二维酞菁共价有机框架材料用于红外光光催化

doi:10.1016/S1872-2067(24)60196-8

催化学报 ›› 2025, Vol. 69: 271-281.DOI: 10.1016/S1872-2067(24)60196-8

二维酞菁共价有机框架材料用于红外光光催化

詹晓宁, 金昱丞, 韩彬(), 周子文, 陈宝通, 丁旭, 李福顺, 索植孺, 姜蓉(), 齐冬冬, 王康, 姜建壮()

北京科技大学化学系,功能分子与晶态材料科学与应用北京市重点实验室, 北京材料基因组工程高级创新中心, 北京 100083

收稿日期:2024-10-09 接受日期:2024-11-07 出版日期:2025-02-18 发布日期:2025-02-10
通讯作者: *电子信箱: hanbin@ustb.edu.cn (韩彬), hazelj999@163.com (姜蓉), jianzhuang@ustb.edu.cn (姜建壮).
基金资助:
中国国家自然科学基金(22205015);中国国家自然科学基金(22175020);中国国家自然科学基金(22235001);国家博士后创新人才计划(BX20220032);中国博士后科学基金资助项目(2022BG013);中央高校基本科研业务费专项资金(00007709);中央高校基本科研业务费专项资金(00007770);北京科技大学

2D Phthalocyanine-based covalent organic frameworks for infrared light-mediated photocatalysis

Xiaoning Zhan, Yucheng Jin, Bin Han(), Ziwen Zhou, Baotong Chen, Xu Ding, Fushun Li, Zhiru Suo, Rong Jiang(), Dongdong Qi, Kang Wang, Jianzhuang Jiang()

Affiliation Beijing Advanced Innovation Center for Materials Genome Engineering, Beijing Key Laboratory for Science and Application of Functional Molecular and Crystalline Materials, Department of Chemistry, University of Science and Technology Beijing, Beijing 100083, China

Received:2024-10-09 Accepted:2024-11-07 Online:2025-02-18 Published:2025-02-10
Contact: *E-mail: hanbin@ustb.edu.cn (B. Han), hazelj999@163.com (R. Jiang), jianzhuang@ustb.edu.cn (J. Jiang).
Supported by:
Natural Science Foundation of China(22205015);Natural Science Foundation of China(22175020);Natural Science Foundation of China(22235001);National Postdoctoral Program for Innovative Talents(BX20220032);China Postdoctoral Science Foundation Funded Project(2022BG013);Fundamental Research Funds for the Central Universities(00007709);Fundamental Research Funds for the Central Universities(00007770);University of Science and Technology Beijing

摘要/Abstract

摘要：

红外光在太阳光中具有近一半的高占比, 开发新型红外光光催化剂高效利用红外光是研究的热点. 共价有机框架(COF)由于其良好的稳定性、规则排列堆叠、出色的光捕获能力以及在光激发状态下的有效电荷分离和转移等特性, 在光催化领域具有良好的应用前景. 然而, COF光催化剂由于有限的电子吸收, 在红外光下的催化研究极少.

本文通过2,3,9,10,16,17,23,24-四酸酐金属酞菁(M(TAPc))与9,10-二苯基蒽(DPA)的酰亚胺化反应制备了两例新型的二维聚酰亚胺连接的酞菁COFs, 即MPc-DPA-COF (M=Zn/Cu). 粉末X射线衍射分析和高分辨率透射电子显微镜结果表明, 两例COFs均具有高度结晶的AA堆叠结构, 相邻层间距为0.33 nm. 固体紫外-可见漫反射光谱结果表明, 二维COFs相邻层中酞菁发色团之间的有效π-π相互作用导致了MPc-DPA-COF的Q带相对于M(TAPc)单体的窄Q带(697 nm)红移至760-1000 nm的红外光吸收范围, 这表明该材料具有利用红外光进行光催化的可行性. 电子自旋共振光谱测试结果证明, ZnPc-DPA-COF在红外光辐射(λ > 760 nm)下具有较好的生产超氧自由基(^•O₂^-)和单线态氧(¹O₂)的性能, 从而具有优秀的红外光光催化氧化一系列种类的硫化物(带有不同的吸电子基团或供电子基团)的能力. 相应的淬灭实验结果揭示了^•O₂^-和¹O₂二者对硫化物氧化的贡献, 特别是^•O₂^-物种在该光催化过程中起着主导作用. 密度泛函理论分析结果表明, ZnPc-DPA-COF具有比低能红外光(< 1.64 eV)更低的光学带隙, 且吸附模型、电荷密度图以及分波态密度图证明了中心金属锌对氧气有着强吸附能力, 这为制备高效的红外光催化剂提供了理论依据.

综上所述, 本文通过将M(TAPc)与DPA连接制备了新型聚酰亚胺连接的二维酞菁COF. 相比于酞菁单体, 该COFs材料在红外光范围具有强烈吸收, 可以利用红外光高效生产活性氧物种, 进而实现在红外光下催化硫醚氧化反应. 本研究结果不仅提供了一种新型高效的红外光光催化剂, 还揭示了酞菁基COF在光催化方面的巨大应用潜力.

关键词: 共价有机框架, 红外光, 光催化, 活性氧物种, 硫化物氧化

Abstract:

Covalent organic frameworks (COFs) based photocatalysts utilizing infrared light remains unexplored due to the limitation of electronic absorption. Herein, two novel two-dimensional (2D) polyimide-linked phthalocyanine COFs, namely MPc-DPA-COFs (M = Zn/Cu), were prepared from the imidization reaction of metal tetraanhydrides of 2,3,9,10,16,17,23,24-octacarboxyphthalocyaninato (M(TAPc)) with 9,10-diphenyl anthracene (DPA). Both COFs possess highly crystalline eclipsed AA stacking structure with neighboring layer distance of 0.33 nm on the basis of powder X-ray diffraction analysis and high-resolution transmission electron microscopy. Effective π-π interaction between phthalocyanine chromophores in neighboring layers of 2D COFs leads to significant bathochromic-shift of narrow Q band from 697 nm for M(TAPc) to the infrared light absorption range of 760-1000 nm for MPc-DPA-COFs according to solid UV-vis diffuse reflectance spectra. This endows them in particular ZnPc-DPA-COF with excellent reactive oxygen species of ^•O₂⁻ and ¹O₂ generation activity under infrared light radiation (λ > 760 nm) based on the electron spin resonance spectroscopy measurement, in turn resulting in the excellent photocatalytic capacity towards oxidation of sulfides under infrared light radiation. Corresponding quenching experiments reveal the contribution of both ^•O₂⁻ and ¹O₂ to the oxidation of sulfides, but the former ^•O₂⁻ species plays a leading role in this photocatalytic process. The present result not only provides a new efficient infrared light photocatalyst but also unveils the good potentials of phthalocyanine-based COFs in photocatalysis.

Key words: Covalent organic framework, Infrared light, Photocatalysis, Reactive oxygen species, Oxidation of sulfides

詹晓宁, 金昱丞, 韩彬, 周子文, 陈宝通, 丁旭, 李福顺, 索植孺, 姜蓉, 齐冬冬, 王康, 姜建壮. 二维酞菁共价有机框架材料用于红外光光催化[J]. 催化学报, 2025, 69: 271-281.

Xiaoning Zhan, Yucheng Jin, Bin Han, Ziwen Zhou, Baotong Chen, Xu Ding, Fushun Li, Zhiru Suo, Rong Jiang, Dongdong Qi, Kang Wang, Jianzhuang Jiang. 2D Phthalocyanine-based covalent organic frameworks for infrared light-mediated photocatalysis[J]. Chinese Journal of Catalysis, 2025, 69: 271-281.

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图/表 7

Scheme 1. Synthesis of ZnPc-DPA-COF and CuPc-DPA-COF.

Fig. 1. PXRD patterns of ZnPc-DPA-COF (a) and CuPc-DPA-COF (b). Simulated packing structures of ZnPc-DPA-COF (c,d) and CuPc-DPA-COF (e,f) via π-π interactions (C: gray; N: cyan; O: red; Zn: violet; Cu: orange; H: white). SEM, TEM, HRTEM, and EDS mapping photos for ZnPc-DPA-COF (g?j) and CuPc-DPA-COF (k?n).

Fig. 2. FT-IR spectra (a), XPS spectrum (b), and N2 adsorption (solid) and desorption (hollow) curves (c) at ?196 °C of ZnPc-DPA-COF. XANES spectra (d) and EXAFS curves (e) of Zn foil, ZnPc, and ZnPc-DPA-COF at Zn K-edge. (f) The experimental and fitting EXAFS curves of ZnPc-DPA-COF. WT-EXAFS of ZnPc-DPA-COF (g), ZnPc (h), and Zn foil (i).

Fig. 3. (a) EIS curves. Solid and liquid UV-vis spectra (Insert: Nyquist plots) of ZnPc-DPA-COF (b) and CuPc-DPA-COF (c). Mott-Schottky plots of ZnPc-DPA-COF (d) and CuPc-DPA-COF (e). (f) Experimental energy levels of ZnPc-DPA-COF and CuPc-DPA-COF.

Fig. 4. (a) Time-dependent catalytic efficiency of ZnPc-DPA-COF under infrared light. (b) Selective oxidation of organic sulfide yield by photocatalysis of ZnPc-DPA-COF for 4.0 h in O2 atmosphere. (c) Recycling test of ZnPc-DPA-COF. (d) The number of photocatalysts reported for sulfide oxidation reactions under different types of light irradiation in the past three years. ESR detection of 1O2 generation trapped by TEMP (e) and ?O2? generation trapped by DMPO (f). (g) Quenching experiments on the photocatalytic oxidation of methylphenyl-sulfide. (h) Plausible mechanism for this photocatalytic oxidation reaction.

Table 1 Photocatalytic oxidation of sulfides to sulfoxide under different conditions a.

Entry	Substrate	Time (h)	Conv.^b (%)	Sel. (%)	TOF (mmol g⁻¹ h⁻¹)
1	R = H	8	>99	>99	6.25
2^c	R = H	8	trace	trace	trace
3^d	R = H	8	trace	trace	trace
4^e	R = H	8	trace	trace	trace
5^f	R = H	8	trace	trace	trace
6^g	R = H	8	83	>99	5.19
7^h	R = H	8	trace	trace	trace
8	R = CH₃	7	>99	>99	7.14
9	R = OCH₃	4	>99	>99	12.5
10	R = Cl	8	69	>99	4.31
11	R = NO₂	8	53	>99	3.31

Fig. 5. (a) The distribution of orbital electron wavefunctions of ZnPc-DPA-COF. The charge density of ZnPc-DPA-COF (b) and CuPc-DPA-COF (c). The EDD diagram of ZnPc-DPA-COF (d) and CuPc-DPA-COF (e). (f) The ESP diagram of ZnPc-DPA-COF. (g) O2 adsorption models. (h) The differential charge density maps of ZnPc-DPA-COF and CuPc-DPA-COF and the charge density differences of adsorbed O2 on ZnPc-DPA-COF and CuPc-DPA-COF. The cyan and yellow areas represented electron increase and decrease, respectively. (i) The overlap of O (2p) & Zn (3dz2) in pDOS. (j) The Gibbs free energy diagram for the reaction pathways.

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二维酞菁共价有机框架材料用于红外光光催化

2D Phthalocyanine-based covalent organic frameworks for infrared light-mediated photocatalysis

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