Phenylboronic acid functionalized polyacrylonitrile fiber for efficient and green synthesis of bis(indolyl)methane derivatives
Full Length Article|Updated:2026-01-06
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Phenylboronic acid functionalized polyacrylonitrile fiber for efficient and green synthesis of bis(indolyl)methane derivatives
Chinese Journal of Chemical EngineeringVol. 51, Issue 11, Pages: 1-9(2022)
Affiliations:
1. Department of Chemistry, School of Science, Tianjin University,Tianjin,China,300072
2. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin),Tianjin,China,300072
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Published:2022
Accepted:
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Haonan Zhang, Haotian Zhang, Minli Tao, Wenqin Zhang. Phenylboronic acid functionalized polyacrylonitrile fiber for efficient and green synthesis of bis(indolyl)methane derivatives[J]. Chinese Journal of Chemical Engineering, 2022, 51(11): 1-9.
DOI:
Haonan Zhang, Haotian Zhang, Minli Tao, Wenqin Zhang. Phenylboronic acid functionalized polyacrylonitrile fiber for efficient and green synthesis of bis(indolyl)methane derivatives[J]. Chinese Journal of Chemical Engineering, 2022, 51(11): 1-9.DOI:
Phenylboronic acid functionalized polyacrylonitrile fiber for efficient and green synthesis of bis(indolyl)methane derivatives
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
-BA
F) 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 c
atalytic activity. Further
the scale-up experiment confirmed that the fiber catalyst has a certain potential for industrial application.
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