SCI和EI收录∣中国化工学会会刊

Chinese Journal of Chemical Engineering ›› 2022, Vol. 51 ›› Issue (11): 1-9.DOI: 10.1016/j.cjche.2021.08.029

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Phenylboronic acid functionalized polyacrylonitrile fiber for efficient and green synthesis of bis(indolyl)methane derivatives

Haonan Zhang1, Haotian Zhang1, Minli Tao1,2, Wenqin Zhang1,2   

  1. 1. Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China;
    2. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China
  • Received:2021-06-25 Revised:2021-08-30 Online:2023-01-18 Published:2022-11-18
  • Contact: Minli Tao,E-mail:mltao@tju.edu.cn;Wenqin Zhang,E-mail:wqzhang@tju.edu.cn
  • Supported by:
    This work was financially supported by the National Natural Science Foundation of China (21777111).

Phenylboronic acid functionalized polyacrylonitrile fiber for efficient and green synthesis of bis(indolyl)methane derivatives

Haonan Zhang1, Haotian Zhang1, Minli Tao1,2, Wenqin Zhang1,2   

  1. 1. Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China;
    2. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China
  • 通讯作者: Minli Tao,E-mail:mltao@tju.edu.cn;Wenqin Zhang,E-mail:wqzhang@tju.edu.cn
  • 基金资助:
    This work was financially supported by the National Natural Science Foundation of China (21777111).

Abstract: The use of fiber as a catalyst carrier to construct heterogeneous catalysts with good catalytic activity and recycling performance has received wide attention. In this study, three phenylboronic acid functionalized polyacrylonitrile fiber (PANF) catalysts were synthesized by amination and quaternization. Fourier transform infrared spectroscopy, X-ray diffractometry, scanning electron microscopy, and X-ray photoelectron spectroscopy were used to verify the successful grafting of phenylboronic acid and the structural integrity of the fiber catalyst after recycling. The activity of the catalysts was explored with the Friedel–Crafts alkylation between indole and aromatic aldehydes. The results indicate that the synthesized catalyst (PANp-BAF) in which the phenylboronic acid functional group was linked at the para position, exhibited the highest catalytic activity for the Friedel–Crafts alkylation. The substrate scope experiments confirmed that the catalyst has outstanding catalytic activity for most aromatic aldehydes, especially for those containing moderate electron donating groups. Moreover, the catalyst can be reused eight times in water without significant decrease in its catalytic activity. Further, the scale-up experiment confirmed that the fiber catalyst has a certain potential for industrial application.

Key words: Polymers, Phenylboronic acid, Catalyst support, Friedel–Crafts alkylation, Sustainability

摘要: The use of fiber as a catalyst carrier to construct heterogeneous catalysts with good catalytic activity and recycling performance has received wide attention. In this study, three phenylboronic acid functionalized polyacrylonitrile fiber (PANF) catalysts were synthesized by amination and quaternization. Fourier transform infrared spectroscopy, X-ray diffractometry, scanning electron microscopy, and X-ray photoelectron spectroscopy were used to verify the successful grafting of phenylboronic acid and the structural integrity of the fiber catalyst after recycling. The activity of the catalysts was explored with the Friedel–Crafts alkylation between indole and aromatic aldehydes. The results indicate that the synthesized catalyst (PANp-BAF) in which the phenylboronic acid functional group was linked at the para position, exhibited the highest catalytic activity for the Friedel–Crafts alkylation. The substrate scope experiments confirmed that the catalyst has outstanding catalytic activity for most aromatic aldehydes, especially for those containing moderate electron donating groups. Moreover, the catalyst can be reused eight times in water without significant decrease in its catalytic activity. Further, the scale-up experiment confirmed that the fiber catalyst has a certain potential for industrial application.

关键词: Polymers, Phenylboronic acid, Catalyst support, Friedel–Crafts alkylation, Sustainability