Catalyst‐Sidearm‐Induced Stereoselectivity Switching in Polymerization of a Racemic Lactone for Stereocomplexed Crystalline Polymer with a Circular Life Cycle

Zhu, Jian‐Bo; Chen, Eugene Y.‐X.

doi:10.1002/ange.201813006

Cited by 29 publications

(7 citation statements)

References 52 publications

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“…Additionally, other homostereocomplexes have been reported for a few renewable polymers such as poly(propylene succinate), 142 tartaric acid derived polyamides, [403][404][405] poly(propylene carbonate), 406 poly(limonene carbonate) 407,408 and an infinitely recyclable trans-cyclohexyl-ring-fused γ-butyrolactone polymer. 409,410 A particularly interesting example of alternative stereocomplexes are heterostereocomplexes which are materials formed between degradable polymers possessing different backbone architectures. 411 Heterostereocomplexes of PHBs and PLLA were recently investigated and such complexes feature enhanced thermal properties.…”

Section: Pla and Other Degradable Polymersmentioning

confidence: 99%

Stereochemical enhancement of polymer properties

et al. 2019

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The importance of stereochemistry to the function of molecules is generally well understood. However, to date, control over stereochemistry and its potential to influence properties of the resulting polymers are, as yet, not fully realised. This review focuses on the state-of-the-art with respect to how stereochemistry in polymers has been used to influence and control their physical and mechanical properties as well as begin to control their function. A brief overview of the synthetic methodology by which to access these materials is included, with the main focus directed towards stereochemical control over properties such as mechanical, biodegradation and conductivity. Additionally, the advances being made towards enantioseparation, enantioselective catalyst supports and stereo-directed transitions are discussed. Finally, we also consider the opportunities that the rich stereochemistry of sustainably-sourced monomers could offer in this field. Where possible, parallels and general design principles are drawn together to identify opportunities and limitations that these approaches may present in their effects on materials properties, performance and function.

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Section: Pla and Other Degradable Polymersmentioning

confidence: 99%

Stereochemical enhancement of polymer properties

et al. 2019

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“…However, poly(GBL) performance properties are insufficient for common applications. To address this depolymerizability/performance trade-off, ring-fused bicyclic GBL structural derivatives were designed to enhance monomer polymerizability as well as polymer thermal stability and crystallinity without compromising the full chemical recyclability (10,19), but the resulting crystalline materials with high melting transition temperatures (T m ) are mechanically brittle, thus requiring incorporation of flexible copolymers to reach useful ductility (20). In addition, to afford these crystalline materials demands either stereocomplexation of the preformed enantiomeric polymers from separate pools of enantiopure monomers or the elaborate stereoselective polymerization of the racemic monomer pool.…”

Section: Introductionmentioning

confidence: 99%

High-performance pan-tactic polythioesters with intrinsic crystallinity and chemical recyclability

et al. 2020

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Three types of seemingly unyielding trade-offs have continued to challenge the rational design for circular polymers with both high chemical recyclability and high-performance properties: depolymerizability/performance, crystallinity/ductility, and stereo-disorder/crystallinity. Here, we introduce a monomer design strategy based on a bridged bicyclic thiolactone that produces stereo-disordered to perfectly stereo-ordered polythiolactones, all exhibiting high crystallinity and full chemical recyclability. These polythioesters defy aforementioned trade-offs by having an unusual set of desired properties, including intrinsic tacticity-independent crystallinity and chemical recyclability, tunable tacticities from stereo-disorder to perfect stereoregularity, as well as combined high-performance properties such as high thermal stability and crystallinity, and high mechanical strength, ductility, and toughness.

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“…The depolymerization of other derivatives such as P(3,4-T6L), P(4,5-T6L) and it-PCBL, ht-PCBL also showed similar behaviours [73,120,122,123]. Compared with thermal recycling of related polymers in bulk at high temperatures, the depolymerization process was more favourable using catalysts in toluene.…”

Section: Other Polymerization Methodologies For γ-Lactonesmentioning

confidence: 89%

Ring-opening polymerization of γ-lactones and copolymerization with other cyclic monomers

Song

Pascouau

Zhao

et al. 2020

Progress in Polymer Science

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Triggered by raised environmental awareness and the rising requirements for sustainable polymers such as degradable or recyclable polymers, studies on ring-opening (co)polymerization (ROP/ROCP) of (bio-based) cyclic monomers (e.g., cyclic esters, lactides, epoxides etc.) have been booming in recent years. Renewable five-membered γ-butyrolactone (γBL) and derivatives would thus be a desirable feedstock to produce poly(γ-butyrolactone) (PγBL) and different (bio-based) functional polyesters. Their copolymerization with other cyclic monomers could also afford an alternative to tune the properties of the resulting materials.Although γBL was traditionally regarded "non-polymerizable", some progresses were made recently concerning the ROP/ROCP of γBL and derivatives. More importantly, some polyesters could be totally depolymerized back to their monomers by thermal or chemical treatment. This review is specially focused on ROP of γ-lactones and their copolymerization with other cyclic monomers by different catalytic/initiating systems, including Lewis/Brønsted acids, organic bases and alkali metal compounds, organometallic compounds, and cooperative bicomponent catalytic systems. The depolymerization process of some obtained polyesters is also discussed.

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Catalyst‐Sidearm‐Induced Stereoselectivity Switching in Polymerization of a Racemic Lactone for Stereocomplexed Crystalline Polymer with a Circular Life Cycle

Cited by 29 publications

References 52 publications

Stereochemical enhancement of polymer properties

Stereochemical enhancement of polymer properties

High-performance pan-tactic polythioesters with intrinsic crystallinity and chemical recyclability

Ring-opening polymerization of γ-lactones and copolymerization with other cyclic monomers

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