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
- Chinese Journal of Polymer Science Vol. 41, Issue 5, Pages: 745-759(2023)
- Affiliations：
  
  State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200438, China
- Author bio：
  
  jdding1@fudan.edu.cn
- Funds：
- DOI：10.1007/s10118-023-2930-6
  CLC： M
- Received：30 November 2022，
  
  Revised：2022-12-24，
  
  Accepted：25 December 2022，
  
  Online First：21 February 2023，
  
  Published：01 May 2023
- Accepted：
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Rao, W. H.; Yu, L.; Ding, J. D. Stride strategy to enable a quasi-ergodic search of reaction pathways demonstrated by ring-opening polymerization of cyclic esters.Chinese J. Polym. Sci.2023,41, 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.
Rao, W. H.; Yu, L.; Ding, J. D. Stride strategy to enable a quasi-ergodic search of reaction pathways demonstrated by ring-opening polymerization of cyclic esters.Chinese J. Polym. Sci.2023,41, 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)

-caprolactone (CL)

and

-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).

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references

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