二维三(三氮唑)三嗪基共价有机框架用于高效光诱导分子氧活化

doi:10.1016/S1872-2067(25)64761-9

催化学报 ›› 2025, Vol. 76: 120-132.DOI: 10.1016/S1872-2067(25)64761-9

二维三(三氮唑)三嗪基共价有机框架用于高效光诱导分子氧活化

朱闪闪^a^,¹, 毛昕睿^b^,¹, 张震威^a, 杨柳柳^a, 李嘉豪^a, 李忠平^c, 金昱丞^c^,^*(), 岳惠娟^d, 刘晓明^a^,^*()

^a吉林大学化学学院, 吉林长春 130012, 中国
^b东北师范大学化学学院, 吉林长春 130024, 中国
^c蔚山国立科学技术学院(UNIST), 能源与化学工程学院/尺寸可控有机框架中心, 蔚山 44919, 韩国
^d吉林大学无机合成与制备化学国家重点实验室, 吉林长春 130012, 中国

收稿日期:2025-04-08 接受日期:2025-05-21 出版日期:2025-09-18 发布日期:2025-09-10
通讯作者: 金昱丞,刘晓明
作者简介:第一联系人：
¹共同第一作者.
基金资助:
国家自然科学基金(52373210);国家自然科学基金(52073119);吉林省自然科学基金(20230101029JC);无机合成与制备化学国家重点实验室(2024-7)

2D tris(triazolo)triazine-based covalent organic frameworks for efficient photoinduced molecular oxygen activation

Shanshan Zhu^a^,¹, Xinrui Mao^b^,¹, Zhenwei Zhang^a, Liuliu Yang^a, Jiahao Li^a, Zhongping Li^c, Yucheng Jin^c^,^*(), Huijuan Yue^d, Xiaoming Liu^a^,^*(),

^aCollege of Chemistry, Jilin University, Changchun 130012, Jilin, China
^bKey Laboratory of Polyoxometalate and Reticular Material Chemistry of Ministry of Education and Faculty of Chemistry, Northeast Normal University, Changchun 130024, Jilin, China
^cSchool of Energy and Chemical Engineering/Center for Dimension-Controllable Organic Frameworks, Ulsan National Institute of Science and Technology (UNIST), Ulsan 44919, Republic of Korea
^dState Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun 130012, Jilin, China

Received:2025-04-08 Accepted:2025-05-21 Online:2025-09-18 Published:2025-09-10
Contact: Yucheng Jin, Xiaoming Liu
About author:First author contact:
¹ Contributed equally to this work.
Supported by:
National Natural Science Foundation of China(52373210);National Natural Science Foundation of China(52073119);Natural Science Foundation of Jilin Province(20230101029JC);State Key Laboratory of Inorganic Synthesis and Preparative Chemistry(2024-7)

摘要/Abstract

摘要：

分子氧是一种廉价、丰富且环境友好的氧化剂, 但由于其三重态电子构型所导致的自旋禁阻效应, 在温和条件下难以直接氧化有机底物. 借助光催化手段, 可以实现分子氧的高效活化, 生成多种活性氧物种(ROS), 如O₂^•−, •OH, ¹O₂和H₂O₂, 这些ROS广泛应用于有机合成与能量转化领域. 然而, 分子氧的活化效率往往受限于光催化剂内部缓慢的激子解离和电荷转移动力学. 通过精确引入供体-受体(D-A)结构对共价有机框架(COF)进行分子级调控, 可有效提升电荷分离和迁移效率. 因此, 本研究通过引入D-A骨架, 实现了对分子氧的高效光诱导活化, 为构建无金属光催化体系提供了有效途径.

本文以三(三氮唑)三嗪基醛单体(TTT-TBD)为电子受体单元, 分别与吩噻嗪基三苯胺(PTz-TA)和吩恶嗪基三苯胺(PXz-TA)通过一步席夫碱缩合反应, 构筑了两种同构的三(三氮唑)三嗪基共价有机框架材料(COF-JLU61与COF-JLU62). X射线衍射分析结果表明, 两者均具备优异的结晶性; 比表面积分别为903与1404 m² g^-1, 孔径集中于约2 nm, 表现出良好的多孔性与结构稳定性. 紫外-可见光漫反射光谱及Mott-Schottky测定结果表明, 两种材料具有较宽的可见光吸收和适宜的带隙结构(E_g = 2.17与2.21 eV), 其中COF-JLU61具有更优的载流子迁移率与较小的激子束缚能(87.93 meV), 表明其具备更高的电荷分离效率. 在光催化性能评估中, COF-JLU61表现出显著优于COF-JLU62的活性. 以N,N-二甲基苯胺与N-取代马来酰亚胺为反应底物, 在可见光照射下, COF-JLU61可高效催化合成四氢喹啉类化合物, 产率高达96%以上, 并可重复使用10次以上且无明显活性衰减. 机理研究证实, O₂^•−为主要反应活性物种. 密度泛函理论(DFT)计算进一步揭示, COF-JLU61在激发态下具备更显著的电荷分离与转移行为(ΔE₆₁ = 0.14 e), 最高占有分子轨道分布于供体结构, 最低未占分子轨道集中在TTT单元, 从而有效抑制电子-空穴复合. 此外, COF-JLU61在无牺牲剂条件下展现出优异的光催化产H₂O₂能力, 在纯水中生成速率达759 μmol g^-¹ h^-¹. 旋转盘电极、旋转环盘电极、原位漫反射红外光谱测试结果表明, 反应主要由2e⁻氧还原反应与4e⁻水氧化协同驱动. DFT计算表明, COF-JLU61在H₂O₂解吸及中间态形成中表现出较低的反应能垒(0.54和1.73 eV), 有利于反应动力学过程的加速.

综上, 本研究从分子设计角度出发, 通过构建供-受体结构体系, 有效提升了COFs材料在光诱导分子氧活化过程中的性能, 为无金属、高效的COF基光催化材料的开发提供了新策略, 为人工光合成与绿色能源转化领域的研究提供了重要参考.

关键词: 共价有机框架, 三(三氮唑)三嗪, 超氧自由基阴离子, 四氢喹啉, 过氧化氢

Abstract:

Photoinduced molecular oxygen activation is crucial for artificial photosynthesis. However, metal-free semiconductor photocatalysts with high activation efficiency are still lacking up to now. Herein, two isomorphic tris(triazolo)triazine-based covalent organic frameworks were successfully constructed under solvothermal conditions. And they possess high crystallinity, inherent porosity with large surface area and good stability. Strong electron donor-acceptor skeletons expand the visible light harvesting, also facilitate the charge separation and thus lead to their superior activity of photoinduced molecular oxygen activation including photosynthesis of tetrahydroquinolines and hydrogen peroxide. This work provides a way to improve the efficiency of molecular oxygen activation through the rational design of COFs, and also opens new avenues for the construction of highly active and metal-free photocatalysts toward sustainable solar-to-chemical energy conversion.

Key words: Covalent organic frameworks, Tris(triazolo)triazine, Superoxide radical anion, Tetrahydroquinolines, Hydrogen peroxide

朱闪闪, 毛昕睿, 张震威, 杨柳柳, 李嘉豪, 李忠平, 金昱丞, 岳惠娟, 刘晓明. 二维三(三氮唑)三嗪基共价有机框架用于高效光诱导分子氧活化[J]. 催化学报, 2025, 76: 120-132.

Shanshan Zhu, Xinrui Mao, Zhenwei Zhang, Liuliu Yang, Jiahao Li, Zhongping Li, Yucheng Jin, Huijuan Yue, Xiaoming Liu, . 2D tris(triazolo)triazine-based covalent organic frameworks for efficient photoinduced molecular oxygen activation[J]. Chinese Journal of Catalysis, 2025, 76: 120-132.

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https://www.cjcatal.com/CN/Y2025/V76/I9/120

图/表 7

Fig. 1. (a) Syntheses of COF-JLUs. (b) Top and (c) side views of COF-JLU61. (d) Top and (f) side views of COF-JLU62 (Color code: light gray, carbon; blue, nitrogen; yellow, sulfur; red, oxygen; hydrogen is omitted for clarity).

Fig. 2. (a) The experimental and simulated PXRD profiles of COF-JLU61 and (b) COF-JLU62. (c) SEM image of COF-JLU61 and (d) COF-JLU62. (e) TEM image of COF-JLU61 and (f) COF-JLU62.

Fig. 3. FT-IR spectra of COF-JLU61 (a) and (b) COF-JLU62, and their corresponding monomers. The chemical structure and 13C CP-MAS NMR spectra of COF-JLU61 (c) and COF-JLU62 (d). N2 sorption isotherm of COF-JLU61 (e) and COF-JLU62 (f) at 77 K. Insets: the corresponding pore size distribution (solid circles for adsorption and open circles for desorption).

Fig. 4. (a) UV-vis DRS spectrum of COF-JLUs; inset: its photograph. (b) Tauc plots of COF-JLUs. (c) Band structures diagram of two COF-JLUs (the electrochemical potential at pH = 7.0). (d) Transient current density of COF-JLU61 and COF-JLU62. (e) EIS spectra of COF-JLU61 and COF-JLU62. (f) Transition photocurrents of COF-JLUs under visible-light illumination. Integrated PL emission intensity as a function of the temperature of COF-JLU61 (g) and COF-JLU62 (h). Inset: the corresponding temperature-dependent PL spectra.

Table 1 Substrate scope for photocatalytic tetrahydroquinolines.

Fig. 5. (a) The photocatalytic tetrahydroquinoline of COF-JLU61 under different conditions. (b) EPR conduction band electrons spectra of COF-JLU61 and COF-JLU62 in the dark and during visible light irradiation. (c) Calculated band structure and density of states of COF-JLU61. (d) Kohn-Sham orbitals of HOMO and LUMO of COF-JLU61. (e) Charge density difference excited states of the model compound (COF-JLU61). (f) Charge density difference excited states of the model compound (COF-JLU62). The green and blue orbitals represent electron and hole distribution, respectively.

Fig. 6. (a) Time-dependent H2O2 photogeneration using visible light for COF-JLU61 and COF-JLU62 (Conditions: 5 mg of catalyst in 50 mL of pure water, O2 atmosphere and air atmosphere, AM 1.5, average light intensity: 100 mW cm−2). (b) The H2O2 production of COF-JLU61 and COF-JLU62 under different conditions (AM 1.5, average light intensity: 100 mW cm−2). (c) The Koutecky-Levich plots obtained by RDE measurements (vs. Ag/AgCl). (d) RRDE voltammograms obtained in 0.1 mol L−1 phosphate buffer solution with a scan rate of 10 mV s−1 and a rotation rate of 1000 rpm. The potential of the Pt ring electrode is set at −0.23 V (vs. Ag/AgCl) to detect O2. (e) DRIFTS spectra of COF-JLU61 in H2O2 photosynthesis (dark and light). (f) Distributions of the photo-excited electrons and holes (yellow and blue represent electrons and holes, respectively). (g) Gibbs free energy diagrams of H2O2 photogeneration over COF-JLUs by 2e− ORR paths, and (h) Gibbs free energy diagrams of O2 photogeneration by 4e− WOR path by the DFT calculations.

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二维三(三氮唑)三嗪基共价有机框架用于高效光诱导分子氧活化

2D tris(triazolo)triazine-based covalent organic frameworks for efficient photoinduced molecular oxygen activation

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