氧中心有机自由基最新研究进展: 表征、合成及应用

doi:10.1016/S1872-2067(26)65144-3

催化学报 ›› 2026, Vol. 88: 183-206.DOI: 10.1016/S1872-2067(26)65144-3

氧中心有机自由基最新研究进展: 表征、合成及应用

刘淑芳^a^,¹, 陈锋宇^a^,¹, 李思媛^a, 叶宇昕^a^,^*(), 欧阳钢锋^a^,^b^,^*()

^a 中山大学化学工程与技术学院, 绿色化学与分子工程研究院, 水产动物疫病防控与健康养殖全国重点实验室, 南方海洋科学与工程广东省实验室(珠海), 广东珠海 519082
^b 中山大学化学学院, 生物无机与合成化学教育部重点实验室, Lehn功能材料研究所, 绿色化学与分子工程研究院, 广东广州 510275

收稿日期:2025-12-20 接受日期:2026-02-22 出版日期:2026-09-18 发布日期:2026-09-05
通讯作者: *电子信箱: yeyuxin5@mail.sysu.edu.cn (叶宇昕),
cesoygf@mail.sysu.edu.cn (欧阳钢锋).
基金资助:
国家自然科学基金(22336007);国家自然科学基金(22422611);国家自然科学基金(22206209);南方海洋科学与工程广东省实验室(珠海)(SML2024SP003);广东省功能分子工程重点实验室基础研究卓越中心项目(31000-42080002)

Recent advances in oxygen-centered organic radicals: Characterization, synthesis, and applications

Shufang Liu^a^,¹, Fengyu Chen^a^,¹, Siyuan Li^a, Yu-Xin Ye^a^,^*(), Gangfeng Ouyang^a^,^b^,^*()

^a State Key Laboratory of Biocontrol, School of Chemical Engineering and Technology, Southern Marine Science and Engineering Guangdong Laboratory (Zhuhai), IGCME, Sun Yat-sen University, Zhuhai 519082, Guangdong, China
^b Key Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education, LIFM, School of Chemistry, IGCME, Sun Yat-sen University, Guangzhou 510275, Guangdong, China

Received:2025-12-20 Accepted:2026-02-22 Online:2026-09-18 Published:2026-09-05
About author:Yu-Xin Ye (School of Chemical Engineering and Technology, Sun Yat-sen University) received her B.S. degree from Sun Yat-sen University in 2011 and Ph.D. degree in 2017. From 2018 to 2023, she conducted postdoctoral research under the supervision of Professor Ouyang Gangfeng. She joined the School of Chemical Engineering and Technology at Sun Yat-sen University in 2023. She is Excellent Young Scientists of National Natural Science Foundation of China (2024). She has published over 20 papers as the first or corresponding author in prestigious journals such as Nat. Water., Proc. Natl. Acad. Sci. U.S.A., Adv. Mater., Chin. J. Catal., Nat. Commun., and Angew. Chem. Int. Ed. Her research focuses on the design of novel organic photocatalysts, the characterization and regulation of photophysical and photochemical processes, photocatalytic synthesis and application of hydrogen peroxide, and photocatalytic degradation of environmental pollutants.
Gangfeng Ouyang (School of Chemical Engineering and Technology, Sun Yat-sen University) received his B.S. degree from Sichuan University in 1992 and his M.S. degree from the School of Chemistry and Chemical Engineering, Sun Yat-sen University in 1995. He subsequently joined the faculty of the same school at Sun Yat-sen University, first as a Teaching Assistant and then as a Lecturer. He earned his Ph.D. degree from the School of Chemistry and Chemical Engineering, Sun Yat-sen University in 2003. He then pursued postdoctoral research in Professor Pawliszyn Janusz's group at the University of Waterloo, Canada. He is Distinguished Young Scholars Recipients of National Natural Science Foundation of China (2012). Professor Ouyang has authored/co-authored over 320 SCI-indexed publications in prestigious journals such as Chem. Rev., PNAS, Chem., Nat. Commun., Angew. Chem. Int. Ed., Chem. Sci., Anal. Chem., and Environ. Sci. Technol., with over 8,000 citations. His research primarily focuses on environmental analytical chemistry and microextraction techniques, with applications in water analysis, in vivo analysis in plants and animals, and medical diagnostics. His research interests include environmental analytical chemistry, environmental pollution control, and bioanalysis.
First author contact:1 共同第一作者.
1 Contributed equally to this work.
Supported by:
The National Natural Science Foundation of China(22336007);The National Natural Science Foundation of China(22422611);The National Natural Science Foundation of China(22206209);The Southern Marine Science and Engineering Guangdong Laboratory (Zhuhai)(SML2024SP003);The Guangdong Basic Research Center of Excellence for Functional Molecular Engineering Project(31000-42080002)

摘要/Abstract

摘要：

近年来, 传统活性氧物种(ROS)虽具有高反应活性, 却因选择性差、易引发底物过度矿化、寿命短暂(微秒至毫秒级)且依赖捕获剂检测等固有局限, 难以满足精准氧化过程对可控性的要求. 与之形成鲜明对比的是, 氧中心有机自由基(OCORs)凭借其未配对电子在π-共轭体系中的高度离域, 获得了显著的动力学稳定性, 使其寿命由分钟级延长至数年, 且无需捕获剂即可直接检测. 更重要的是, OCORs兼具高反应活性与可调的氧化还原特性, 不仅可作为选择性氧化的关键中间体, 还能通过结构转化在自然及人工光催化系统中发挥高效的电子介导作用. 这种兼具稳定性与可调控性的电子构型, 使其在光合作用模拟、环境修复等诸多前沿领域展现出广阔的应用前景.
本文系统介绍了OCORs的表征方法、前驱体合成策略及其在光催化领域的研究进展. 首先, 从经典的基于醌/氢醌氧化还原过程的芳氧自由基和半醌型自由基出发, 梳理了OCORs的发展脉络, 阐述了其未配对电子离域于扩展π共轭体系所赋予的独特电子结构. 在表征方法上, OCORs的鉴定需采用多技术联用策略: 电子顺磁共振可提供最直接的自由基证据, 但常需结合自由基捕获实验进行定性确认; 氧气消耗测试可作为间接表征手段; 电化学方法与原位振动光谱有助于解析反应机理与中间体结构; 而密度泛函理论计算则为OCORs的指认提供理论支撑. 这种多模式协同方法突破了单一技术的局限, 是实现OCORs精准鉴定的关键. 在前驱体合成策略方面, 本文归纳了以醌类和蒽醌类化合物为前体, 通过Suzuki-Miyaura偶联、Sonogashira-Hagihara偶联、Buchwald-Hartwig胺化及酚醛缩合等反应构筑OCORs前驱体的模块化合成路线. 在光催化应用领域, OCORs作为关键活性中间体展现出多方面的优异性能: 在光催化合成过氧化氢、二氧化碳还原制备高附加值化学品等反应中, OCORs可显著提升催化效率; 在环境修复领域, OCORs作为长寿命中间体参与水体酚类污染物降解, 兼具高选择性与高效性; 在光催化杀菌方面, 可实现低光强下细菌的高效失活; 在有机合成中, 凭借其优异的电子转移能力, 成功应用于C(sp³)-H键光氧化反应的选择性调控. 上述研究进展为OCORs在能源、环境和合成化学领域的应用奠定了坚实基础. 尽管OCORs在光催化领域前景广阔, 其发展仍面临如何精准光生电荷转移路径以提高OCORs的生成选择性、延长OCORs在反应体系中的寿命、拓展人工光合作用及环境修复等新应用体系, 以及实现催化剂的规模化制备与运行稳定性等多重挑战. 破解上述难题, 是深化自由基光化学认知、推动高效光催化体系应用的关键.
综上, 本文系统总结了OCORs的表征方法、合成策略、光催化应用及现存挑战, 以期引发研究人员的深入思考. 未来发展方向应聚焦于OCORs的精准生成与稳定性提升, 积极开拓人工光合作用与环境修复等新体系, 并攻克规模化制备难题, 加速其走向实际应用.

关键词: 氧中心有机自由基, 光催化, 过氧化氢, 二氧化碳还原, 污染物降解

Abstract:

In recent years, oxygen-centered organic radicals (OCORs) have garnered significant attention for their pivotal roles across diverse chemical and material science platforms. As a unique class of open-shell molecules, OCORs exhibit remarkable stability and highly tunable reactivity, enabling innovative possibilities for organic transformations and the design of advanced functional materials. Unlike conventional short-lived radicals, OCORs can maintain their stability for several months in complex environmental conditions while showcasing exceptional efficiency in catalytic processes. Their versatility extends to a range of applications, including environmental remediation, redox-active materials, and next-generation energy systems. This review provides a comprehensive summary of recent advancements in OCORs research, focusing on their characterization techniques, synthesis methods, and applications in electronic structure modulation and functional material design. Additionally, it highlights key challenges such as enhancing stability, selectivity, and scalability while proposing future research directions. These insights aim to foster deeper understanding and innovation, propelling the development of OCORs for broader scientific and industrial applications.

Key words: Oxygen-centered organic radicals, Photocatalysis, Hydrogen peroxide, Carbon dioxide reduction, Pollutant degradation

刘淑芳, 陈锋宇, 李思媛, 叶宇昕, 欧阳钢锋. 氧中心有机自由基最新研究进展: 表征、合成及应用[J]. 催化学报, 2026, 88: 183-206.

Shufang Liu, Fengyu Chen, Siyuan Li, Yu-Xin Ye, Gangfeng Ouyang. Recent advances in oxygen-centered organic radicals: Characterization, synthesis, and applications[J]. Chinese Journal of Catalysis, 2026, 88: 183-206.

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图/表 24

Fig. 1. (a) Chemical structures of CZAQ-1, CZAQ-2 and CZAQ-3. (b,c) EPR spectra of CzAQ-1 under Ar atmosphere before and after light irradiation, and the corresponding signal intensity variations. (d-f) EPR spectra of CzAQ-1 and CzAQ-2 under oxygen atmosphere with light irradiation. (g) Corresponding signal intensity variations. Reprinted with permission from Ref. [50]. Copyright 2024, Elsevier.

Fig. 2. (a) Mechanism diagram of competing electron transfer pathways in quinonoid structures. (b) The degradation efficiency of phenol using CZAQ-1 with different sacrificial agents under visible light of 10 mW·cm-2. Reprinted with permission from Ref. [50]. Copyright 2024, Elsevier.

Fig. 3. (a) The chemical structure of quinoid compounds. (b) O2 consumption and radical formation during reaction of 9,10-PQ with sulfur compounds. Dissolved oxygen was monitored by a meter in solutions of 5 μmol·L-1 9,10-PQ mixed with a series of reductants: Glutathione (GSH), Dithiothreitol (DTT), Na2S, Na2S2, Na2S3, and Na2S4. Reprinted with permission from Ref. [53]. Copyright 2019, American Chemical Society.

Fig. 4. (a) A Schematic depicts the formation process and resultant structure of GH-PDANSs. (b) Illustration of the initial dopamine autoxidation steps. (c) CV profiles of sample film-coated GCE obtained in a solution of 0.1 mol·L-1 Bu4NPF6 in acetonitrile as the supporting electrolyte at a scan rate of 0.1 V s-1. Reprinted with permission from Ref. [55]. Copyright 2022, Elsevier.

Fig. 5. (a) Initial steps of anthraquinone oxidation. (b) The structures and synthesis of TPC-3D, PYR-2D, and TPL-2D. (c) In-situ DRIFTS of light in argon and dark in oxygen process of TPC-3D. Reprinted with permission from Ref. [59]. Copyright 2024, Springer Nature.

Fig. 6. (a) The structures and synthesis of TPE-AQ and TPE-AC. (b) The odd-electron density in a single D-A unit of TPE-AQ through DFT calculation. Reprinted with permission from Ref. [27]. Copyright 2021, National Academy of Sciences.

Fig. 7. (a) Structure of aryl OCORs. (b) The composition of D-A type CPs, which have the potential to generate OCORs.

Fig. 8. (a) Synthesis of p-semiquinone-radical-bridged RE complexes 1 and 2. (b) Molecular structure of complex 1. All of the hydrogen atoms are omitted for clarity. Reprinted with permission from Ref. [68]. Copyright 2020, American Chemical Society.

Fig. 9. (a) The preparation of ECUT-AC and ECUT-AQ through Suzuki-Miyaura cross-coupling polycondensation. Reprinted with permission from Ref. [71]. Copyright 2022, Elsevier. (b) Synthetic routes of AQ-PAFs. (c) Photocatalytic H2O2 production by PAFs, building blocks, and photocatalytic H2O2 production by PAF-379 (d) using real water samples. Conditions: 50 mL water, photocatalyst (1 mg), air, λ > 420 nm, 300 W Xe lamp, 100 mW·cm-2. Reprinted with permission from Ref. [72]. Copyright 2025, John Wiley and Sons.

Fig. 10. (a) Synthetic routes of PQ-AB and FR-AB. Reprinted with permission from Ref. [78]. Copyright 2025, John Wiley and Sons. (b) Synthetic routes of P-PTAQ and O-PTAQ. (c) Temperature-dependent PL intensity of O-PTAQ (100-200 K). (d) Interconversion of charge-separated state (CS) and the lowest singlet excited state (S1) in common materials with positive exciton binding energy (Eb) and the required activation energy Ea (S1 → CS). (e) In O-PTAQ, the mutual transitions between CS and S1 involves a negative (Eb), with the activation energy (Ear) from CS to S1. Reprinted with permission from Ref. [79]. Copyright 2025, John Wiley and Sons.

Fig. 11. Illustration of the synthetic approach carried out for the synthesis of the tetratopic ligand via Buchwald-Hartwig amination reaction. Reprinted with permission from Ref. [81]. Copyright 2022, American Chemical Society.

Table 1 Comparison of photocatalytic H2O2 production performance between non-OCORs and OCORs-based photocatalysts a.

Catalyst	H₂O₂ yield (µmol·h^-1·g^-1)	AQY ^b	SCC ^c (%)	Conditions	Stability	Ref.
Nv-C≡N-CN	137	36.2% at 400 nm	0.23	O₂	5 cycles for 5 h	[94]
COF-N32	605	6.2 % at 469 nm	0.31	O₂	5 cycles for 60 h	[95]
COF-TfBpy	1042	8.1% at 420 nm	0.57	O₂	5 cycles for 40 h	[96]
CNW03	1889	8.53% at 420 nm	0.31	O₂	4 cycles for 4 h	[97]
2D-CTF	2412	16.8% at 420 nm	0.91	O₂	5 cycles for 10 h	[98]
DE7-M	2444	8.7% at 420 nm	0.28	O₂	5 cycles for 10 h	[99]
TTP	3132	7.61% at 420 nm	0.35	O₂	6 cycles for 6 h	[100]
CHF-DPDA	3450	16% at 420 nm	0.78	O₂	3 cycles for 18 h	[101]
SO₃H-COF	4971	15% at 400 nm	0.40	O₂	5 cycles for 4.17 h	[102]
TPB-COF-OH	6608	9.61% at 420 nm	0.84	O₂	12 h	[103]
TPT-alkynyl-AQ ^d	2368	25% at 365 nm	0.35	Air	5 cycles for 5 h	[28]
PAQ-TABPB	3351	6.36% at 400 nm	0.36	O₂	8 cycles for 32 h	[104]
PQ-AB	3400	5.2% at 400 nm	0.20	Air	5 cycles for 5 h	[78]
Sulfonyl-AQ	3849	25.9% at 420 nm	1.29	Air	5 cycles for 5 h	[105]
PAF-363	3930	5.32% at 420 nm	0.57	Air	10 cycles for 10 h	[106]
BCz-AQ	4007	25.9% at 470 nm	0.51	Air	10 cycles for 10 h	[107]
BTT-AQ	4218	8.60% at 420 nm	—	Air	46 h	[108]
Cz-AQ	4401	28.7% at 420 nm	1.25	Air	6 cycles for 10 h	[93]
TPC-3D	5940	30.9% at 420 nm	3.60	Air	5 cycles for 5 h	[59]
TPM-DADK	7210	46.2% at 405 nm	3.07	Air	5 cycles for 10 h	[109]

Fig. 13. (a) Synthesis of TPT-alkynyl-AQ, TPT-AQ, and TPT-imine-AQ. (b) Ambient H2O2 photosynthesis was conducted under natural sunlight, with water samples collected from diverse locations under recorded weather and temperature conditions. (c) Comparative H2O2 generation rates in various water matrices under ambient conditions. Reprinted with permission from Ref. [28]. Copyright 2022, National Academy of Sciences.

Table 2 Activity comparison between OCORs-based photocatalysts and other reported photocatalysts for photoredox methanation using H2O as the electron donor. a

Catalyst	Light conditions	CH₄ yield (µmol·h^-1·g^-1)	CH₄ selectivity (%)	Ref.
PeTt-POP	100 W Xe lamp	0.034	100	[113]
Ru@TiMOF-10-NH₂(I)	300 W Xe lamp full spectrum	2.5	10.8	[114]
Pt/TiO₂-SiO₂	300 W Xe lamp (420-780 nm)	9.7	39.8	[115]
Bi₂MoO₆	300 W Xe lamp full spectrum	12.4	44.6	[116]
KBH-C₃N₄	300 W Xe lamp full spectrum	5.93	88.2	[117]
Ni₅-CN	300 W Xe lamp full spectrum	0.5	18.9	[118]
Au/Cd_1-xS	600 mW·cm^-2 (200-800 nm)	11.3	22	[119]
TPA-DPA PPK	100 W Xe lamp with an AM 1.5G filter	0.043	98	[120]
Cu-SA-CO	300 W Xe lamp (400-750 nm)	58.5	100	[121]
TPA-PQ ^b	300 W Xe lamp (400-750 nm)	2150	97	[122]
TPE-PT	300 W Xe lamp full spectrum	10.6	90	[29]

Fig. 14. (a) Molecular structures of TPE-PT, TPE-AQ, and TPT-AQ, along with (b) the photocatalytic CO2 reduction performance evaluated in a gas-solid reactor under CO2 and water vapor at room temperature for 4 h, without adding any photosensitizer or sacrificial agent. (c) Cycling stability of TPE-PT for photocatalytic CO2 reduction over five consecutive runs. (d) Schematic illustrating the high electronic selectivity of TPE-PT for CH4 using only CO2 and H2O. Reprinted with permission from Ref. [29]. Copyright 2023, John Wiley and Sons.

Table 3 Photocatalytic activity and light intensity between OCORs-based photocatalysts and other reported photocatalysts for micropollutants degradation. a

Catalyst	Condition	Light conditions (mW·cm^-2)	Adsorption time (min)	Reaction time (min)	Degradation rate (%)	Ref.
WUCN-500	0.2 g·L^-1 Cat, 0.28 mmol·L^-1 (OA)	350 (320 < λ < 800 nm)	30	30	43	[127]
ACN0.5	0.5 g·L^-1 Cat, 0.01 mmol·L^-1 (MB)	38 (λ > 400 nm)	60	300	100	[128]
LZS	0.2 g·L^-1 Cat, 0.15 mmol·L^-1 (4-CP)	326 (320 < λ < 780 nm)	30	10	100	[129]
Cs₂AgBiBr₆	2.0 g·L^-1 Cat, 0.20 mmol·L^-1 (RhB)	33 (λ > 420 nm)	60	120	20	[130]
G_THS	0.125 g·L^-1 Cat, 0.02 mmol·L^-1 (CIP)	135 (AM 1.5G)	60	360	82	[131]
g-C₃N₄	0.5 g·L^-1 Cat, 0.09 mmol·L^-1 (BPA)	180 (300 W Xenon lamp)	30	60	35	[132]
COF-TD1	0.3 g·L^-1 Cat, 0.02 mmol·L^-1 (BPA)	125 (λ > 420 nm)	30	120	97	[133]
TPE-AQ	0.05 g·L^-1 Cat, 0.002 mmol·L^-1 (BPA)	2.0 (λ > 400 nm)	60	60	92	[134]

Fig. 15. Comparison of traditional transient ROS (a) and long-lived OCORs (b). (c) Synthetic routes to TPE-AQ and TPE-FN. (d) Photocatalytic activity of TPE-AQ across varying light intensities. (e) Degradation of BPA by TPE-AQ in diverse natural water matrices. Reprinted with permission from Ref. [134]. Copyright 2025, Royal Society of Chemistry.

Table 4 Comparison of mineralization for organic pollutants between OCORs-based photocatalysts and other reported photocatalysts. a

Photocatalyst	Light condition	Organic pollutant	Dosage (g·L^-1)	H₂O₂ activation	TOC removal ^b	Ref.
OPCN	λ > 400 nm 100 mW·cm^-2	5 mg·L^-1 phenol	0.5	O₂; FeCl₃·6H₂O (0.4 g·L^-1)	26.09% (60 min)	[138]
Fe/RF	λ > 420 nm 35.2 mW·cm^-2	50 mg·L^-1 phenol	0.4	—	68% (150 min)	[139]
Coral-B-CN	AM 1.5G	20 mg·L^-1 4-chlorophenol	0.4	O₂; FeSO₄·7H₂O (0.02 g·L^-1)	70.30% (50 min)	[140]
C≡N-CN/IS/Ppy	λ > 420 nm 140 mW·cm^-2	10 mg·L^-1 metronidazole	1	O₂; FeSO₄·7H₂O (0.08 g·L^-1)	59.10% (120 min)	[141]
CdS/rGO	λ > 420 nm; ULI ^c	10 mg·L^-1 phenol	1	O₂; FeSO₄·7H₂O (0.5 g·L^-1)	43.66% (60 min)	[142]
BCz-AQ	λ > 400 nm 100 mW·cm^-2	10 mg·L^-1 phenol	0.1	Air; K-FeOCl (Heteroogeneous); 0.1 g·L^-1)	94% (90 min)	[107]

Fig. 16. (a) The molecular structure of building blocks, BCZ-AQ, and CZ-AQ. (b) Comparison of TOC removal between BCZ-AQ and CZ-AQ. (c) Degradation performance under low light intensity (inset: TOC removal efficiency). (d) Reaction mechanism illustrating simultaneous micropollutant mineralization and H2O2 generation in UHSFP. Reprinted with permission from Ref. [107]. Copyright 2024, John Wiley and Sons.

Table 5 Activity comparison for disinfection between OCORs-based photocatalysts and other reported photocatalysts a.

Photocatalyst	Light condition	Initial concentration of bacterial	Reaction time for complete disinfection	Ref.
Cu-MoS₂	100 mW·cm^-2 (Xeon lamp, AM 1.5G)	5 log	20 min (E. coli ^b)	[161]
CeO₂/PCN	100 mW·cm^-2 (λ ≥ 420 nm)	5 log	120 min (S. aureus ^c)	[162]
FeSO₄/H₂O₂	120 mW·cm^-2 (Xeon lamp)	6 log	4 h (E. coli)	[163]
PEI/C₃N₄	150 mW·cm^-2 (AM 1.5G)	6.2 log	45 min (E. coli)	[164]
SA-SADF-H⁺	100 mW·cm^-2 (λ > 420 nm)	8 log	98.6% in 1.5 h (E. coli)	[165]
C₃N₄/PDINH	100 mW·cm^-2 (AM 1.5G)	4 log	40 min (S. aureus)	[166]
Cz-AQ	100 mW·cm^-2 (Xeon lamp, λ > 420 nm)	5 log	10 min (E. coli)	[60]
PF-Cz-AQ	100 mW·cm^-2 (Xeon lamp, λ > 420 nm)	5 log	15 min (E. coli)	[60]

Fig. 17. (a) Structures and synthesis of Cz-AQ, Cz-ANT and Cz-PHE. The PF-Cz-AQ film was prepared by electrospinning the mixed solution of Cz-AQ and PS. (b) Photograph of the on-site experimental setup. (c,d) Plate count agar results of water samples before and after 40 min treatment. (e) Schematic comparison of action modes between conventional short-lived ROS and OCORs. Reprinted with permission from Ref. [60]. Copyright 2025, Springer Nature.

Fig. 18. (a) Photocatalytic selective oxidation of C(sp3)-H bonds in hydrocarbons. (b) The BAL yields and selectivity of C(sp3)-H photooxidation reaction were evaluated using different halogen acids in CH3CN. (c) The formation rate of BAL and selectivity toward aldehydes were measured at different concentration of HBr in CH3CN. (d) Proposed reaction mechanism for the photoinduced aerobic oxidation of toluene in CH3CN. Reprinted with permission from Ref. [188]. Copyright 2026, American Chemical Society.

Fig. 19. Schematic illustration for the applications of OCORs in photocatalysis.

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氧中心有机自由基最新研究进展: 表征、合成及应用

Recent advances in oxygen-centered organic radicals: Characterization, synthesis, and applications

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