jian-Dong Ding. Stride Strategy to Enable a Quasi-ergodic Search of Reaction Pathways Demonstrated by Ring-opening Polymerization of Cyclic Esters[J]. Chinese Journal of Polymer Science, 2023,41(5):745-759. DOI： 10.1007/s10118-023-2930-6.

摘要

Ergodicity is essentially important for research of reaction mechanism, yet hard to achieve in the formalism of DFT calculation. The stride strategy helps to discover new landscapes involving the omitted reaction pathways and enabling the quasi-ergodic search of reaction pathways to obtain the globally minimum barrier. The strategy was employed to establish a satisfactory structure-reactivity relationship for ring-opening polymerization of cyclic monomers.

Abstract

Coordination-insertion ring-opening polymerization (ROP) of cyclic esters is an industrial way to synthesize polyesters, which are widely applied in biomedical and environment-benign fields. However, the rate-determining transition state (TS) identified by the conventional reaction pathways (pathway A and pathway B) presented in the literature did not well describe the structure-reactivity relationship. The misidentification of the rate-determining TS might arise from the less ergodicity in the search of reaction pathways. Herein, we suggested a stride strategy based on the insight that even a partial double bond is rotatable at the catalysis temperature. As a result, we revealed a new reaction pathway, pathway C with a torsion transition state TSC2, by density functional theory (DFT). We also carried out kinetic experiments of ROP of D-lactide (D-LA), L-lactide (L-LA),ε,-caprolactone (CL), and,δ,-valerolactone (VL), using poly(ethylene glycol) as the initiator and stannous octoate as the catalyst. The excellent linearity between the calculated free energy barriers and logarithms of the experimental kinetic constants of the two kinds of lactide and lactone monomers, was established, validating the quasi-ergodic search of reaction pathways and the scaling predicted by transition state theory. The linearity was highly predictive for the other lactide and lactone monomers, demonstrated by glycolide (GA) and trimethylene urethane (TU).

关键词

Keywords

Coordination-insertion mechanismRing-opening polymerizationDensity functional theoryBiodegradable polymerLactideLactoneCyclic ester

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