Research Progress of Porphyrin-Based Covalent Organic Frameworks in Photocatalysis★

doi:10.6023/A23040178

Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (7): 784-792.DOI: 10.6023/A23040178 Previous Articles Next Articles

Special Issue: 庆祝《化学学报》创刊90周年合辑

Perspective

卟啉基共价有机框架的光催化研究进展^★

何明慧, 叶子秋, 林桂庆, 尹晟, 黄心翊, 周旭, 尹颖, 桂波, 汪成^*()

武汉大学化学与分子科学学院武汉 430072

投稿日期:2023-04-28 发布日期:2023-06-05

作者简介:

何明慧, 硕士毕业于浙江师范大学, 现为武汉大学化学与分子科学学院博士生, 目前研究方向为共价有机框架的构筑及其催化性能的探究.

汪成, 2003年获武汉大学学士学位, 2008年在中国科学院化学研究所获理学博士学位, 随后在美国西北大学化学系进行博士后研究. 2012年4月加入武汉大学化学与分子科学学院, 任教授、博士生导师. 2013年被聘为湖北省“楚天学者”特聘教授, 2015年获得湖北省杰出青年基金资助, 2019年入选第四批“万人计划”青年拔尖人才, 2022年获国家杰出青年科学基金资助, 任Chinese Journal of Chemistry编委、中国化学会超分子化学专业委员会委员、中国化学会晶体化学专业委员会委员. 主要从事共价有机框架(COFs)的研究.

^★庆祝《化学学报》创刊90周年.

基金资助:
国家自然科学基金(22225503); 国家自然科学基金(U21A20285)

Research Progress of Porphyrin-Based Covalent Organic Frameworks in Photocatalysis^★

Minghui He, Ziqiu Ye, Guiqing Lin, Sheng Yin, Xinyi Huang, Xu Zhou, Ying Yin, Bo Gui, Cheng Wang()

College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072

Received:2023-04-28 Published:2023-06-05
Contact: *E-mail: chengwang@whu.edu.cn
About author:
^★Dedicated to the 90th anniversary of Acta Chimica Sinica.
Supported by:
National Natural Science Foundation of China(22225503); National Natural Science Foundation of China(U21A20285)

Covalent organic frameworks (COFs) are a class of crystalline organic porous materials formed by molecular building blocks via covalent bonds. According to the dimensions of the framework extended in space, COFs can be divided into two-dimensional and three-dimensional COFs. Owing to their high specific surface area, good stability and strong designability, COFs have broad prospects in the fields of gas adsorption and separation, catalysis, sensing, optoelectronics, and energy storage. In the field of photocatalysis, COFs have the following advantages. First, COFs are highly designable, which can achieve efficient photocatalysis by introducing different functional units to adjust the band gap energy and light absorption range. Secondly, the ordered structure of COFs improves the electron-hole separation efficiency. In addition, the high specific surface area and abundant active sites of COFs can promote the photocatalytic reaction and improve the reaction rate. Finally, COFs are connected by covalent bonds, which make them highly stable and facilitate the maintenance of catalytic activity in the photocatalytic process. Porphyrins are a class of 18 π-electron conjugated macrocyclic compounds formed by the interconnection of four pyrroles, which can be involved in photosynthesis as the core part of chlorophyll and other biomolecules. As a kind of functional units with large π-conjugated structure and good photophysical properties, porphyrins usually have strong absorption in the 400~450 nm (Soret band) and 500~700 nm (Q band) regions, and their photocatalytic properties can be regulated by coordination with metal ions and modification of functional groups, which has unique advantages in the field of photocatalysis. By introducing porphyrins into COFs, combined with their unique advantages, porphyrin-based COFs have been found great potential in the field of photocatalysis due to the exceptional optical absorption in a broad spectral range, multiple active sites and effective electron-hole separation ability. As a new type of photocatalyst, porphyrin-based COFs have attracted much interest and have been rapidly developed in the field of photocatalysis. In this review, we focus on the discussion of porphyrin-based COFs in the photocatalytic CO₂ reduction, photocatalytic water splitting, photocatalytic organic transformation, and photocatalytic reduction of hexavalent uranium. Finally, the prospects and challenges of porphyrin-based COFs in photocatalysis are discussed.

Key words: covalent organic framework, porphyrin, photocatalysis

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Minghui He, Ziqiu Ye, Guiqing Lin, Sheng Yin, Xinyi Huang, Xu Zhou, Ying Yin, Bo Gui, Cheng Wang. Research Progress of Porphyrin-Based Covalent Organic Frameworks in Photocatalysis^★[J]. Acta Chimica Sinica, 2023, 81(7): 784-792.

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Fig. & Tab. 7

Figure 1. (a) Schematic diagram of the mechanism of TTCOF-M (M=2H, Zn, Ni, Cu) CO2 reduction reaction with H2O oxidation and (b) theoretical simulation UV-Vis diffuse reflectance spectroscopy of TTCOF-Zn and scheme of photoinduced electron transfer (PET) route under light excitation (inset)

Figure 2. (a) Schematic diagram for construction of TAPP-HFPB-COF, (b) band alignment of TAPP-HFPB-COF, (c) photocatalytic CO2 reduction performance of TAPP-HFPB-COF upon visible-light irradiation within 6 h (red curve: CO; blue curve: CH4), (d) synthesis of JUC-640-M (M=2H, Co, Ni), (e) the photocatalytic activity of JUC-640-M and (f) free energy diagrams for CO2 reduction to CO on JUC-640-M (M=Co, Ni) under the same condition

Figure 3. (a) Schematic diagram for construction of MPor-DETH-COF (M?=?2H, Co, Ni, Zn), (b) time dependent H2 photogeneration using visible light for MPor-DETH-COF (M?=?2H, Co, Ni, Zn) [2.5?mg catalyst in 5?mL phosphate buffer solution, 2.5?μL H2PtCl6 aqueous solution (w=8%), 50?μL triethanolamine (TEOA), λ?>?400?nm 300?W Xe lamp] and (c) long-term H2 production using visible light for ZnPor-DETH-COF for 120?h.

Figure 4. (a) Schematic diagram for construction of Por-sp2c-COF and (b) oxidative coupling of dibenzylamine using the COFs as photocatalyst [[Ⅰ] Conditions: Dibenzylamine (0.1 mmol), photocatalyst (9.67 mg), CH3CN (1 mL), chlorobenzene (10 μL), irradiation with 3 W white LEDs for 0.5 h. [Ⅱ] Conversion determined by GC-FID with chlorobenzene as the internal standard. [Ⅲ]?Por-COF (8.71 mg). [Ⅳ] Benzoquinone was used as a superoxide scavenger (1 mg)]

Figure 5. Schematic diagram of a plausible mechanism of visible-light-induced selective aerobic oxidation of benzylamine by cooperative Por-sp2c-COF photocatalysis and TEMPO catalysis

Figure 6. (a) Schematic diagram for construction of 2D-PdPor-COF and 3D-PdPor-COF, structural representations of 2D-PdPor-COF (b) and 3D-PdPor-COF (d), diagrams of the stacking of palladium porphyrin units in 2D-PdPor-COF (c) and 3D-PdPor-COF (e) and (f) photocatalytic production of methyl phenyl sulfoxide from the selective oxidation of thioanisole under the catalysis of 2D-PdPor-COF and 3D-PdPor-COF

Figure 7. (a) Crystal structure of DhaTph-M (M=Zn and Ni) and diagram representation of their discriminative oxygen activation selectivity to 1O2 and O2?－ under visible light irradiation and (b) photocatalytic oxidation of α-terpinene over different catalysts in O2 atmosphere under visible light irradiationI [IReaction conditions: catalyst (10 mg), α-terpinene (0.1 mmol), 3 mL of CH3CN, 300 W Xe lamp with visible light (λ>420 nm), O2 (101 kPa). IIYield of products was analyzed by GC, and n-dodecane was used as the internal standard]

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卟啉基共价有机框架的光催化研究进展^★

Research Progress of Porphyrin-Based Covalent Organic Frameworks in Photocatalysis^★

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卟啉基共价有机框架的光催化研究进展★

Research Progress of Porphyrin-Based Covalent Organic Frameworks in Photocatalysis★

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卟啉基共价有机框架的光催化研究进展^★

Research Progress of Porphyrin-Based Covalent Organic Frameworks in Photocatalysis^★