Atom-economical, room-temperature, and high-efficiency synthesis of polyamides <i>via</i> a three-component polymerization involving benzoxazines, odorless isocyanides, and water

Zhang, Jie; Shi, Wei; Li, Qiao; Chen, Tinglu; Zhou, Xinyu; Yang, Chang Ying; Zhang, Kesong; Xie, Zhenzhen

doi:10.1039/c8py01256c

Cited by 32 publications

(14 citation statements)

References 42 publications

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“…Brønsted acids, especially p -toluenesulfonic acid (TsOH) [ 255 , 269 , 289 , 290 , 291 ] are widely reported to accelerate oxazine ring-opening by the protonation of nitrogen and/or oxygen atoms followed by a transformation into the final reaction products. The percentage of N,O -acetal (unit A) and Mannich bridge (unit B) structures in polybenzoxazine are affected by TsOH mediated polymerization of p C-a [ 269 ].…”

Section: Acceleration Of the Rate Of Polymerization Via Intermolecular Interactionmentioning

confidence: 99%

Review on the Accelerated and Low-Temperature Polymerization of Benzoxazine Resins: Addition Polymerizable Sustainable Polymers

et al. 2021

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Due to their outstanding and versatile properties, polybenzoxazines have quickly occupied a great niche of applications. Developing the ability to polymerize benzoxazine resin at lower temperatures than the current capability is essential in taking advantage of these exceptional properties and remains to be most challenging subject in the field. The current review is classified into several parts to achieve this goal. In this review, fundamentals on the synthesis and evolution of structure, which led to classification of PBz in different generations, are discussed. Classifications of PBzs are defined depending on building block as well as how structure is evolved and property obtained. Progress on the utility of biobased feedstocks from various bio-/waste-mass is also discussed and compared, wherever possible. The second part of review discusses the probable polymerization mechanism proposed for the ring-opening reactions. This is complementary to the third section, where the effect of catalysts/initiators has on triggering polymerization at low temperature is discussed extensively. The role of additional functionalities in influencing the temperature of polymerization is also discussed. There has been a shift in paradigm beyond the lowering of ring-opening polymerization (ROP) temperature and other areas of interest, such as adaptation of molecular functionality with simultaneous improvement of properties.

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Section: Acceleration Of the Rate Of Polymerization Via Intermolecular Interactionmentioning

confidence: 99%

Review on the Accelerated and Low-Temperature Polymerization of Benzoxazine Resins: Addition Polymerizable Sustainable Polymers

et al. 2021

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“…Shi and co‐workers developed a high‐efficiency, octylphosphonic acid‐catalyzed three‐component reaction of benzoxazines, isocyanides, and water toward phenolic hydroxyl amides ( Scheme A). [ 46 ] Afterward, they developed this MCR to an efficient MCP, and polyimides with satisfactory molecular weights ( M w up to 21 000) were produced in moderate yields (up to 75%) (Scheme 4B). Moreover, tris(4‐isocyanophenyl)amine was employed to construct hyperbranched polymers by controlling the ratio of diisocyanides to prevent the occurrence of crosslinking.…”

Section: Mcps With Water As a Comonomermentioning

confidence: 99%

Multicomponent Polymerizations Involving Green Monomers

Wang

Qin

Tang

2020

Macromol. Rapid Commun.

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Green monomers, such as oxygen (O2), water (H2O), and carbon dioxide (CO2), refer to a kind of natural reagents with abundant, nontoxic, cheap, environmentally friendly, renewable, and sustainable features. These monomers have been used in multicomponent polymerizations (MCPs) toward functional polymers. In this review, the recent development of MCPs involving green monomers of O2‐, H2O‐, and CO2 is summarized. The catalytic systems, polymerization conditions, the molecular weights, and potential applications of resultant polymers are briefly discussed. Furthermore, the existing challenges and the promising opportunities are concisely provided.

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“…The preparation of optoelectronic polymers with conjugated structures from MCPs remains quite challenging due to the limited solubility of conjugated polymers, possible defects from the products, and narrow range of applicable monomers . The reported MCPs generally produce non‐conjugated products such as polyamides, polyamines, and poly(ester‐amide)s . To explore the general applicability of MCPs and their polymerization product structures, a popular tandem strategy in organic synthesis has been introduced to MCPs .…”

Section: Background and Originality Contentmentioning

confidence: 99%

Multicomponent Tandem Polymerization of Aromatic Alkynes, Carbonyl Chloride, and Fischer's Base toward Poly(diene merocyanine)s

Tang

Zhang

et al. 2019

Chin. J. Chem.

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Summary of main observation and conclusion Multicomponent polymerization (MCP) is a popular tool to construct polymers with diverse structure, simple operation, and high efficiency, which faces the challenges of limited product structures. Multicomponent tandem polymerization (MCTP), combining two or multiple reactions in a one‐pot fashion, could expand the scope of MCP and enrich the polymer structures. Herein, a one‐pot three‐component tandem polymerization of diynes, carbonyl chloride, and Fischer's base has been developed to afford conjugated poly(diene merocyanine)s with mild condition, satisfactory molecular weights (Mw up to 10900 g/mol) and yields (up to 81%). The polymers enjoy good solubility and high thermal stability. The unique emission behavior of the model compound and polymer show that they are aggregation‐induced emission (AIE)‐active, suggesting that the diene merocyanine moiety is a potential AIEgen. This MCTP shows great potential in the preparation of functional polymer materials, which could build new AIE functional units directly from the polymerization, demonstrating its synthetic simplicity and elegance.

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Atom-economical, room-temperature, and high-efficiency synthesis of polyamides via a three-component polymerization involving benzoxazines, odorless isocyanides, and water

Abstract: High-efficiency three-component polymerization involving benzoxazines, odorless isocyanides, and water to synthesize polyamide derivatives at room temperature was reported here.

Cited by 32 publications

References 42 publications

Review on the Accelerated and Low-Temperature Polymerization of Benzoxazine Resins: Addition Polymerizable Sustainable Polymers

Review on the Accelerated and Low-Temperature Polymerization of Benzoxazine Resins: Addition Polymerizable Sustainable Polymers

Multicomponent Polymerizations Involving Green Monomers

Multicomponent Tandem Polymerization of Aromatic Alkynes, Carbonyl Chloride, and Fischer's Base toward Poly(diene merocyanine)s

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