A multi-functional chromone-modified polyethylene obtained by metal-free C–H activation

Zhang, Yongjie; Li, Xiaopei; Zhu, Weijie; Liu, Pibo; Ren, Juntao; Chen, Shangtao; Hu, Yanming; Zhou, Guangyuan

doi:10.1039/d1py01604k

“…In 2019, Zhou and coworkers demonstrated that chromones could serve as the acceptor in a thermal C( sp 3 )−H functionalization of PE in the presence of commercially available, inexpensive DTBP as the oxidant (Scheme 2). [10] Up to 4.05 mol % functionality in P1 was yielded when the reaction was performed with 30 equivalent of chromone and 10 equivalent of DTBP in 100 wt % of melting naphthalene (NAP). The incorporation of chromone moiety onto PE exhibited several intriguing properties including antioxidation and fluorescence properties, allowing the modified samples to be used as polymer‐bound antioxidants and fluorescence markers for plastic sorting.…”

Section: Upcycling Of Polyolefins Into New Polymeric Materialsmentioning

confidence: 99%

Chemical Upcycling of Polyolefins through C−H Functionalization

Zhao,

Li,

Jiang

2023

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Polyolefins consist of abundant hydrophobic C−C and C−H bonds, and are considered as immensely potential untapped resources. Chemical upcycling offers a convenient and promising recycling strategy of polyolefins to produce newly‐functionalized polymeric materials, and high‐value added chemicals. The significant progress made in C–H functionalization reactions of alkane molecules provides new opportunities for improving polyolefin treatments. This review focuses on recent advancements in post‐modification routes, specifically the introduction of C–C and C–X (X = O, N, S, halogens and etc.) bonds onto polyolefin chain backbones, as well as degradation models involving homogeneous C–H functionalization. By emphasizing these developments, we aim to highlight the potential of chemical upcycling for enhancing the treatment of polyolefins.

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Hydroaminoalkylation for Amine Functionalization of Vinyl‐Terminated Polyethylene Enables Direct Access to Responsive Functional Materials

Ataie,

Malmir,

Scott

et al. 2024

Angewandte Chemie

0

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While functionalized polyethylenes (PEs) exhibit valuable characteristics, the constraints of existing synthetic approaches limit the variety of readily incorporated functionality. New methods to generate functionalized PEs are required to afford new applications of this common material. We report 100 % atom economic tantalum‐catalyzed hydroaminoalkylation of vinyl‐terminated polyethylene (VTPE) as a method to produce amine‐terminated PE. VTPEs with molecular weights between 2200–16800 g/mol are successfully aminated using solvent‐free conditions. Our catalytic system is efficient for the installation of both aromatic and aliphatic amines, and can be carried out on multigram scale. The associating amine functional groups afford modified material properties, as measured by water contact angle, differential scanning calorimetry (DSC) and polymer rheology. The basic amine functionality offers the opportunity to convert inert PE into stimuli‐responsive materials, such that the protonation of aminated PE affords the generation of functional antibacterial PE films.

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Hydroaminoalkylation for Amine Functionalization of Vinyl‐Terminated Polyethylene Enables Direct Access to Responsive Functional Materials

Ataie,

Malmir,

Scott

et al. 2024

Angew Chem Int Ed

0

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While functionalized polyethylenes (PEs) exhibit valuable characteristics, the constraints of existing synthetic approaches limit the variety of readily incorporated functionality. New methods to generate functionalized PEs are required to afford new applications of this common material. We report 100 % atom economic tantalum‐catalyzed hydroaminoalkylation of vinyl‐terminated polyethylene (VTPE) as a method to produce amine‐terminated PE. VTPEs with molecular weights between 2200–16800 g/mol are successfully aminated using solvent‐free conditions. Our catalytic system is efficient for the installation of both aromatic and aliphatic amines, and can be carried out on multigram scale. The associating amine functional groups afford modified material properties, as measured by water contact angle, differential scanning calorimetry (DSC) and polymer rheology. The basic amine functionality offers the opportunity to convert inert PE into stimuli‐responsive materials, such that the protonation of aminated PE affords the generation of functional antibacterial PE films.

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A multi-functional chromone-modified polyethylene obtained by metal-free C–H activation

Abstract: Post-modification of polyolefins via cutting-edge C−H activation has recently emerged as an attractive methodology for the incorporation of precise functionalities, thus expanding their applicability and creating value-added materials. In this...

Cited by 7 publications

References 46 publications

Chemical Upcycling of Polyolefins through C−H Functionalization

Chemical Upcycling of Polyolefins through C−H Functionalization

Hydroaminoalkylation for Amine Functionalization of Vinyl‐Terminated Polyethylene Enables Direct Access to Responsive Functional Materials

Hydroaminoalkylation for Amine Functionalization of Vinyl‐Terminated Polyethylene Enables Direct Access to Responsive Functional Materials

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