A Triformylphloroglucinol-based Covalent Organic Polymer: Synthesis, Characterization and Its Application in Visible-light-driven Oxidative Coupling Reactions of Primary Amines

doi:10.1007/s40242-020-8008-x

高等学校化学研究 ›› 2020, Vol. 36 ›› Issue (6): 1017-1023.doi: 10.1007/s40242-020-8008-x

A Triformylphloroglucinol-based Covalent Organic Polymer: Synthesis, Characterization and Its Application in Visible-light-driven Oxidative Coupling Reactions of Primary Amines

LI Xiaodong¹, SU Qing¹, LIU Ziqian¹, LUO Kexin¹, LI Guanghua², WU Qiaolin¹

1. College of Chemistry, Jilin University, Changchun 130012, P. R. China;
2. State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun 130012, P. R. China

收稿日期:2020-06-01 修回日期:2020-08-01 出版日期:2020-12-01 发布日期:2020-12-03
通讯作者: SU Qing, WU Qiaolin E-mail:suqing@jlu.edu.cn;wuql@jlu.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.51703076).

A Triformylphloroglucinol-based Covalent Organic Polymer: Synthesis, Characterization and Its Application in Visible-light-driven Oxidative Coupling Reactions of Primary Amines

LI Xiaodong¹, SU Qing¹, LIU Ziqian¹, LUO Kexin¹, LI Guanghua², WU Qiaolin¹

1. College of Chemistry, Jilin University, Changchun 130012, P. R. China;
2. State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun 130012, P. R. China

Received:2020-06-01 Revised:2020-08-01 Online:2020-12-01 Published:2020-12-03
Contact: SU Qing, WU Qiaolin E-mail:suqing@jlu.edu.cn;wuql@jlu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.51703076).

摘要/Abstract

摘要： A triformylphloroglucinol-based A₃B₂-typed covalent organic polymer(TFG-BPTH) was successfully constructed by the condensation reaction of triformylphloroglucinol(TFG) and 2,5-bis(2-propynyloxy)terephthalo-hydrazide(BPTH) under solvothermal conditions. The structure of the TFG-BPTH was confirmed by spectra techniques including FTIR and solid-state ¹³C CP/MAS NMR spectroscopy. The mophological features of TFG-BPTH were analyzed using scanning electron microscopy(SEM) and transmission electron microscopy(TEM). The TFG-BPTH possessed good thermal and chemical stability, and exhibited good photocatalytic activity as a metal-free heterogeneous catalyst for oxidation of amines to valuable imines under visible light irradiation using O₂ as green oxidant. In addition, the catalyst could be readily recovered from the reaction mixture by simple filtration and reused for at least five cycles without any observable change in structure and catalytic activity.

关键词: Covalent organic polymer, Condensation reaction, Oxidation of amine, Photocatalysis, Heterogeneous catalysis

Abstract: A triformylphloroglucinol-based A₃B₂-typed covalent organic polymer(TFG-BPTH) was successfully constructed by the condensation reaction of triformylphloroglucinol(TFG) and 2,5-bis(2-propynyloxy)terephthalo-hydrazide(BPTH) under solvothermal conditions. The structure of the TFG-BPTH was confirmed by spectra techniques including FTIR and solid-state ¹³C CP/MAS NMR spectroscopy. The mophological features of TFG-BPTH were analyzed using scanning electron microscopy(SEM) and transmission electron microscopy(TEM). The TFG-BPTH possessed good thermal and chemical stability, and exhibited good photocatalytic activity as a metal-free heterogeneous catalyst for oxidation of amines to valuable imines under visible light irradiation using O₂ as green oxidant. In addition, the catalyst could be readily recovered from the reaction mixture by simple filtration and reused for at least five cycles without any observable change in structure and catalytic activity.

Key words: Covalent organic polymer, Condensation reaction, Oxidation of amine, Photocatalysis, Heterogeneous catalysis

LI Xiaodong, SU Qing, LIU Ziqian, LUO Kexin, LI Guanghua, WU Qiaolin. A Triformylphloroglucinol-based Covalent Organic Polymer: Synthesis, Characterization and Its Application in Visible-light-driven Oxidative Coupling Reactions of Primary Amines[J]. 高等学校化学研究, 2020, 36(6): 1017-1023.

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A Triformylphloroglucinol-based Covalent Organic Polymer: Synthesis, Characterization and Its Application in Visible-light-driven Oxidative Coupling Reactions of Primary Amines

A Triformylphloroglucinol-based Covalent Organic Polymer: Synthesis, Characterization and Its Application in Visible-light-driven Oxidative Coupling Reactions of Primary Amines

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