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Controllable Synthesis of Heterofunctionalized Polyethers via Intramolecular Phosphonium Bisborane Lewis Pair-Catalyzed Immortal Ring-Opening Polymerization

Xiaowu Wang, Minmin Shi, Jiwen Hui, Xinhui Kou, Wang Jiansen, Rong‐Lin Zhong, Zhibo Li

2023Macromolecules25 citationsDOI

Abstract

A metal-free phosphonium bisborane Lewis pair ( PBB-Br ) was demonstrated to realize the immortal ring-opening polymerization (iROP) of propylene oxide (PO) under mild conditions with alcohols as chain-transfer agents (CTAs). Narrow dispersed poly(propylene oxides) (PPOs) with controllable molecular weights predicted from the [PO] 0 /([ PBB-Br ] 0 + [CTAs] 0 ) molar ratio were obtained in quantitative conversion. These findings indicated the iROP feature of PBB-Br -catalyzed PO polymerization. The rapid, reversible, and quantitative chain transfer assured the iROP characteristic for an intramolecular Lewis pair catalyst PBB-Br, so various well-defined heterofunctionalized PPOs were easily produced. All the α,ω-difunctionalized PPOs were carefully characterized. Density functional theory (DFT) calculations reveal that the chain transfer to the CTA process is almost barrierless (0.8 kcal mol –1 ) and thermodynamically favorable as compared to chain propagation. Moreover, PPO-based block copolyethers were easily obtained in one-pot using epoxide mixtures. This research demonstrated that the delicately designed intramolecular synergistic Lewis pair offered a powerful and controllable method to prepare various heterofunctionalized PPO samples with high values.

Topics & Concepts

Propylene oxideIntramolecular forcePhosphoniumPolymerizationPolymer chemistryChemistryEpoxideLewis acids and basesChain transferChain terminationCatalysisChain propagationRing (chemistry)Anionic addition polymerizationCopolymerRadical polymerizationOrganic chemistryPolymerEthylene oxideOrganoboron and organosilicon chemistrySynthetic Organic Chemistry MethodsCarbon dioxide utilization in catalysis
Controllable Synthesis of Heterofunctionalized Polyethers via Intramolecular Phosphonium Bisborane Lewis Pair-Catalyzed Immortal Ring-Opening Polymerization | Litcius