A new soft-matter material with old chemistry: Passerini multicomponent polymerization-induced assembly of AIE-active double-helical polymers with rapid visible-light degradability

Liu, Jupen; Luo, Zhonglong; Yu, Le; Zhang, Ping; Wei, Hongqiu; Yu, You

doi:10.1039/d0sc02729d

Cited by 24 publications

(17 citation statements)

References 40 publications

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“…[ 1,2 ] Compared with classic polymerization approaches, MCPs enjoy great structural diversity of products, strong designability of reaction procedure and product structure, mild reaction condition, simple monomer structures, environmental benefits, and so on. [ 3–6 ] Besides the most widely explored isocyanide‐based MCPs including Passerini three‐component polymerization (3CP) of isocyanide, carboxylic acid and oxo‐component (ketone or aldehyde), [ 7–10 ] and Ugi four‐component polymerization (4CP) of isocyanide, carboxylic acid, oxo‐component (ketone or aldehyde) and amine, [ 11–13 ] alkyne‐based MCPs were extensively reported in the past few years, [ 14–16 ] owing to the rich chemistry of alkynes and the unsaturated product structures with potential optoelectronic properties from alkyne chemistry, [ 17 ] which could be applied in optoelectronic devices, [ 18,19 ] or as luminescent materials, [ 14,20 ] and antibacterial materials. [ 21 ]…”

Section: Figurementioning

confidence: 99%

Catalyst‐Free Four‐Component Polymerization of Propiolic Acids, Benzylamines, Organoboronic Acids, and Formaldehyde toward Functional Poly(propargylamine)s

et al. 2020

Macromol. Rapid Commun.

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Multicomponent polymerizations (MCPs) are a group of fascinating polymer synthesis approaches that are developed rapidly in the recent decade. As a popular alkyne‐based MCP, the A3‐polycouplings of alkynes, aldehydes, and amines are developed for the synthesis of poly(propargylamine)s under the catalysis of metal catalysts. In this work, through the design of carboxylic acid group‐activated alkyne monomers, a catalyst‐free, four‐component polymerization of propiolic acids, benzylamines, organoboronic acids, and formaldehyde is reported under mild condition at 45 °C in dichloroethane. This four‐component polymerization is applicable to different monomer structures, which can afford seven poly(propargylamine)s with up to 94% yields and molecular weights of up to 13 900 g mol−1. Moreover, the poly(propargylamine)s demonstrate good solubility and processibility, high thermal stability and light refractivity, unique photophysical property, and so on. The simple monomers, mild condition, low cost, high efficiency, and procedure simplicity of this catalyst‐free four‐component polymerization demonstrates an elegant example of functional polymer synthesis.

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Section: Figurementioning

confidence: 99%

Catalyst‐Free Four‐Component Polymerization of Propiolic Acids, Benzylamines, Organoboronic Acids, and Formaldehyde toward Functional Poly(propargylamine)s

et al. 2020

Macromol. Rapid Commun.

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“…In 2020, Yu and co-workers successfully synthesized a photoresponsive, water-soluble, AIE-active, double-helical polymer via Passerini multicomponent polymerization-induced assembly (Figure 1D). 63 This special photoresponsive polymer exhibits the AIE propriety via through-space interactions of pyridines. When the polymer was irradiated by visible light (452 nm), it degraded into small segments due to the cleavage of the contained photolabile α-acyloxyamide structure via a typical photoinduced electron-transfer process.…”

Section: Construction Of Photoresponsive Aie Polymersmentioning

confidence: 99%

“…Copyright 2019 Elsevier Ltd. (D) In situ generation of 4 from AIE/photoresponsive-inactive monomers by Passerini multicomponent polymerization-induced assembly. Adapted with permission from ref . Copyright 2020 Royal Society of Chemistry.…”

Section: Construction Of Photoresponsive Aie Polymersmentioning

confidence: 99%

“…Observably restricted, the intramolecular vibrational or torsional motions of azobenzene groups upon aggregation lead to a strong AIE effect. In 2020, Yu and co-workers successfully synthesized a photoresponsive, water-soluble, AIE-active, double-helical polymer via Passerini multicomponent polymerization-induced assembly (Figure D) . This special photoresponsive polymer exhibits the AIE propriety via through-space interactions of pyridines.…”

Section: Construction Of Photoresponsive Aie Polymersmentioning

confidence: 99%

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Photoresponsive Polymers with Aggregation-Induced Emission

Liu

et al. 2021

ACS Appl. Polym. Mater.

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Photoresponsive polymers have become one of the most important smart materials due to their unique advantages such as excellent sensitivity, high contrast, and rapid response. Endowing photoresponsive polymers with aggregation-induced emission (AIE) can not only enrich the research of materials science but also expand the applications of smart materials. Photoresponsive AIE polymers are generally constructed by combining AIE luminogens (AIEgens) with photoresponsive units via chemical, supramolecular, or physical strategies. In terms of the working mechanisms, two main responsive systems, namely, photochemical and photophysical, are summarized with specific application examples. Photoresponsive AIE polymers have been applied not only in chemosensors, photopatterning, and photodegradable materials but also in biosystems for photodynamic therapy, photothermal therapy, photoacoustic imaging, and photobiosynthesis. This Review concludes with a discussion on the challenges and perspectives for future directions in this field. All the achievements and advantages mentioned in this Review indicate the fascinating properties and bright future of photoresponsive AIE polymers.

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“…In combination with green chemistry, P‐3CP provides a facile and eco‐friendly approach to synthesize polymers due to its mild reaction conditions (low reaction temperature and in air atmosphere), high atom economy, catalyst‐free synthesis and no by‐product 14–18 . A variety of linear, 19–21 hyperbranched, 22 and dendritic 3 poly(ester amide)s have been successfully developed by P‐3CP with controlled polymer architectures.…”

Section: Introductionmentioning

confidence: 99%

L‐glutamic acid as a versatile platform for rapid synthesis of functional polyesters via facile Passerini multicomponent polymerization

Zhang

Zhao

Chen

et al. 2021

Journal of Polymer Science

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In this work, a series of polyesters with different functional side groups were successfully prepared by Passerini three‐component polymerization (P‐3CP) in “one‐pot” from biorenewable l‐glutamic acid (l‐GA)‐based monomers. First, the polymerization conditions including monomer feed ratios, solvents and comonomer were systematically studied using Boc‐protected l‐GA with adipaldehyde and tert‐butyl isocyanide. Under the optimal polymerization conditions, a variety of N‐substituted l‐GA‐based monomers as well as functional isocyanides were attempted in the P‐3CP to produce polyesters with different functionalities. Moreover, it was found that after removal of pendant protecting groups, the obtained l‐GA‐based polyester degraded spontaneously into small molecules via 1,5‐intramolecular cyclization between the pendant amine groups and the ester groups in polymer backbone. The structures and thermal properties of obtained polymers were determined by 1H NMR, IR, SEC, MALDI‐ToF‐MS, DSC, and TGA measurements. Starting from biorenewable l‐GA, this approach will provide a facile and straightforward route to produce functional and biodegradable polyesters, thus effectively expanding the range of biodegradable polymers.

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A new soft-matter material with old chemistry: Passerini multicomponent polymerization-induced assembly of AIE-active double-helical polymers with rapid visible-light degradability

Abstract: Mimicking the superstructures and functions of natural chiral materials is beneficial to understand specific biological activities in living organisms and broaden applications in the fields of chemistry and material sciences....

Cited by 24 publications

References 40 publications

Catalyst‐Free Four‐Component Polymerization of Propiolic Acids, Benzylamines, Organoboronic Acids, and Formaldehyde toward Functional Poly(propargylamine)s

Catalyst‐Free Four‐Component Polymerization of Propiolic Acids, Benzylamines, Organoboronic Acids, and Formaldehyde toward Functional Poly(propargylamine)s

Photoresponsive Polymers with Aggregation-Induced Emission

L‐glutamic acid as a versatile platform for rapid synthesis of functional polyesters via facile Passerini multicomponent polymerization

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