Using carbon dioxide and its sulfur analogues as monomers in polymer synthesis

Luo, Ming; Li, Yang; Zhang, Yingying; Zhang, Xinghong

doi:10.1016/j.polymer.2015.11.011

Cited by 98 publications

(72 citation statements)

References 240 publications

(326 reference statements)

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“…Since, carbonyl sulfide (COS) is a structural analogue of CO 2 (and CS 2 ), scientist were strongly motivated to convert COS into polymers, in a way similar with the CO 2 –epoxide copolymerization, producing poly(thiocarbonate) directly from the selective and completely alternating copolymerization of COS with epoxides via metal catalysis (Scheme D) . A recent report focused on the catalytic synthesis of poly(trimethylenethiocarbonate), a sulfur‐containing crystalline copolymer, from the completely alternating copolymerization of COS with oxetane (OX) .…”

Section: Chemistrymentioning

confidence: 99%

Sulfur Chemistry in Polymer and Materials Science

Mutlu

Ceper

et al. 2018

Macromol. Rapid Commun.

256

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The ORCID identification number(s) for the author(s) of this article can be found under https://doi.org/10.1002/marc.201800650. ChemistryBefore moving to the recent advances within the last 5 years in the diverse applications of sulfur chemistry in polymer and Sulfur-Containing PolymersSulfur and its functional groups are major players in an area of exciting research taking place in modern polymer and materials science, both in academia and industry. In fact, manifold sulfur-based reactions that are both exceptionally versatile as well as tremendously useful have been implemented, and further utilized for the design and preparation of polymeric materials that lead to a plethora of applications ranging from medicine to optics and nanotechnology to separation science. Hence, within this review, an overview of strategies and developments used over the last 5 years to reinforce the importance of the sulfur functional group in modern polymer and materials science is presented. In particular, many important references in the primary literature of sulfur chemistry are referred to, including thiol-ene, thiol-yne, thiol-Michael addition, disulfide cross-linking, and thiol-disulfide exchange, among others, by explaining and illustrating the important principles. Last but not least, the grand aim to underpin the importance of sulfur in modern polymer and materials science is achieved by presenting selected examples in diverse fields and postulating the respective potential for real-world applications. he is now a full professor at KIT.sulfur atoms, and tetraphenylethene-bearing di(alkyl bromide) (Scheme 3). The yield of the polymerization was dependent on the di(alkyl bromide) monomer; the longer spacer between the aromatic moiety and the reactive bromide end groups Scheme 1. The discussion henceforth focuses on the synthesis of polymers possessing the depicted sulfur functional groups. Scheme 2.Representative examples of polythioethers prepared via A) the nucleophilic substitution reaction between an electrophilic dihalide with nucleophilic derivatives of dithiols under alkaline conditions; B) the thiol-ene/yne addition reaction between AA and BB type monomers (i.e., dithiols and dienes/diynes); and C) radical or ionic ring-opening of sulfurcontaining strained rings.Scheme 3. The thiol-bromo polymerization of conformationally fixed monomers to provide multifunctional polymers. [19] Macromol. Rapid Commun. 2019, 40, 1800650 Scheme 4. The regioselective selective nucleophilic aromatic substitution between thiol and fluorinated aromatic compounds, the para-fluorothiol reaction (PFTR).Scheme 5. Synthesis of a linear polymer via PFTR-reaction. [21]

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Section: Chemistrymentioning

confidence: 99%

Sulfur Chemistry in Polymer and Materials Science

Mutlu

Ceper

et al. 2018

Macromol. Rapid Commun.

256

220

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“…24,25 Since this pioneering work many catalysts have been developed for the copolymerization of CO 2 with epoxides. [13][14][15][16][17][18] Especially zinc based catalyst systems were shown to be efficient. A variety of initiating systems based on different zinc species alone 26,27 as well as in combination with additives e.g.…”

Section: -23mentioning

confidence: 99%

Copolymerization of CO₂ and epoxides mediated by zinc organyls

2018

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Herein we report the copolymerization of CHO with CO 2 in the presence of various zinc compounds R 2 Zn (R ¼ Et, Bu, iPr, Cy and Ph). Several zinc organyls proved to be efficient catalysts for this reaction in the absence of water and co-catalyst. Notably, readily available Bu 2 Zn reached a TON up to 269 and an initial TOF up to 91 h À1 . The effect of various parameters on the reaction outcome has been investigated. Poly(ether)carbonates with molecular weights up to 79.3 kg mol À1 and a CO 2 content of up to 97% were obtained. Under standard reaction conditions (100 C, 2.0 MPa, 16 h) the influence of commonly employed co-catalysts such as PPNCl and TBAB has been investigated in the presence of Et 2 Zn (0.5 mol%). The reaction of other epoxides (e.g. propylene and styrene oxide) under these conditions led to no significant conversion or to the formation of the respective cyclic carbonate as the main product.

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“…in 1969, various catalytic systems were developed to improve the reaction efficiency . Double metal cyanide (DMC) catalyst is an attractive heterogeneous system for its high stability, high reactivity and moisture tolerance . In recent decades, the catalytic performance of DMC catalysts has been improved by altering the metal salts and complexing agent, using mechanochemistry method, preparing composite or hybrid catalysts[5e, 9c, 10] and so on.…”

Section: Introductionmentioning

confidence: 99%

Effects of addition mode on Zn–Co double metal cyanide catalyst for synthesis of oligo(propylene‐carbonate) diols

Ning

et al. 2018

Applied Organom Chemis

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Zn-Co double metal cyanide (DMC) complexes are promising catalytic systems for copolymerization of epoxide and CO 2 . In the work reported, Zn-Co DMC catalysts were prepared by parallel-flow dropping, forward dropping and reverse dropping methods, aiming to provide an insight into the effect of addition mode on catalyst structure and catalytic performance. Catalytic properties were evaluated using the copolymerization reaction of propylene oxide (PO) and CO 2 in the presence of chain transfer agent. The results indicated that the factors that affect crystalline state are different for different modes. And excess zinc chloride is the prerequisite for organic ligands to be retained in the catalyst and affect the structure. In addition, a catalyst with flower-like morphology was obtained with the parallel-flow dropping method which provided larger surface area. An appropriate O/Zn value ensured abundant active PO which would suppress the backbiting process by forming consecutive PO units adjacent to CO 2 units. Oligo(propylene-carbonate) diols with average molecular weight of 1020 g mol −1 , CO 2 incorporation of 24.92% and W PC of 5.14 wt% were obtained at 80°C and 2 MPa.

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Using carbon dioxide and its sulfur analogues as monomers in polymer synthesis

Cited by 98 publications

References 240 publications

Sulfur Chemistry in Polymer and Materials Science

Sulfur Chemistry in Polymer and Materials Science

Copolymerization of CO₂ and epoxides mediated by zinc organyls

Effects of addition mode on Zn–Co double metal cyanide catalyst for synthesis of oligo(propylene‐carbonate) diols

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Using carbon dioxide and its sulfur analogues as monomers in polymer synthesis

Cited by 98 publications

References 240 publications

Sulfur Chemistry in Polymer and Materials Science

Sulfur Chemistry in Polymer and Materials Science

Copolymerization of CO2 and epoxides mediated by zinc organyls

Effects of addition mode on Zn–Co double metal cyanide catalyst for synthesis of oligo(propylene‐carbonate) diols

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Copolymerization of CO₂ and epoxides mediated by zinc organyls