Nickel-Catalyzed Coordination Polymerization-Induced Self-Assembly of Helical Poly(aryl isocyanide)s

Jimaja, Sètuhn; Varlas, Spyridon; Xie, Yujie; Foster, Jeffrey C.; Taton, Daniel; Dove, Andrew P.; O’Reilly, Rachel K.

doi:10.1021/acsmacrolett.9b00972

Cited by 43 publications

(38 citation statements)

References 53 publications

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“…Generally, the catalytic materials used in the polymerization of isonitrile included nickel catalyst [ 22 ], palladium-platinum binary catalyst [ 23 ], and rhodium catalyst [ 24 ]. However, the molecular weight distribution of the polymer obtained by the polymerization of isonitrile is wide when we used nickel as catalyst, and the length of the polymer chain is not easy to control.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Antibacterial, and Antitumor Activity of Linear Polyisocyanide Quaternary Ammonium Salts with Different Structures and Chain Lengths

et al. 2021

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The development of organic polymer materials for disinfection and sterilization is thought of as one of the most promising avenues to solve the growth and spread of harmful microorganisms. Here, a series of linear polyisocyanide quaternary ammonium salts (L-PQASs) with different structures and chain lengths were designed and synthesized by polymerization of phenyl isocyanide monomer containing a 4-chloro-1-butyl side chain followed by quaternary amination salinization. The resultant compounds were characterized by 1H NMR and FT-IR. The antibacterial activity of L-PQASs with different structures and chain lengths against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) was evaluated by determining the minimum inhibitory concentrations (MICs). The L-POcQAS-M50 has the strongest antimicrobial activity with MICs of 27 μg/mL against E. coli and 32 μg/mL against S. aureus. When the L-PQASs had the same polymerization degree, the order of the antibacterial activity of the L-PQASs was L-POcQAS-Mn > L-PBuQAS-Mn > L-PBnQAS-Mn > L-PDBQAS-Mn (linear, polyisocyanide quaternary ammonium salt, monomer, n = 50,100). However, when L-PQASs had the same side chain, the antibacterial activity reduced with the increase of the molecular weight of the main chain. These results demonstrated that the antibacterial activity of L-PQASs was dependent on the structure of the main chain and the length of the side chain. In addition, we also found that the L-POcQAS-M50 had a significant killing effect on MK-28 gastric cancer cells.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Antibacterial, and Antitumor Activity of Linear Polyisocyanide Quaternary Ammonium Salts with Different Structures and Chain Lengths

et al. 2021

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“…To this end, main-chain helical assemblies have been constructed by PISA but the mechanism is distinctly different from that of supramolecular chirality in polymer side chains. In 2020, O’Reilly et al presented a facile and tunable one-pot methodology, termed nickel-catalyzed coordination PISA (NiCCO-PISA) [ 238 ], to construct helical poly(aryl isocyanide)s in situ ( Figure 15 b). Various chiral superstructure morphologies, such as spheres, worms and vesicles, were constructed simultaneously during the process of polymerization.…”

Section: Supramolecular Chirality Of Azo-polymers Constructed By Imentioning

confidence: 99%

“…(Red represents solvophobic segments, and blue represents solvophilic segments). (( a ) Reproduced from [ 109 ] with permission from The Royal Society of Chemistry; ( b ) and ( c ), reprinted with permission from [ 238 , 239 ]; Copyright (2020, 2020) American Chemical Society).…”

Section: Figurementioning

confidence: 99%

Supramolecular Chirality in Azobenzene-Containing Polymer System: Traditional Postpolymerization Self-Assembly Versus In Situ Supramolecular Self-Assembly Strategy

Cheng

Miao

Qian

et al. 2020

IJMS

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Recently, the design of novel supramolecular chiral materials has received a great deal of attention due to rapid developments in the fields of supramolecular chemistry and molecular self-assembly. Supramolecular chirality has been widely introduced to polymers containing photoresponsive azobenzene groups. On the one hand, supramolecular chiral structures of azobenzene-containing polymers (Azo-polymers) can be produced by nonsymmetric arrangement of Azo units through noncovalent interactions. On the other hand, the reversibility of the photoisomerization also allows for the control of the supramolecular organization of the Azo moieties within polymer structures. The construction of supramolecular chirality in Azo-polymeric self-assembled system is highly important for further developments in this field from both academic and practical points of view. The postpolymerization self-assembly strategy is one of the traditional strategies for mainly constructing supramolecular chirality in Azo-polymers. The in situ supramolecular self-assembly mediated by polymerization-induced self-assembly (PISA) is a facile one-pot approach for the construction of well-defined supramolecular chirality during polymerization process. In this review, we focus on a discussion of supramolecular chirality of Azo-polymer systems constructed by traditional postpolymerization self-assembly and PISA-mediated in situ supramolecular self-assembly. Furthermore, we will also summarize the basic concepts, seminal studies, recent trends, and perspectives in the constructions and applications of supramolecular chirality based on Azo-polymers with the hope to advance the development of supramolecular chirality in chemistry.

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“…29 An exception to the described situation is polyisocyanides, which possess a rigid rod-like backbone because they are composed of carbon-carbon single bonds and bear substituents on every backbone atom. [30][31][32] The steric effect of the pendants results in polyisocyanides adopting a rod-like structure, which twists into a helical shape. Recently, we reported a new kind of alkyne-Pd(II) complex that can efficiently catalyze the living polymerization of a diverse range of isocyanide monomers and afforded the synthesis of stereoregular polyisocyanides with predicted M n and very low M w /M n .…”

Section: Introductionmentioning

confidence: 99%

Precise fabrication of porous polymer frameworks using rigid polyisocyanides as building blocks: from structural regulation to efficient iodine capture

Zhou

et al. 2022

Chem. Sci.

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Nickel-Catalyzed Coordination Polymerization-Induced Self-Assembly of Helical Poly(aryl isocyanide)s

Cited by 43 publications

References 53 publications

Design, Synthesis, Antibacterial, and Antitumor Activity of Linear Polyisocyanide Quaternary Ammonium Salts with Different Structures and Chain Lengths

Design, Synthesis, Antibacterial, and Antitumor Activity of Linear Polyisocyanide Quaternary Ammonium Salts with Different Structures and Chain Lengths

Supramolecular Chirality in Azobenzene-Containing Polymer System: Traditional Postpolymerization Self-Assembly Versus In Situ Supramolecular Self-Assembly Strategy

Precise fabrication of porous polymer frameworks using rigid polyisocyanides as building blocks: from structural regulation to efficient iodine capture

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