Aroylacetylene-Based Amino-Yne Click Polymerization toward Nitrogen-Containing Polymers

Chen, Xu; Bai, Tianwen; Hu, Rong; Song, Bo; Lü, Lin; Ling, Jun; Qin, Anjun; Tang, Ben Zhong

doi:10.1021/acs.macromol.9b02747

Cited by 34 publications

(44 citation statements)

References 49 publications

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“…Another recent report described the spontaneous polymerization between aryl ynones and various 1°or 2°diamines 205 and is similar to the substrates employed by Bass and coworkers in their seminal studies. 202 Nevertheless, this work did improve the molecular weight of the resulting polymers (up to 49 kDa) and investigated the polymer stereochemistry where Z-isomeric polymers were obtained when employing 2°amines and E-isomers for 1°amines, in addition to high thermal stabilities (T d s > 300 °C).…”

Section: Trends In Reactivitymentioning

confidence: 61%

Click Nucleophilic Conjugate Additions to Activated Alkynes: Exploring Thiol-yne, Amino-yne, and Hydroxyl-yne Reactions from (Bio)Organic to Polymer Chemistry

et al. 2021

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The 1,4-conjugate addition reaction between activated alkynes or acetylenic Michael acceptors and nucleophiles (i.e., the nucleophilic Michael reaction) is a historically useful organic transformation. Despite its general utility, the efficiency and outcomes can vary widely and are often closely dependent upon specific reaction conditions. Nevertheless, with improvements in reaction design, including catalyst development and an expansion of the substrate scope to feature more electrophilic alkynes, many examples now present with features that are congruent with Click chemistry. Although several nucleophilic species can participate in these conjugate additions, ubiquitous nucleophiles such as thiols, amines, and alcohols are commonly employed and, consequently, among the most well developed. For many years, these conjugate additions were largely relegated to organic chemistry, but in the last few decades their use has expanded into other spheres such as bioorganic chemistry and polymer chemistry. Within these fields, they have been particularly useful for bioconjugation reactions and step-growth polymerizations, respectively, due to their excellent efficiency, orthogonality, and ambient reactivity. The reaction is expected to feature in increasingly divergent application settings as it continues to emerge as a Click reaction.

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Section: Trends In Reactivitymentioning

confidence: 61%

Click Nucleophilic Conjugate Additions to Activated Alkynes: Exploring Thiol-yne, Amino-yne, and Hydroxyl-yne Reactions from (Bio)Organic to Polymer Chemistry

et al. 2021

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“…The exploration of new polymerization reactions for the synthesis of functional polymers with specific structures and excellent properties is fundamental in polymer chemistry and materials science. − Triple-bonded building blocks such as isocyanides, nitriles, and alkynes have been admitted to be significant monomers in synthetic polymer chemistry, owing to their excellent reactivity, adaptable reaction types, simple synthesis, and so forth. − Over the past years, plentiful polymerization reactions based on triple-bond building blocks have been developed. − As an isomer of nitrile, isocyanides have high reactivity and unusual valence structures and are often used as structural units for the synthesis of heteroatom-containing compounds. However, compared with their huge number of organic reactions, the polymerizations based on isocyanides still need to be further explored.…”

Section: Introductionmentioning

confidence: 99%

Multicomponent Polymerization of Alkynes, Isocyanides, and Isocyanates toward Heterocyclic Polymers

Wang

Peng

et al. 2021

Macromolecules

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Multicomponent polymerization (MCP) based on isocyanides, among the tremendous synthetic methodologies, is a powerful tool for the synthesis of functional heterocyclic polymers such as poly(maleimide)s (PMDs), which should be further developed. In this work, an atom-economic and catalyst-free MCP of activated alkynes, diisocyanides, and diisocyanates was fully explored. PMDs with high weight-average molecular weights (M w up to 29,000) were facilely produced in satisfactory yields (up to 85%). The resultant polymers show excellent solubility, high thermal stability, and good film-forming ability, and their thin films possess high refraction indices in a range of 1.614−1.710 at 632.8 nm. Therefore, this work not only supplements the isocyanide-based MCPs but also enriches the family of polymerization reactions based on triple-bond building blocks.

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“…[ 1 ] Multicomponent polymerization (MCP) has become a powerful tool for obtaining multifunctional advanced materials due to its excellent structural diversity, mild reaction conditions, and environmental benefits, and has thus attracted much attention. [ 2–11 ] In recent years, triple‐bond compounds, such as isonitriles [ 12–17 ] and alkynes, [ 18–24 ] have been widely used to prepare novel polymers through MCP. For instance, in 2018, Li et al.…”

Section: Introductionmentioning

confidence: 99%

Catalyst‐Free Multicomponent Cyclopolymerizations of Diisocyanides, Activated Alkynes, and 1,4‐Dibromo‐2,3‐Butanedione: a Facile Strategy toward Functional Polyiminofurans Containing Bromomethyl Groups

Zhu

Han

et al. 2020

Macromol. Rapid Commun.

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Polymers containing iminofuran (PIFs) are rarely reported due to the lack of simple and effective synthesis methods. In this work, a novel multicomponent cyclopolymerization (MCCP) of diisocyanides, activated alkynes, and 1,4‐dibromo‐2,3‐butanedione using catalyst‐free one‐pot reactions under mild conditions to prepare PIFs containing bromomethyl groups is reported. PIFs with good solubility and thermal stability are obtained with high Mws (up to 19 600) and good yields (up to 89.5%) under optimized polymerization conditions. The structure of the PIFs is characterized by nuclear magnetic resonance, Fourier transform infrared spectroscopy, and gel permeation chromatography. The photophysical properties indicate that polymers P1a2b3 and P1c2b3 have cluster‐triggered emission characteristics. Thin films made from PIFs quickly degrade under UV irradiation. Moreover, the obtained polymers are decorated with bromomethyl and carboxylate groups in the side chain, which can be postfunctionalized to prepare multifunctional materials, such as star branched polymers and biomedical carrier materials. Thus, this work not only enriches the field of polymerization based on isocyanates and activated alkynes but also provides a facile strategy toward functional iminofuran polymers.

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Aroylacetylene-Based Amino-Yne Click Polymerization toward Nitrogen-Containing Polymers

Cited by 34 publications

References 49 publications

Click Nucleophilic Conjugate Additions to Activated Alkynes: Exploring Thiol-yne, Amino-yne, and Hydroxyl-yne Reactions from (Bio)Organic to Polymer Chemistry

Click Nucleophilic Conjugate Additions to Activated Alkynes: Exploring Thiol-yne, Amino-yne, and Hydroxyl-yne Reactions from (Bio)Organic to Polymer Chemistry

Multicomponent Polymerization of Alkynes, Isocyanides, and Isocyanates toward Heterocyclic Polymers

Catalyst‐Free Multicomponent Cyclopolymerizations of Diisocyanides, Activated Alkynes, and 1,4‐Dibromo‐2,3‐Butanedione: a Facile Strategy toward Functional Polyiminofurans Containing Bromomethyl Groups

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