Synthesis and characterization of guanidinate tin(<scp>ii</scp>) complexes for ring-opening polymerization of cyclic esters

Ungpittagul, Thasanaporn; Wongmahasirikun, Phonpimon; Phomphrai, Khamphee

doi:10.1039/d0dt01115k

Cited by 16 publications

(11 citation statements)

References 87 publications

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“…41,44 In particular, the recent use of metal catalysts with NHC ligands has led to incredibly fast, controlled polymerizations, which is another advantage considering the lengthy reaction times involved in ring closure approaches. 45,46 While rapid progress has been made in the synthesis of cyclic polymers over the past decade, some synthetic questions remain. For instance, the possibility of catenanes being produced in these polymerizations has yet to be discussed in depth to our knowledge.…”

Section: ■ Scope Of Reviewmentioning

confidence: 99%

“…While REPs do not consistently give low Đ values, they do allow for easier access to high-molecular-weight cyclic polymers and would be more appropriate for industrial-scale cyclic polymerizations due to the absence of dilute conditions and the single step nature of the REP. This approach has been developed substantially over the past decade, and an array of options are now available which provide controlled ( Đ < 1.5) cyclic polymers. , In particular, the recent use of metal catalysts with NHC ligands has led to incredibly fast, controlled polymerizations, which is another advantage considering the lengthy reaction times involved in ring closure approaches. , …”

Section: General Synthetic Approaches: Ring Closure and Ring Expansionmentioning

confidence: 99%

“…Due to the distinctly Scheme 2. NHC-Like Tin(II) Complexes for Use in REP of Lactide and ε-Caprolactone by Ungpittagul et al46 …”

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confidence: 99%

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Synthesis, Properties, and Applications of Bio-Based Cyclic Aliphatic Polyesters

et al. 2021

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Cyclic polymers have long been reported in the literature, but their development has often been stunted by synthetic difficulties such as the presence of linear contaminants. Research into the synthesis of these polymers has made great progress in the past decade, and this review covers the synthesis, properties, and applications of cyclic polymers, with an emphasis on bio-based aliphatic polyesters. Synthetic routes to cyclic polymers synthesized from bioderived monomers, alongside mechanistic descriptions for both ring closure and ring expansion polymerization approaches, are reviewed. The review also highlights some of the unique physical properties of cyclic polymers together with potential applications. The findings illustrate the substantial recent developments made in the syntheses of cyclic polymers, as well as the progress which can be made in the commercialization of bio-based polymers through the versatility this topology provides.

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Section: ■ Scope Of Reviewmentioning

confidence: 99%

Section: General Synthetic Approaches: Ring Closure and Ring Expansionmentioning

confidence: 99%

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Synthesis, Properties, and Applications of Bio-Based Cyclic Aliphatic Polyesters

et al. 2021

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“…Atactic cyclic PLA was synthesized using a tin(II) catecholate system generated in situ by the reaction of tin octoate and a catechol. Comparable linear polymers (of rac - and l -lactide) were made by replacing the coinitiator with benzyl alcohol, a common coinitiator for linear polymerizations of lactide . This method was used for the majority of samples used in this study.…”

Section: Methodsmentioning

confidence: 99%

Comparison of Cyclic and Linear Poly(lactide)s Using Small-Angle Neutron Scattering

Yang¹,

Davidson²,

Edler

et al. 2022

Macromolecules

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Small-angle neutron scattering (SANS) experiments were conducted on cyclic and linear polymers of racemic and l-lactides (PLA) with the goal of comparing chain configurations, scaling, and effective polymer–solvent interactions of the two topologies in acetone-d 6 and THF-d 8. There are limited reports of SANS results on cyclic polymers due to the lack of substantial development in the field until recently. Now that pure, well-defined cyclic polymers are accessible, unanswered questions about their rheology and physical conformations can be better investigated. Previously reported SANS experiments have used cyclic and linear polystyrene samples; therefore, our work allowed for direct comparison using a contrasting (structurally and sterically) polymer. We compared SANS results of cyclic and linear PLA samples with various microstructures and molecular weights at two different temperatures, allowing for comparison with a wide range of variables. The results followed the trends of previous experiments, but much greater differences in the effective polymer–solvent interaction parameters between cyclic and linear forms of PLA were observed, implying that the small form factor and hydrogen bonding in PLA allowed for much more compact conformations in the cyclic form only. Also, the polymer microstructure was found to influence polymer–solvent interaction parameters substantially. These results illustrate how the difference in polymer–solvent interactions between cyclic and linear polymers can vary greatly depending on the polymer in question and the potential of neutron scattering as a tool for identification and characterization of the cyclic topology.

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“…Traditional chemical catalysts in the synthesis of polyesters have led to the production of valuable commercial products. However, in this case, polymerization usually takes place at high temperatures (150–280 °C) using complex organic catalysts [ 161 , 162 , 163 , 164 ] or catalysts containing metal ions, including heavy metals [ 165 , 166 ]. Chemical synthesis at high temperatures is often accompanied by side processes, with a significant limitation in this case being the difficulty in dealing with thermally or chemically unstable monomers.…”

Section: Enzymes and Polymers Produced With Themmentioning

confidence: 99%

Prospects of Using Biocatalysis for the Synthesis and Modification of Polymers

Nikulin

Švedas

2021

Molecules

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Trends in the dynamically developing application of biocatalysis for the synthesis and modification of polymers over the past 5 years are considered, with an emphasis on the production of biodegradable, biocompatible and functional polymeric materials oriented to medical applications. The possibilities of using enzymes not only as catalysts for polymerization but also for the preparation of monomers for polymerization or oligomers for block copolymerization are considered. Special attention is paid to the prospects and existing limitations of biocatalytic production of new synthetic biopolymers based on natural compounds and monomers from biomass, which can lead to a huge variety of functional biomaterials. The existing experience and perspectives for the integration of bio- and chemocatalysis in this area are discussed.

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Synthesis and characterization of guanidinate tin(ii) complexes for ring-opening polymerization of cyclic esters

Abstract: Tin(ii) complexes suported by guanidinate ligands have been synthesized and shown to polymerize lactide and ε-caprolactone to cyclic polyesters.

Cited by 16 publications

References 87 publications

Synthesis, Properties, and Applications of Bio-Based Cyclic Aliphatic Polyesters

Synthesis, Properties, and Applications of Bio-Based Cyclic Aliphatic Polyesters

Comparison of Cyclic and Linear Poly(lactide)s Using Small-Angle Neutron Scattering

Prospects of Using Biocatalysis for the Synthesis and Modification of Polymers

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