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

doi:10.1016/j.cjche.2021.08.029

中国化学工程学报 ›› 2022, Vol. 51 ›› Issue (11): 1-9.DOI: 10.1016/j.cjche.2021.08.029

• Full Length Article • 下一篇

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

Haonan Zhang¹, Haotian Zhang¹, Minli Tao^1,2, Wenqin Zhang^1,2

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

收稿日期:2021-06-25 修回日期:2021-08-30 出版日期:2022-11-18 发布日期:2023-01-18
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).

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

Haonan Zhang¹, Haotian Zhang¹, Minli Tao^1,2, Wenqin Zhang^1,2

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:2022-11-18 Published:2023-01-18
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).

摘要/Abstract

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 (PAN_p-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

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 (PAN_p-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

Haonan Zhang, Haotian Zhang, Minli Tao, Wenqin Zhang. Phenylboronic acid functionalized polyacrylonitrile fiber for efficient and green synthesis of bis(indolyl)methane derivatives[J]. 中国化学工程学报, 2022, 51(11): 1-9.

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

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

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