光催化分解水与有机合成制氢: 大评述

doi:10.1016/S1872-2067(24)60216-0

催化学报 ›› 2025, Vol. 70: 44-114.DOI: 10.1016/S1872-2067(24)60216-0

光催化分解水与有机合成制氢: 大评述

Oleksandr Savateev^a^,^*(), 庄镜儒^a, 万思杰^b, 宋春山^a, 曹少文^b^,^*(), Tang Junwang^c^,^*()

^a香港中文大学化学系, 香港新界
^b武汉理工大学材料合成与加工先进技术国家重点实验室, 湖北武汉 430070
^c清华大学化学工程系, 工业催化中心, 北京 100084

收稿日期:2024-10-02 接受日期:2024-11-27 出版日期:2025-03-18 发布日期:2025-03-20
通讯作者: * 电子信箱: oleksandrsavatieiev@cuhk.edu.hk (O. Savateev),swcao@whut.edu.cn (曹少文),jwtang@tsinghua.edu.cn (Tang Junwang).
基金资助:
香港中文大学研究委员会(Direct Grant 476208494)

Photocatalytic water splitting versus H₂ generation coupled with organic synthesis: A large critical review

Oleksandr Savateev^a^,^*(), Jingru Zhuang^a, Sijie Wan^b, Chunshan Song^a, Shaowen Cao^b^,^*(), Junwang Tang^c^,^*()

^aDepartment of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China
^bState Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, Hubei, China
^cIndustrial Catalysis Center, Department of Chemical Engineering, Tsinghua University, Beijing 100084, China

Received:2024-10-02 Accepted:2024-11-27 Online:2025-03-18 Published:2025-03-20
Contact: * E-mail: oleksandrsavatieiev@cuhk.edu.hk (O. Savateev),swcao@whut.edu.cn (S. Cao),jwtang@tsinghua.edu.cn (J. Tang).
About author:Oleksandr Savateev (The Chinese University of Hong Kong) received his BSc and MSc degrees in chemistry from the National Technical University of Ukraine “Kyiv Polytechnic Institute” and the PhD degree in organic chemistry from the Institute of Organic Chemistry of the National Academy of Science of Ukraine. In 2015, as a postdoctoral researcher he joined the Max Planck Institute of Colloids and Interfaces in Potsdam, Germany. In 2017, at the same institute, he started his group “Innovative Heterogeneous Photocatalysis”. In 2023, he took the position of the Vice-Chancellor Associate Professor at the Chinese University of Hong Kong. His current research interests include organic synthesis mediated by heterogeneous photocatalysts, application of photocharged semiconductors in organic synthesis and data-driven research. He is an editor and author of several books, including “Carbon nitrides. Structure, properties and applications in science and technology”, and author of more than 100 research articles. In 2024, he completed his Habilitation in Organic Chemistry at the University of Potsdam, Germany.
Shaowen Cao (State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology) was appointed as the young member of the Editorial Board of Chinese Journal of Catalysis in 2017. Professor Shaowen Cao received his B.S. in Geochemistry in 2005 from the University of Science and Technology of China, and his Ph.D. in Materials Chemistry & Physics in 2010 from the Shanghai Institute of Ceramics, Chinese Academy of Sciences. He then worked as a Research Fellow at the School of Materials Science and Engineering, Nanyang Technological University until Feb 2014. He is now a Professor at State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology. From Mar 2018 to Feb 2020, he was a Visiting Scientist at Max Planck Institute of Colloids and Interfaces. His current research interests include the design and fabrication of photocatalytic materials for energy and environmental applications. He is the author or co-author of more than 150 peer-reviewed scientific papers., with over 22000 citations, an H-index 70 and 26 ESI highly cited papers. He is also one of the “Highly Cited Researchers” from 2018 to 2024 awarded by Clarivate Analytics.
Junwang Tang is a Member of Academia Europaea, a Leverhulme Trust Senior Research Fellow, Fellow of RSC and Fellow of European Academy of Sciences and formerly a full Professor at Chemical Engineering in University College London. He is currently a Chair Professor of Materials Chemistry and Catalysis in the Department of Chemical Engineering and Director of the Industrial Catalysis Centre at Tsinghua University. He has pioneered in photon-phonon co-driven catalysis, alongside with photocatalysis, for the activation of small molecules (e.g., H₂O, CO₂, CH₄, and N₂), and microwave catalytic depolymerisation of plastics. He has received many prestigious honours, including the 2022 IChemE Oil and Gas Award, the 2021 IChemE Andrew Medal, the 2021 RSC Corday-Morgan Prize, and the 2021 IChemE Innovative Product Award. He is also the Editor or Associate Editor of four journals, including Appl. Catal. B, EES Solar, Carbon Future and Chin. J. Catal.

摘要/Abstract

摘要：

利用自然太阳光进行光催化水分解被认为是一种可持续的生产H₂和O₂方法. 虽然H₂具有很高的市场价值, 但水分解的副产品O₂的价值较低. 为了使光催化制氢在经济性上优于甲烷制氢, 研究者通常将氢气的生成与高附加值有机物的合成相结合进行研究. 本文对20世纪80年代以来发展起来的脱氢反应进行了批判性总结和分析, 对光催化脱氢反应进行了系统性分类, 并将结果收录于在线数据库中. 该数据库对均相和非均相光催化剂在脱氢反应中的性能(如分析及制备规模下有机物的产率及量子效率)进行了比较, 指出了现有方法和光催化系统的局限, 并展望了未来的发展方向.

关键词: 少电子受体的脱氢, 光催化, 光氧化还原催化, 氢气, 有机合成

Abstract:

Photocatalytic water splitting using natural solar light is considered as a sustainable approach to generate H₂ and O₂. While H₂ has high market value, the by-product of water splitting, oxygen, is less valuable. To make H₂ produced by means of photocatalysis more economically competitive to that generated from methane, its generation is studied together with synthesis of organic compounds that have higher market value. This review summarizes and analyzes critically dehydrogenation reactions that were developed since 1980s. Photocatalytic dehydrogenation reactions are classified and the results are collected in the online database. Performance of homogeneous and heterogenous photocatalysts in dehydrogenation reactions, such as yield rates of organic products on analytical and preparative scales, and quantum efficiencies are compared. Current limitations of the existing methods and photocatalytic systems are identified and directions for the future developments are outlined.

Key words: Acceptorless dehydrogenation, Photocatalysis, Photoredox catalysis, Hydrogen, Organic synthesis

Oleksandr Savateev, 庄镜儒, 万思杰, 宋春山, 曹少文, Tang Junwang. 光催化分解水与有机合成制氢: 大评述[J]. 催化学报, 2025, 70: 44-114.

Oleksandr Savateev, Jingru Zhuang, Sijie Wan, Chunshan Song, Shaowen Cao, Junwang Tang. Photocatalytic water splitting versus H₂ generation coupled with organic synthesis: A large critical review[J]. Chinese Journal of Catalysis, 2025, 70: 44-114.

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图/表 129

Table 1 Thermodynamics of water splitting into H2 and O2, and dehydrogenation of organic compounds under solar radiation.

Entry	ΔG^{0 a} (kJ mol^‒1)	E_g^b (eV)	η_max^c (%)
1	237	1.23	27 (N_p = 2)
2	474	1.23	14 (N_p = 4)
3	63	0.33	50 (N_p = 2)
4	53	0.27	50 (N_p = 2)
5	18	0.09	50 (N_p = 2)
6	27	0.14	50 (N_p = 2)
7	40	0.10	25 (N_p = 4)
8	79	0.14	17 (N_p = 6)
9	78	0.4	48 (N_p = 2)
10	150	0.39	24 (N_p = 4)
11	98 [7]	0.17	17 (N_p = 6)
12	60 [8]	0.31	50 (N_p = 2)
13	93 [9]	0.48	48 (N_p = 2)
14	19 [10]	0.10	50 (N_p = 2)
15	69 [11]	0.36	49 (N_p = 2)
16	434 [12]	0.25	6 (N_p = 18)
17	41 [13]	0.21	50 (N_p = 2)

Fig. 1. Illustration of the efficiency of solar photons utilization in photocatalytic water splitting and dehydrogenation of organic compounds. (A) Terrestrial (air mass 1.5) flux of solar photons (I) as a function of wavelength is calculated using data from Ref. [17] according to the equation: I = (P × λ)/(h × c × NA), where P - distribution of power, W m-2 nm-1. λ - wavelength of incident photon, m. h - Planck constant, 6.63 × 10-34 m2 kg s-1. c - speed of light in vacuum, 3 × 108 m s-1. NA - Avogadro number, 6.02 × 1023 mol-1. (B) Dependence of the efficiency of solar photons utilization as a function of semiconductor energy gap (Eg) for reactions involving different number of photons (Np).

Fig. 2. The number of articles vs. the publication year and the number of entries vs. the publication year that are included in the database [19].

Fig. 3. A general reaction mechanism. (A) Thermodynamic aspects of dehydrogenation reaction. (B) No. of entries in the database [19] vs. the energy of incident photon used in the corresponding photocatalytic experiment. (C) Reductive quenching of the photocatalyst excited state. (D) Oxidative quenching of the photocatalyst excited state.

Fig. 4. Overview of chemical structures of photocatalysts that are based on transition metals. (A) These structures act both as a photocatalyst and H2-evolution catalyst - typically photocatalytic dehydrogenation reactions do not require any additional H2-evolution catalyst. (B) These structures act as a photocatalyst - typically photocatalytic dehydrogenation reactions mediated by these systems require some H2-evolution catalyst.

Fig. 5. Overview of chemical structures of transition metal free photocatalysts.

Fig. 6. Classification of the photocatalysts [19]. (A) Homogeneous vs. heterogeneous photocatalysis. (B-D) Classification of the photocatalysts based on their chemical composition. (E) Commercial photocatalysts vs. custom made. (F) Assembly of a photocatalyst and H2-evolution catalyst.

Fig. 7. Overview of hybrid systems composed of a sensitizer and H2-evolution catalyst. (A) Chemical structure of Cobaloxime-4CzIPN. (B) Chemical structure of a secondary building unit of Hf12-Ru-Co. Red spheres represent O atoms, cyan spheres - Hf atoms, violet spheres - C atoms, bpy - 2,2’-bipyridine.

Fig. 8. Schematic structures of some of the common photocatalysts’ electronically-excited states. (A) *[Ru(bpy)3]2+. (B) Pt(II) terpyridyl complex. See Fig. 4A for structure of Ar and R. (C) Local chemical structure of CdSe (wurtzite) ground state, electronically-excited state and a photocatalytic cross-coupling cycle that shows temporary storage of radicals and H-atoms on CdSe surface. (D) Local chemical structure of *ZnO (wurtzite) and *TiO2 (anatase) electronically-excited states. (E-I) Chemical structures of *[W10O32]4?, *GaN, *[Mes-Acr-Me], 4CzIPN, *Eosin Y electronically-excited states.

Fig. 9. Graphitic carbon nitrides. (A) Structure of melon-type g-CN and cyanamide-functionalized g-CN (NCN-CNx). (B) A structure of melon-type *g-CN electronically-excited state. Adapted with permission from Ref. [189], John Wiley & Sons.

Fig. 10. Overview of chemical structures of H2-evolution catalysts. Co(dmgH)(dmgH2)Cl and Co(dmgH)2Cl2 represent the same structure.

Fig. 11. Classification of H2-evolution catalysts [19]. (A) Homogeneous vs. heterogeneous H2-evolution catalysts. (B-D) Classification of the H2-evolution catalysts based on their chemical composition. (E) Custom made refers to H2-evolution catalysts, which were prepared in the corresponding reference. Commercial - H2-evolution catalysts, which are available for purchase. (F) Combination of the photocatalyst and H2-evolution catalyst.

Fig. 12. Modes of H2-evolution catalysts operation illustrated on cobaloximes. (A,B) Electronically excited Co-species are not involved. (C) Excitation of Co-species with light triggers β-hydride elimination. (D) Cobaloxime acts as the photocatalyst and H2-evolution catalyst.

Fig. 13. Performance of homogeneous and heterogeneous systems in photocatalytic dehydrogenation reactions based on the database analysis in double logarithmic scale [19]. Black squares represent heterogeneous catalysts, blue circles - homogeneous catalysts. Arrows highlight datapoints discussed in the main text. (A) Major organic product yield vs. substrate loading. (B) Productivity of the photocatalytic system that is composed of photocatalyst, H2-evolution catalyst and auxiliary agents (acid, base, HAT-catalyst, etc.) vs. loading of the substrate. (C) Correlation between H2 yield vs. the yield of the major organic product. The line represents 1:1 ratio between H2 and the organic product. Only data derived from the same experiment are plotted. (D) Productivity of catalysts vs. the AQY of H2 or organic product. Division into homogeneous and heterogeneous was made based on the type of the photocatalysts.

Fig. 14. Classification of dehydrogenation reactions [19]. (A) Based on the reaction type. (B) Based on the extent of desaturation. (C) Meta analysis of the database [19]. In “Atoms involved in bond formation” 12 entries are duplicated in categories C?N and C?C.

Fig. 15. Legend to reaction schemes. [By-product(s)] denotes compounds that are formed in stoichiometric quantities with the respect to the major organic product.

Fig. 16. A single example of photocatalytic C?B bond formation coupled with H2 evolution.

Fig. 17. Synthesis of substituted naphthalenes that is accompanied by H2 evolution.

Fig. 18. Photocatalytic alkenylation of electron rich arenes.

Fig. 19. Decarboxylative coupling of α-imino-oxy acids with styrenes.

Fig. 20. Synthesis of 1,2-dihydro-1-arylnaphthalenes upon dimerization of styrene and its derivatives.

Fig. 21. Synthesis of benzosultams.

Fig. 22. Synthesis of indoles from enamines.

Fig. 23. Cyanomethylation of benzene over Pd/TiO2.

Fig. 24. Coupling of benzene and cyclohexane.

Fig. 25. Coupling of diethylether with benzene.

Fig. 26. Coupling of aromatic compounds with THF.

Fig. 27. Coupling of alkylarenes with aldehydes.

Fig. 28. Coupling of N-aryltetrahydroisoquinolines with indoles using graphene-supported RuO2 and Eosin Y.

Fig. 29. Coupling of N-aryltetrahydroisoquinolines with indoles using Eosin Y and Co(dmgH)2Cl2.

Fig. 30. Coupling of THF with isoquinoline.

Fig. 31. Coupling of alkyltrifluoroborates with electron-deficient heterocycles.

Fig. 32. Coupling of hydrocarbons with electron-deficient heterocycles.

Fig. 33. Coupling of alkanes with alkenes.

Fig. 34. Coupling of isobutane with quinoline derivative.

Fig. 35. Decarboxylative coupling of carboxylic acids with alkenes.

Fig. 36. Decarboxylative coupling of adamantane carboxylic acid with benzothiazole.

Fig. 37. Trifluoromethylation of aromatic compounds with trifluoroacetic acid.

Fig. 38. α-allylation of aldehydes.

Fig. 39. Synthesis of phenanthrene derivatives.

Fig. 40. Synthesis of phenanthrene derivatives using Co(dmgH)2PyCl as the photocatalyst.

Fig. 41. Desaturation of amides.

Fig. 42. Desaturation of piperidione derivative.

Fig. 43. Dehydrogenation of various substrates.

Fig. 44. Dehydrogenation of various organic compounds using [nBu4N]4[W10O32].

Fig. 45. Desaturation of alkanes by IrH2(CF3CO2)(PCy3)2, L = PCy3.

Fig. 46. Desaturation of cyclohexane by RhClCO(PMe3)2.

Fig. 47. Aromatization of 1-phenyl tetrahydroisoquinoline.

Fig. 48. Aromatization of 1,2,3,4-tetrahydronaphthalene.

Fig. 49. Synthesis of pyrazoles from pyrazolines.

Fig. 50. Dehydrogenation of N-containing heterocycles.

Fig. 51. Dehydrogenation of 2,5-dihydropyrroles.

Fig. 52. Synthesis of unsaturated ketones upon ring opening of cyclohexanols.

Fig. 53. Synthesis of unsaturated ketones upon ring opening of cyclohexanols.

Fig. 54. Synthesis of alkenes from carboxylic acids.

Fig. 55. Synthesis of enamines from aminoacids.

Fig. 56. Synthesis of alkenes from triglycerides employing biocatalytic/photocatalytic cascade.

Fig. 57. Dehydroformylation of carbonyl compounds.

Fig. 58. Dehydroformylation of benzylic alcohols employing [nBu4N]4[W10O32] and Co(dmgH)2PyCl.

Fig. 59. Dehydroformylation of benzylic alcohols employing [ToMRh(CO)2].

Fig. 60. Coupling of THF with cyclohexane.

Fig. 61. Coupling of THF with tertiary amines.

Fig. 62. Coupling of toluene with acetone.

Fig. 63. Cycanomethylation of cyclohexane.

Fig. 64. Alkylation and arylation of allylic C?H bonds.

Fig. 65. Coupling of ketones with alkenes.

Fig. 66. Coupling of glycine derivatives with C-nucleophiles.

Fig. 67. Coupling of isochromans with β-ketoesters.

Fig. 68. Non-oxidative methane coupling. (A) Chemical structure of NBOHC and a scheme of a mechanism of C?H bond cleavage in methane. (B) SiO2 modified with metals. (C) Non-oxidative methane coupling on CeO2.

Fig. 69. TEM image of TiO2-SiO2 hierarchical macro-mesoporous structure and representation of the ideal structure.

Fig. 70. Sequential two-photon excitation of Zn(II)-ZSM-5-.

Fig. 71. SEM and TEM images of GaN nanowires, and a scheme of a mechanism of benzene synthesis from methane.

Fig. 72. Dimerization of dioxane over ZnS.

Fig. 73. Photocatalytic conversion of triethylamine and diethylamine. H2-cat. denotes H2-evolution catalyst. In this example, a photocatalyst (PC) and H2-evolution catalyst are represented by the same material - ZnS.

Fig. 74. Dimerization of 2,5-dihydrofuran over ZnS.

Fig. 75. Dimerization of acetone and tert-butanol.

Fig. 76. Oligomerization of methylfurans over ZnIn2S4:Ru.

Fig. 77. Photocatalytic conversion of alcohols.

Fig. 78. Dehydrogenation of alcohols mediated by CdSe nanoparticles.

Fig. 79. Synthesis of lactones from vicinal diols.

Fig. 80. Sorption of alcohol at SrTiO3:Fe O-vacancies.

Fig. 81. TEM image of the hybrid material featuring the core made of Au-Pt and the loose shell - CdS.

Fig. 82. SEM image featuring CdS nanoparticles that were grown on Ti3C2Tx sheets.

Fig. 83. Scheme of a mechanism of benzyl alcohol conversion into benzaldehyde, benzoin and deoxybenzoin.

Fig. 84. Synthesis of hydrobenzoin from benzylalcohol.

Fig. 85. Dehydrogenation of benzylic alcohols and synthesis of hydrobenzoin, and benzoin.

Fig. 86. Synthesis of hydroxyacetaldehyde dimer from glycerol over TiO2 rutile (110) facet.

Fig. 87. Dehydrogenation of alcohols and pinacol coupling over [Me2(C16H33)2N]4[Pt2(pop-BF2)4].

Fig. 88. Dehydrogenation of alcohols employing Ni(NTf2)2/[Mes-Acr-Me]ClO4/Thiophosphoric acid.

Fig. 89. Ethanol conversion into 1,1-diethoxyethane and butane-2,3-diol.

Fig. 90. Synthesis of amides from hemiaminals employing (N,N)-bidentate Mn(I) complex.

Fig. 91. Coupling of alkenes with O- and N-nucleophiles.

Fig. 92. Coupling of aromatic hydrocarbons with alcohols.

Fig. 93. Lactonization of 2-aryl benzoic acids. Two pathways are shown.

Fig. 94. Synthesis of ketones from alkenes against Markovnikov’s rule.

Fig. 95. Scheme of the mechanism of aniline synthesis from benzene and ammonia.

Fig. 96. Synthesis of phenol and N-Boc-protected aniline from benzene and water, or BocNH2 (tert-butyl carbamate).

Fig. 97. Coupling of aromatic hydrocarbons with primary amines.

Fig. 98. N-arylation of azoles.

Fig. 99. Coupling of pyrazole with heterocycles.

Fig. 100. N-arylation of NH-sulfoximines.

Fig. 101. Annulation of imines with alkynes.

Fig. 102. Synthesis of oxazolines.

Fig. 103. Intramolecular cyclization of α-imino-oxy acids.

Fig. 104. Pathways of primary amines oxidation.

Fig. 105. Synthesis of tri- and tetra-substituted imidazoles from benzylic amines.

Fig. 106. XPS spectra of Ni/CdS only (Fresh), Ni/CdS in the presence of dibenzylamine in the dark (+ BA) and Ni/CdS in the presence of dibenzylamine exposed to light (+ Light).

Fig. 107. Dehydrogenation of tetrahydroisoquinolines.

Fig. 108. Coupling and dehydrogenation of tetrahydroisoquinolines.

Fig. 109. Synthesis of substituted anilines via dehydrogenation of enamines.

Fig. 110. Synthesis of 3,4-dihydroisoquinoline from 1,2,3,4-tetrahydroisoquinoline.

Fig. 111. A chemical structure of a sensitizer (photocatalyst).

Fig. 112. Synthesis of benzimidazoles.

Fig. 113. Dehydrogenation of Hantzsch ester.

Fig. 114. A photocatalytic version of Arbuzov reaction employing triethylphosphite and an aromatic hydrocarbon.

Fig. 115. Phosphinoylation of thiazoles.

Fig. 116. Synthesis of benzophospholes.

Fig. 117. Phosphinolylation of enamines and enamides.

Fig. 118. Synthesis of various phosphorylated heterocycles.

Fig. 119. Phosphinoylation of 2-methylfuran and other heterocycles.

Fig. 120. Coupling of N,N-dialkylaniline with trialkylphosphite.

Fig. 121. Sulfonylation of α-methylstyrene derivatives.

Fig. 122. Synthesis of benzothiazoles synthesis from thiobenzanilides.

Fig. 123. Coupling of thiols with allylic hydrocarbons.

Fig. 124. Silylation of alkenes.

Fig. 125. Dealkylation of N-substituted anilines.

Fig. 126. Synthesis of silyl ethers and silanols.

Fig. 127. Synthesis of disulfides from thiols employing CpMn(CO)3.

Fig. 128. Synthesis of disulfides from thiols employing Mn(CO)5Br.

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光催化分解水与有机合成制氢: 大评述

Photocatalytic water splitting versus H₂ generation coupled with organic synthesis: A large critical review

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光催化分解水与有机合成制氢: 大评述

Photocatalytic water splitting versus H2 generation coupled with organic synthesis: A large critical review

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Photocatalytic water splitting versus H₂ generation coupled with organic synthesis: A large critical review