A Triformylphloroglucinol-based Covalent Organic Polymer: Synthesis, Characterization and Its Application in Visible-lig
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doi: 10.1007/s40242-020-8008-x
Article
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 and 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; 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)terephthalohydrazide(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 O 2 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. Keywords Covalent organic polymer; Condensation reaction; Oxidation of amine; Photocatalysis; Heterogeneous catalysis
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Introduction
Photocatalysis has emerged as an attractive and sustainable approach to address the current energy and environmental challenges[1]. Such a photochemical transformation has been well-known for green plants through natural photosynthsis[2]. Since the breakthrough discovery by Fujishima and Honda in 1972[3], intensive efforts have been devoted to a broad range of photocatalytic applications including water splitting, CO2 reduction, organic transformation and degradation of organic dyes[4]. To date, various homogeneous and heterogeneous photosensitizers(PS) have been widely employed in these photocatalytic transformations[5]. As compared to those homogenous systems, heterogeneous photocatalysts have considerable advantages in terms of structural robustness, low cost, non-toxicity and good recyclability[6]. Therefore, the development of highly efficient and environmentally benign heterogeneous photocatalysts is highly desired. In recent years, covalent organic polymers(COPs), emerging as a new type of polymer material, have been developed and widely applied in gas separation and storage[7], energy storage[8], catalysis[9,10] and fluorescent sensors[11], due to their versatile structures, robust porosity, high thermochemical stability, and rich π-conjugated system. Interestingly, the photoelectric properties of COPs could be easily tailored at molecular level by incorporating functional components, and
thus received growing interests in the field of
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