New Routes to Tailor‐Made Polyesters

Fukushima, Kazuki; Fujiwara, Tomoko

doi:10.1002/9781118967904.ch6

Cited by 5 publications

(7 citation statements)

References 188 publications

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“…M n and D̵ M were calibrated with polystyrene (PS) standards (ranging from 580 to 2.2 × 10 6 g/mol). Synthetic Procedures for PMDO (5). Synthesis of MDO (4).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…In the research phase, numerous functional polymers have been tested for applications in drug-delivery systems and in scaffold materials for tissue regeneration. Biocompatibility is essential and a primary concern in designing these medical polymers. , For tissue engineering approaches, biodegradability is also important, and thus biodegradable polymers, such as aliphatic polyesters and polycarbonates, have been employed as biomedical materials. , …”

Section: Introductionmentioning

confidence: 99%

“…2,3 For tissue engineering approaches, biodegradability is also important, and thus biodegradable polymers, such as aliphatic polyesters and polycarbonates, have been employed as biomedical materials. 4,5 Bioabsorbable stents and artificial blood vessels composed of biodegradable polymers are ideal treatment devices for vascular diseases. 6,7 However, the challenge associated with the current polymeric devices is their blood compatibility, which is one of the high-ranked biocompatibilities.…”

Section: ■ Introductionmentioning

confidence: 99%

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Methoxy-Functionalized Glycerol-Based Aliphatic Polycarbonate: Organocatalytic Synthesis, Blood Compatibility, and Hydrolytic Property

Montagna

Takahashi

Tsai

et al. 2021

ACS Biomater. Sci. Eng.

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Polymers that are biocompatible and degradable are desired for tissue engineering approaches in the treatment of vascular diseases, especially for those involving small-diameter blood vessels. Herein, we report the compatibility of a newly developed glycerol-based aliphatic polycarbonate possessing simple methoxy side groups, named poly(5-methoxy-1,3-dioxan-2one) (PMDO), with blood cells and plasma proteins as well as its susceptibility to hydrolysis. As a consequence of the organocatalytic ringopening polymerization (ROP) of a methoxy-functionalized cyclic carbonate derived from glycerol, PMDO with a sufficiently high molecular weight (M n 14 kg/mol) and a narrow distribution (D̵ M 1.12) was obtained for evaluation as a bulk biomaterial. This study demonstrates for the first time the organocatalytic ROP of a glycerol-based cyclic carbonate in a controlled manner. Compared with the clinically applied aliphatic polycarbonate poly(trimethylene carbonate) (PTMC), PMDO inhibits platelet adhesion by 33% and denaturation of fibrinogen by 23%. Although the wettability of PMDO based on water contact angle was almost comparable to those of PTMC and poly(ethylene terephthalate), the reason for the inhibited platelet adhesion and protein denaturation appeared to be related to the presence of specific hydrated water formed in the hydrated polymer. The improved hydration of PMDO also enhanced the susceptibility to hydrolysis, with PMDO demonstrating a slightly higher hydrolytic property than PTMC. This simple glycerol-based aliphatic polycarbonate has the following benefits: bio-based characteristics of glycerol and improved blood compatibility and hydrolytic biodegradability stemming from moderate hydration of the methoxy side groups.

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“…M n and D̵ M were calibrated with polystyrene (PS) standards (ranging from 580 to 2.2 × 10 6 g/mol). Synthetic Procedures for PMDO (5). Synthesis of MDO (4).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Methoxy-Functionalized Glycerol-Based Aliphatic Polycarbonate: Organocatalytic Synthesis, Blood Compatibility, and Hydrolytic Property

Montagna

Takahashi

Tsai

et al. 2021

ACS Biomater. Sci. Eng.

Self Cite

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“…They are both commonly encountered in step-growth polymerizations. [59][60][61][62][63][64] PTSA does not present any signicant toxicity. 65 Ti(OBu) 4 is commonly considered as less toxic than conventional transesterication antimony catalysts.…”

Section: Polycondensation Of Ab Monomersmentioning

confidence: 83%

Complete depolymerization of poly(ester-alt-thioether)s under mild conditions into AB functional monomers

Le Luyer,

Guégan,

Illy

2024

RSC Sustain.

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“…Specifically, green chemistry plays an increasingly crucial role in polyester synthesis by virtue of the abundance of the relevant renewable resources [ 124 ] and wide application of green solvents. Meanwhile, synthesis of tailor-made polyesters can be conducted in a mild, selective and even atom-economic manner using new synthetic routes [ 125 ]. Furthermore, new chemical findings featuring high tolerance to polar groups renders straightforward the synthesis of functional polyesters [ 126 ].…”

Section: Discussionmentioning

confidence: 99%

Precision Aliphatic Polyesters via Segmer Assembly Polymerization

Zeng

Yang

2018

Molecules

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Precise structure-property relation of a biodegradable polymer (e.g., aliphatic polyester) is anticipated only if monomer units and chiral centers are arranged in a defined primary sequence as a biomacromolecule. An emerging synthetic methodology, namely segmer assembly polymerization (SAP), is introduced in this paper to reveal the latest progress in polyester synthesis. Almost any periodic polyester envisioned can be synthesized via SAP using a programed linear or cyclic monomer. In this context, the macroscopic properties of a biodegradable polymer are fundamentally determined by microstructural information through a bottom-up approach. It can be highlighted that SAP ideally combines the precision of organic synthesis and the high efficiency of a polymerization reaction. Previously reported strategies including nucleophilic displacement, polyesterification, cross-metathesis polymerization (CMP), ring-opening polymerization (ROP), ring-opening metathesis polymerization (ROMP) and entropy-driven ring-opening metathesis polymerization (ED-ROMP) are critically reviewed in this paper to shed light on precision synthesis of aliphatic polyesters via SAP. Emerging yet challenging, SAP is a paradigm which reflects the convergence of organic and polymer chemistries and is also an efficient pathway to microstructural control. The current status, future challenges and promising trends in this realm are analyzed and discussed in this overview of the state-of-the-art.

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New Routes to Tailor‐Made Polyesters

Cited by 5 publications

References 188 publications

Methoxy-Functionalized Glycerol-Based Aliphatic Polycarbonate: Organocatalytic Synthesis, Blood Compatibility, and Hydrolytic Property

Methoxy-Functionalized Glycerol-Based Aliphatic Polycarbonate: Organocatalytic Synthesis, Blood Compatibility, and Hydrolytic Property

Complete depolymerization of poly(ester-alt-thioether)s under mild conditions into AB functional monomers

Precision Aliphatic Polyesters via Segmer Assembly Polymerization

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