Stereocontrolled ring-opening polymerization of cyclic esters: synthesis of new polyester microstructures

Thomas, Christophe M.

doi:10.1039/b810065a

Cited by 782 publications

(422 citation statements)

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“…1 Over the past two decades, ring-opening polymerization catalysts have been used to produce aliphatic polyesters with excellent structural control. 2 Advances in (stereo)control afford polymers with precise organization, 3 and the development of living catalysts has provided the opportunity to synthesize polyesters of defined molecular weight and sequence. 4 In order to further extend the applications of these polymers, it is necessary to vary and finely tune their physico-chemical properties.…”

Section: Introductionmentioning

confidence: 99%

Facile and efficient chemical functionalization of aliphatic polyesters by cross metathesis

et al. 2016

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International audienceAn effective preparation of new tailor-made macromolecular materials via a combination of two (atom-efficient) catalytic transformations is reported. First, new aliphatic polyesters with alternated composition have been prepared using a salen aluminum catalyst system. Next, the pendant vinyl moieties in those copolymers have been selectively transformed into various functional groups by metathesis in the presence of homogeneous Grubbs catalysts. The latter metathesis reaction has been optimized in terms of catalytic activity and selectivity, to define the conditions for an effective and safe procedure that does not affect the macromolecular architecture. All polymer materials have been analyzed by H-1, and C-13 NMR spectroscopy, to diagnose the catalyst selectivities in the copolymerization and metathesis processes

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Section: Introductionmentioning

confidence: 99%

Facile and efficient chemical functionalization of aliphatic polyesters by cross metathesis

et al. 2016

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“…PLA has attracted much attention from researchers in both industry and academia. The most efficient method for the synthesis of PLA is ring-opening polymerization (ROP) of the six-membered cyclic ester lactide with a variety of metal-based complexes [4,[9][10][11]. Organocatalysts also have been employed to more precisely control the synthesis of ring-opening polymerization [12].…”

Section: Introductionmentioning

confidence: 99%

Computational Studies on the Selective Polymerization of Lactide Catalyzed by Bifunctional Yttrium NHC Catalyst

et al. 2017

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Abstract:A theoretical investigation of the ring-opening polymerization (ROP) mechanism of rac-lactide (LA) with an yttrium complex featuring a N-heterocyclic carbine (NHC) tethered moiety is reported. It was found that the carbonyl of lactide is attacked by N(SiMe 3 ) 2 group rather than NHC species at the chain initiation step. The polymerization selectivity was further investigated via two consecutive insertions of lactide monomer molecules. The insertion of the second monomer in different assembly modes indicated that the steric interactions between the last enchained monomer unit and the incoming monomer together with the repulsion between the incoming monomer and the ligand framework are the primary factors determining the stereoselectivity. The interaction energy between the monomer and the metal center could also play an important role in the stereocontrol.

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“…Among these complexes, aluminum complexes are proving more popular due to the facile nature of the preparation and relatively high degree of stereoregularity in the ROP of lactide. [62,63] Gibson investigated the polymerization rac-lactide by aluminum initiators supported by tetradentate aminophenoxide ligands ( Figure 5) and found that the polymerizations was well-controlled and living, the resultant PLA materials ranged from highly isotactic to highly heterotactic which depending upon the ligand substitution pattern. The system of the unsubstituted phenoxide groups' catalysts (complexes 7 in Figure 5) afforded PLA with high levels of 79% isoselectivity.…”

Section: Nnoo Ligandmentioning

confidence: 99%

Review – recent development of ring-opening polymerization of cyclic esters using aluminum complexes

Ruan

Xiao

et al. 2013

Designed Monomers and Polymers

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With the development of the technology of ring-opening polymerization (ROP) rapidly, many novel aluminum complexes have been designed, synthesized, and applied in initiating ROP of cyclic esters and new stereoregular polymerization mechanism of lactide polymerization have been reported. In this review, the mechanism for ROP of cyclic ester, synthesis of aluminum complexes containing tetradendete ligand, tridentate ligand, bidentate ligand, and bimetallic complexes containing aluminum were reviewed. We hope to give some helpful information for designing aluminum complexes, improving activity, and stereoregularity of aluminum complexes.Keywords: ring-opening polymerization; cyclic ester; aluminum complexes; stereoregularity IntroductionAliphatic polyester is biodegradable and biocompatible materials, which prepared using ring-opening polymerization (ROP) of cyclic ester such as lactide, caprolactone. trimethylene carbonate, and other cyclic ester. [1,2] Due to effective influences of microstructure, molecular weight, and polydispersity indexes (PDIs) on polyester physicochemical properties, the controlled/living ROP for synthesis of polyester which enables the ready to control these parameters attracted an extraordinary amount of research recently.[3-6] During the last two decades, the improvement in catalyst makes it possible to design and synthesis of polyester. [7][8][9][10]

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Stereocontrolled ring-opening polymerization of cyclic esters: synthesis of new polyester microstructures

Cited by 782 publications

References 51 publications

Facile and efficient chemical functionalization of aliphatic polyesters by cross metathesis

Facile and efficient chemical functionalization of aliphatic polyesters by cross metathesis

Computational Studies on the Selective Polymerization of Lactide Catalyzed by Bifunctional Yttrium NHC Catalyst

Review – recent development of ring-opening polymerization of cyclic esters using aluminum complexes

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