Application of metal-porphyrin-based frameworks in photocatalysis

doi:10.11949/0438-1157.20200472

Abstract

Abstract:

Metal-organic frameworks (MOFs) are organic-inorganic hybrid porous crystalline materials formed by metal ions or metal clusters and polydentate organic ligands connected by coordination bonds, with a large specific surface area and holes, and the structure is also easy to achieve tailoring. What??s more due to a broad absorption covering nearly all the visible light region, porphyrins can be used as organic linkers to expand the spectral response range of MOFs. Therefore, porphyrin-based MOF materials are widely used in the field of photocatalysis. This paper is to review the applications of metal-porphyrin-based framework materials in photocatalytic hydrogen evolution, oxygen evolution, reduction of CO₂, degradation of organic pollutants and photocatalytic selective organic synthesis. In addition, the development of metal-porphyrin-based framework materials in the field of photocatalysis is prospected.

Key words: MOFs, porphyrin, corrole, photocatalysis

摘要：

金属-有机框架(metal-organic frameworks，MOFs)是一种由金属离子或金属簇与多齿有机配体通过配位键连接而形成的有机无机杂化多孔晶态材料，具有较大的比表面积和孔道，同时结构也易于实现剪裁。近十几年MOFs在催化、气体吸附等领域得到了较大发展。卟啉等四吡咯大环结构有很好的光吸收特性，作为连接体应用于MOFs中可有效拓宽其吸收光谱，因此，基于卟啉配体的MOFs被广泛应用于光催化领域。本文综述了近十年来金属-卟啉框架材料在光催化选择性有机合成、析氢、析氧、还原CO₂、降解有机污染物方面的应用，同时对金属-卟啉框架材料未来在光催化领域的发展进行了展望。

关键词: 金属有机框架, 卟啉, 咔咯, 光催化

CLC Number:

O 644.1

Meng JIA, Jiabin ZHANG, Yaqing FENG, Bao ZHANG. Application of metal-porphyrin-based frameworks in photocatalysis[J]. CIESC Journal, 2020, 71(9): 4046-4057.

贾勐, 张嘉宾, 冯亚青, 张宝. 金属-卟啉框架材料在光催化领域的应用[J]. 化工学报, 2020, 71(9): 4046-4057.

References 76

1	Demessence A, Long J R. Selective gas adsorption in the flexible metal-organic frameworks Cu(BDTri)L (L=DMF, DEF)[J]. Chemistry, 2010, 16(20): 5902-5908.
2	Li J R, Kuppler R J, Zhou H C. Selective gas adsorption and separation in metal-organic frameworks[J]. Chem. Soc. Rev., 2009, 38(5): 1477-1504.
3	Murray L J, Dinca M, Long J R. Hydrogen storage in metal-organic frameworks[J]. Chem. Soc. Rev., 2009, 38(5): 1294-1314.
4	Lismont M, Dreesen L, Wuttke S. Metal-organic framework nanoparticles in photodynamic therapy: current status and perspectives[J]. Advanced Functional Materials, 2017, 27(14): 1606314-1606329.
5	Wu C D, Hu A G, Zhang L, et al. A homochiral porous metal-organic framework for highly enantioselective heterogeneous asymmetric catalysis[J]. J. Am. Chem. Soc., 2005, 127(25): 8940-8941.
6	Dong B X, Qian S L, Bu F Y, et al. Electrochemical reduction of CO₂ to CO by a heterogeneous catalyst of Fe-porphyrin-based metal-organic framework[J]. ACS Applied Energy Materials, 2018, 1(9): 4662-4669.
7	Wang L, Jin P, Duan S, et al. In-situ incorporation of copper(II) porphyrin functionalized zirconium MOF and TiO₂ for efficient photocatalytic CO₂ reduction[J]. Science Bulletin, 2019, 64(13): 926-933.
8	Deria P, Gomez D A, Hod I, et al. Framework-topology-dependent catalytic activity of zirconium-based (porphinato) zinc(Ⅱ) MOFs[J]. Journal of the American Chemical Society, 2016, 138(43): 14449-14457.
9	Liang J, Xie Y Q, Wu Q, et al. Zinc porphyrin/imidazolium integrated multivariate zirconium metal–organic frameworks for transformation of CO₂ into cyclic carbonates[J]. Inorganic Chemistry, 2018, 57(5): 2584-2593.
10	Morris W, Volosskiy B, Demir S, et al. Synthesis, structure, and metalation of two new highly porous zirconium metal-organic frameworks[J]. Inorganic Chemistry, 2012, 51(12): 6443-6445.
11	Sharma N, Dhankhar S S, Kumar S, et al. Rational design of a 3D Mn^II‐metal-organic framework based on a nonmetallated porphyrin linker for selective capture of CO₂ and one-pot synthesis of styrene carbonates[J]. Chemistry-A European Journal, 2018, 24(62): 16662-16669.
12	Dhakshinamoorthy A, Li Z, Garcia H. Catalysis and photocatalysis by metal organic frameworks[J]. Chemical Society Reviews, 2018, 47(22): 8134-8172.
13	Deng X, Li Z, García H. Visible light induced organic transformations using metal-organic-frameworks (MOFs)[J]. Chemistry-A European Journal, 2017, 23(47): 11189-11209.
14	Chen Y, Wang D, Deng X, et al. Metal-organic frameworks (MOFs) for photocatalytic CO₂ reduction[J]. Catalysis Science & Technology, 2017, 7(21): 4893-4904.
15	安阳. 系列金属有机骨架材料的设计、制备及光催化分解水性能的研究[D]. 济南: 山东大学, 2019.
	An Y. Study on structural design, preparation and photocatalytic water splitting property of series of metal-organic framework materials[D]. Jinan: Shandong University, 2019.
16	Jiang H L, Makal T A, Zhou H C. Interpenetration control in metal-organic frameworks for functional applications [J]. Coordination Chemistry Reviews, 2013, 257(15/16): 2232-2249.
17	袁履冰, 张田林. 卟啉化合物的共振能[J]. 有机化学, 1986, 4: 289-290.
	Yuan L B, Zhang T L. Resonance energy of porphyrins[J]. Chinese Journal of Organic Chemistry, 1986, 4: 289-290.
18	Zhang L, Yuan S, Feng L, et al. Pore‐environment engineering with multiple metal sites in rare-earth porphyrinic metal-organic frameworks[J]. Angewandte Chemie International Edition, 2018, 57(18): 5095-5099.
19	刘兴燕, 徐永港, 熊成, 等. 卟啉金属有机骨架材料在光催化领域的研究进展[J]. 应用化工, 2019, 48(2): 482-485.
	Liu X Y, Xu Y C, Xiong C, et al. Recent progress on the photocatalysis of porphyrin-based metal-organic frameworks[J]. Applied Chemical Industry, 2019, 48(2): 482-485.
20	Gouterman M. Spectra of porphyrins[J]. Journal of Molecular Spectroscopy, 1961, 6: 138-163.
21	Hamad S, Hernandez N C, Aziz A, et al. Electronic structure of porphyrin-based metal-organic frameworks and their suitability for solar fuel production photocatalysis[J]. Journal of Materials Chemistry A, 2015, 3(46): 23458-23465.
22	Rowsell J L C, Yaghi O M. Effects of functionalization, catenation, and variation of the metal oxide and organic linking units on the low-pressure hydrogen adsorption properties of metal-organic frameworks[J]. Journal of the American Chemical Society, 2006, 128(4): 1304-1315.
23	Wong A G, Matzger A J, Yaghi O M. Exceptional H₂ saturation uptake in microporous metal-organic frameworks[J]. Journal of the American Chemical Society, 2006, 128(11): 3494-3495.
24	Eddaoudi M, Kim J, Rosi N, et al. Systematic design of pore size and functionality in isoreticular MOFs and their application in methane storage[J]. Science, 2002, 295(5554): 469-472.
25	Dybtsev D N, Chun H, Kim K. Three-dimensional metal-organic framework with (3,4)-connected net, synthesized from an ionic liquid medium[J]. Chem. Commun. (Camb.), 2004, 14: 1594-1595.
26	Tian Y Q, Cai C X, Ren X M, et al. The silica-like extended polymorphism of cobalt(Ⅱ) imidazolate three-dimensional frameworks: X-ray single-crystal structures and magnetic properties[J]. Chemistry, 2003, 9(22): 5673-5685.
27	Tian Y Q, Chen Z X, Weng L H, et al. Two polymorphs of cobalt(Ⅱ) imidazolate polymers synthesized solvothermally by using one organic template N,N-dimethylacetamide[J]. Inorganic Chemistry, 2004, 43(15): 4631-4635.
28	Tian Y Q, Zhao Y M, Chen Z X, et al. Design and generation of extended zeolitic metal-organic frameworks (ZMOFs): synthesis and crystal structures of zinc(Ⅱ) imidazolate polymers with zeolitic topologies[J]. Chemistry, 2007, 13(15): 4146-4154.
29	Johnson J A, Zhang X, Reeson T C, et al. Facile control of the charge density and photocatalytic activity of an anionic indium porphyrin framework viain situ metalation[J]. Journal of the American Chemical Society, 2014, 136(45): 15881-15884.
30	Zhao Y, Qi S, Niu Z, et al. Robust corrole-based metal-organic frameworks with rare 9-connected Zr/Hf-oxo clusters[J]. Journal of the American Chemical Society, 2019, 141(36): 14443-14450.
31	Feng D, Gu Z Y, Li J R, et al. Zirconium‐metalloporphyrin PCN‐222: mesoporous metal-organic frameworks with ultrahigh stability As biomimetic catalysts[J]. Angewandte Chemie International Edition, 2012, 51(41): 10307-10310.
32	Feng D, Chung W C, Wei Z, et al. Construction of ultrastable porphyrin Zr metal-organic frameworks through linker elimination[J]. Journal of the American Chemical Society, 2013, 135(45): 17105-17110.
33	Feng D, Gu Z Y, Chen Y P, et al. A highly stable porphyrinic zirconium metal-organic framework with shp-a topology[J]. Journal of the American Chemical Society, 2014, 136(51): 17714-17717.
34	Feng D, Jiang H L, Chen Y P, et al. Metal-organic frameworks based on previously unknown Zr₈/Hf₈ cubic clusters[J]. Inorganic Chemistry, 2013, 52(21): 12661-12667.
35	邹超. 金属卟啉框架材料的设计合成及应用研究[D]. 杭州: 浙江大学, 2013.
	Zou C. Design, syntheses and applications of metalloporphyrinic framework materials[D]. Hangzhou: Zhejiang University, 2013.
36	Wu J X, Hou S Z, Zhang X D, et al. Cathodized copper porphyrin metal-organic framework nanosheets for selective formate and acetate production from CO₂ electroreduction[J]. Chemical Science, 2019, 10(7): 2199-2205.
37	Wang X, Zhang X, Zhou W, et al. An ultrathin porphyrin-based metal-organic framework for efficient photocatalytic hydrogen evolution under visible light[J]. Nano Energy, 2019, 62: 250-258.
38	Fateeva A, Chater P A, Ireland C P, et al. A water-stable porphyrin-based metal-organic framework active for visible-light photocatalysis[J]. Angewandte Chemie International Edition, 2012, 51(30): 7440-7444.
39	Leng F, Liu H, Ding M, et al. Boosting photocatalytic hydrogen production of porphyrinic MOFs: the metal location in metalloporphyrin matters[J]. ACS Catalysis, 2018, 8(5): 4583-4590.
40	王强, 徐睿, 王旭生, 等. 铂纳米颗粒修饰的多孔卟啉基金属-有机框架化合物高效光催化产氢[J]. 无机化学学报, 2017, 33(11): 2038-2044.
	Wang Q, Xu R, Wang X S, et al. Platinum nanoparticle-decorated porous porphyrin-based metal-organic framework for photocatalytic hydrogen production[J]. Chinese Journal of Inorganic Chemistry, 2017, 33(11): 2038-2044.
41	Xiao J D, Shang Q, Xiong Y, et al. Boosting photocatalytic hydrogen production of a metal-organic framework decorated with platinum nanoparticles: the platinum location matters[J]. Angewandte Chemie International Edition, 2016, 55(32): 9389-9393.
42	He T, Chen S, Ni B, et al. Zirconium-porphyrin‐based metal-organic framework hollow nanotubes for immobilization of noble‐metal single atoms[J]. Angewandte Chemie, 2018, 130(13): 3551-3556.
43	Sasan K, Lin Q, Mao C Y, et al. Incorporation of iron hydrogenase active sites into a highly stable metal-organic framework for photocatalytic hydrogen generation[J]. Chemical Communications, 2014, 50(72): 10390-10393.
44	Zuo Q, Liu T, Chen C, et al. Ultrathin metal-organic framework nanosheets with ultrahigh loading of single Pt atoms for efficient visible-light-driven photocatalytic H₂ evolution[J]. Angewandte Chemie, 2019, 131(30): 10304-10309.
45	Xiao J D, Jiang H L. Metal-organic frameworks for photocatalysis and photothermal catalysis[J]. Accounts of Chemical Research, 2018, 52(2): 356-366.
46	Dai F, Fan W, Bi J, et al. A lead-porphyrin metal-organic framework: gas adsorption properties and electrocatalytic activity for water oxidation[J]. Dalton Transactions, 2016, 45(1): 61-65.
47	Li D J, Gu Z G, Zhang W, et al. Epitaxial encapsulation of homodispersed CeO₂ in a cobalt-porphyrin network derived thin film for the highly efficient oxygen evolution reaction[J]. Journal of Materials Chemistry A, 2017, 5(38): 20126-20130.
48	Mirza S, Chen H, Chen S M, et al. Insight into Fe (Salen) encapsulated Co-porphyrin framework derived thin film for efficient oxygen evolution reaction[J]. Crystal Growth & Design, 2018, 18(11): 7150-7157.
49	Paille G, Gomez M, Roch C, et al. A fully noble metal-free photosystem based on cobalt-polyoxometalates immobilized in a porphyrinic metal-organic framework for water oxidation[J]. Journal of the American Chemical Society, 2018, 140(10): 3613-3618.
50	Eddaoudi M, Kim J, Rosi N L, et al. Systematic design of pore size and functionality in isoreticular MOFs and their application in methane storage[J]. Science, 2002, 295(5554): 469-472.
51	Kumar S, Wani M Y, Arranja C T, et al. Porphyrins as nanoreactors in the carbon dioxide capture and conversion: a review[J]. Journal of Materials Chemistry, 2015, 3(39): 19615-19637.
52	Guo R M, Bai J Q, Zhang H, et al. Metal-organic frameworks for catalytic oxidation[J]. Progress in Chemistry, 2016, 28(2/3): 232-243.
53	Xu H Q, Hu J, Wang D, et al. Visible-light photoreduction of CO₂ in a metal-organic framework: boosting electron-hole separation via electron trap states[J]. Journal of the American Chemical Society, 2015, 137(42): 13440-13443.
54	Liu Y, Yang Y, Sun Q, et al. Chemical adsorption enhanced CO₂ capture and photoreduction over a copper porphyrin based metal organic framework[J]. ACS Appl. Mater. Interfaces, 2013, 5(15): 7654-7658.
55	Zhang H, Wei J, Dong J, et al. Efficient visible-light-driven carbon dioxide reduction by a single-atom implanted metal-organic framework[J]. Angewandte Chemie, 2016, 128(46): 14522-14526.
56	Sadeghi N, Sharifnla S, Do T O. Optimization and modeling of CO₂ photoconversion using a response surface methodology with porphyrin-based metal organic framework[J]. Reaction Kinetics, Mechanisms and Catalysis, 2018, 125(1): 411-431.
57	Liu J, Fan Y Z, Li X, et al. Catalytic space engineering of porphyrin metal-organic frameworks for combined CO₂ capture and conversion at a low concentration[J]. ChemSusChem, 2018, 11(14): 2340-2347.
58	He L, Nath J K, Lin Q. Robust multivariate metal-porphyrin frameworks for efficient ambient fixation of CO₂ to cyclic carbonates[J]. Chem. Commun. (Camb.), 2019, 55(3): 412-415.
59	Ye L, Gao Y, Cao S， et al. Assembly of highly efficient photocatalytic CO₂ conversion systems with ultrathin two-dimensional metal-organic framework nanosheets[J]. Applied Catalysis B-Environmental, 2018, 227: 54-60.
60	Zhang X D, Hou S Z, Wu J X, et al. Two‐dimensional metal-organic framework nanosheets with cobalt-porphyrins for high-performance CO₂ electroreduction[J]. Chemistry-A European Journal, 2020, 26(7): 1604-1611.
61	Wang L, Jin P, Huang J, et al. Integration of copper (II)-porphyrin zirconium metal-organic framework and titanium dioxide to construct z-scheme system for highly improved photocatalytic CO₂ reduction[J]. ACS Sustainable Chemistry & Engineering, 2019, 7(18): 15660-15670.
62	Guntern Y T, Pankhurst J R, Vavra J, et al. Nanocrystal/metal-organic framework hybrids as electrocatalytic platforms for CO₂ conversion[J]. Angewandte Chemie International Edition, 2019, 58(36): 12632-12639.
63	Zhou Y, Yang W, Qin M, et al. Self-assembly of metal-organic framework thin films containing metalloporphyrin and their photocatalytic activity under visible light[J]. Applied Organometallic Chemistry, 2016, 30(4): 188-192.
64	He J, Zhang Y, He J, et al. Enhancement of photoredox catalytic properties of porphyrinic metal-organic frameworks based on titanium incorporation via post-synthetic modification[J]. Chem. Commun. (Camb.), 2018, 54(62): 8610-8613.
65	Gao Y X, Xia J, Liu D C, et al. Synthesis of mixed-linker Zr-MOFs for emerging contaminant adsorption and photodegradation under visible light[J]. Chemical Engineering Journal, 2019, 378: 122118.
66	韩雅楠, 张宝, 冯亚青. 铁-锌卟啉框架材料及其可见光催化降解罗丹明[J]. 精细化工, 2019, 36: 1428-1433.
	Han Y N, Zhang B, Feng Y Q. Iron (Ⅲ)-zinc (Ⅱ) porphyrin framework for visible light photocatalytic degradation of rhodamine B[J]. Fine Chemicals, 2019, 36: 1428-1433.
67	Meng A N, Chaihu L X, Chen H H, et al. Ultrahigh adsorption and singlet-oxygen mediated degradation for efficient synergetic removal of bisphenol A by a stable zirconium-porphyrin metal-organic framework[J]. Scientific Reports, 2017, 7(1): 1-9.
68	Zhao Y, Dong Y, Lu F, et al. Coordinative integration of a metal-porphyrinic framework and TiO₂ nanoparticles for the formation of composite photocatalysts with enhanced visible-light-driven photocatalytic activities[J]. Journal of Materials Chemistry A, 2017, 5(29): 15380-15389.
69	Johnson J A, Luo J, Zhang X, et al. Porphyrin-metalation-mediated tuning of photoredox catalytic properties in metal-organic frameworks[J]. ACS Catalysis, 2015, 5(9): 5283-5291.
70	Deenadayalan M S, Sharma N, Verma P K, et al. Visible-light-assisted photocatalytic reduction of nitroaromatics by recyclable Ni(Ⅱ)-porphyrin metal–organic framework (MOF) at RT[J]. Inorganic Chemistry, 2016, 55(11): 5320-5327.
71	Zhao F Y, Li W J, Guo A, et al. Zn (II) porphyrin based nano-/microscale metal-organic frameworks: morphology dependent sensitization and photocatalytic oxathiolane deprotection[J]. RSC Advances, 2016, 6(31): 26199-26202.
72	Chen Y Z, Wang Z U, Wang H, et al. Singlet oxygen-engaged selective photo-oxidation over Pt nanocrystals/porphyrinic MOF: the roles of photothermal effect and Pt electronic state[J]. Journal of the American Chemical Society, 2017, 139(5): 2035-2044.
73	Keum Y, Park S, Chen Y P, et al. Titanium‐carboxylate metal-organic framework based on an unprecedented Ti-oxo chain cluster[J]. Angewandte Chemie, 2018, 130(45): 15068-15072.
74	Xu C, Liu H, Li D, et al. Direct evidence of charge separation in a metal-organic framework: efficient and selective photocatalytic oxidative coupling of amines via charge and energy transfer[J]. Chemical Science, 2018, 9(12): 3152-3158.
75	Shi L, Yang L, Zhang H, et al. Implantation of iron(Ⅲ) in porphyrinic metal organic frameworks for highly improved photocatalytic performance[J]. Applied Catalysis B: Environmental, 2018, 224: 60-68.
76	Ghaleno M R, Ghaffari M M, Khajeh M, et al. Iron species supported on a mesoporous zirconium metal-organic framework for visible light driven synthesis of quinazolin-4(3H)-ones through one-pot three-step tandem reaction[J]. J. Colloid Interface Sci., 2019, 535: 214-226.

[1]	Yin XU, Jie CAI, Lu CHEN, Yu PENG, Fuzhen LIU, Hui ZHANG. Advances in heterogeneous visible light photocatalysis coupled with persulfate activation for water pollution control [J]. CIESC Journal, 2023, 74(3): 995-1009.
[2]	Guojun XI, Zihan LIU, Guangping LEI. Enhanced adsorption and separation of low concentration coalbed methane based on synergistic effect between FeTPPs and CuBTC [J]. CIESC Journal, 2022, 73(9): 3940-3949.
[3]	Mai ZHANG, Yao TIAN, Zhiqi GUO, Ye WANG, Guangjin DOU, Hao SONG. Design and optimization of photocatalysis-biological hybrid system for green synthesis of fuels and chemicals [J]. CIESC Journal, 2022, 73(7): 2774-2789.
[4]	DAI Xiaoye, AN Qingsong, XU Yunting, SHI Lin. Review of waste refrigerant destruction methods [J]. CIESC Journal, 2021, 72(S1): 1-6.
[5]	XIE Qinyin, HUANG Xiaolian, LI Yuan, LI Ling, GE Xuehui, QIU Ting. Design optimization and photocatalytic performance research of TiO₂ planar microreactor [J]. CIESC Journal, 2021, 72(7): 3626-3636.
[6]	ZHANG Jiahe, YUAN Ye, WANG Ming, WANG Zhi, WANG Jixiao. Research progress in polymer-metal-organic frameworks [J]. CIESC Journal, 2021, 72(2): 709-726.
[7]	Bo LIU, Yichang PAN, Rongfei ZHOU, Weihong XING. Research progress on microstructure regulation of molecular sieving membranes for H₂/CH₄ separation [J]. CIESC Journal, 2021, 72(12): 6073-6085.
[8]	Yongqiang DANG,Boni LI,Keke LI,Jianlan ZHANG,Xiangyu FENG,Yating ZHANG. Research progress in photocatalytic reduction of CO₂ with iron-based catalysts [J]. CIESC Journal, 2021, 72(10): 5016-5027.
[9]	REN Jing, TAN Ling, ZHAO Yufei, SONG Yufei. Latest development of ultrathin two-dimensional materials for photocatalytic and electrocatalytic CO₂ reduction [J]. CIESC Journal, 2021, 72(1): 398-424.
[10]	ZHANG Guping, WANG Beibei, ZHOU Zhou, CHEN Dongyun, LU Jianmei. Research progress of semiconductor materials for photocatalytic low concentration nitrogen oxides [J]. CIESC Journal, 2021, 72(1): 259-275.
[11]	Qi ZHOU, Honglei DING, Detong GUO, Weiguo PAN, Wei DU. Recent advances in catalytic methods of CO₂ hydrogenation to clean energy [J]. CIESC Journal, 2020, 71(8): 3428-3443.
[12]	Jingyu HU, Rong YAO, Yuhang PAN, Chao ZHU, Shuang SONG, Yi SHEN. Photo-assisted regeneration of titanium dioxide/layered double hydroxide for removal of organic dyes in water [J]. CIESC Journal, 2020, 71(7): 3296-3303.
[13]	Shuang ZONG, Xinying LIU, Aibing CHEN. Metal-organic frameworks-derived zero-dimensional materials for supercapacitors [J]. CIESC Journal, 2020, 71(6): 2612-2627.
[14]	Yaju CHEN,Zhongxiu LIANG,Xiantai ZHOU,Hongbing JI. CoTPP-TBAB catalyzed tandem transformation of styrene carbonate from styrene in the presence of O₂ and CO₂ [J]. CIESC Journal, 2020, 71(11): 4981-4989.
[15]	Yunlong ZHOU, Xiaoyuan YE, Dongyao LIN. Photocatalytic hydrogen evolution by using corn stover as sacrificial agent under UV light irradiation [J]. CIESC Journal, 2019, 70(7): 2717-2726.