Citation: Liang ZHAO, Shao-Shuai CHU, Jun-Kai CAI, Jian-Wei WEI, Ya-Nan LI, Chun-Ying DUAN. Metal-Organic Triangles with NADH Mimics for Photocatalytic Hydrogen Production[J]. Chinese Journal of Inorganic Chemistry, ;2021, 37(5): 769-777. doi: 10.11862/CJIC.2021.092 shu

Metal-Organic Triangles with NADH Mimics for Photocatalytic Hydrogen Production

State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, Liaoning 116024, China

Corresponding author: Liang ZHAO, zhaol@dlut.edu.cn
Received Date: 28 October 2020
Revised Date: 28 December 2020

Figures(7)

By incorporating two different reduced nicotinamide adenine dinucleotide (NADH) mimics within the ligand backbone, two positively charged cobalt-based metal-organic triangular hosts Co-L¹ and Co-L² (H₂L¹=5'-(benzo[d]thiazol-2-yl)-N'⁴, N'''''^4″-bis((E)-pyridin-2-ylmethylene)-[1, 1': 3', 1″-terphenyl]-4, 4″-dicarbohydrazide, H₂L²=5'(benzo[d]imidazol-2-yl)-N'⁴, N'''''^4″-bis((E)-pyridin-2-ylmethylene)-[1, 1': 3', 1″-terphenyl]-4, 4″-dicar bohydrazide) have been prepared in high yield and characterized as a redox vehicle for the construction of an artificial photosynthesis (AP) system. By taking advantage of electrostatic interaction to facilitate the formation of host-guest complexes, anionic ruthenium-based photosensitizer[Ru(dcbpy)₃]^4- (dcbpy=2, 2'-bipyridine-4, 4'-dicarboxylic acid) was encapsulated into the suitable cavity of hosts to improve photoinduced electron transfer (PET) processes and to promote photocatalytic hydrogen production. Compared with metal-organic triangular Co-L³ without NADH mimics (H₂L³=5'-methyl-N'⁴, N'''''^4″-bis((E)-pyridin-2-ylmethylene)-[1, 1': 3', 1″-terphenyl]-4, 4″-dicarbohydrazide) and mononuclear catalyst Co-L⁴ (HL⁴=(E)-N'-(pyridin-2-ylmethylene)benzohydrazide) containing the same coordination environment and without NADH mimics, photocatalytic hydrogen production efficiency of the host-guest supramolecular photosynthetic systems could increase 1.6 and 6 times, respectively. The higher catalytic activity is attributed to the formation of host-guest complex between catalyst Co-L¹ and Co-L² and photosensitizer[Ru(dcbpy)₃]^4- and the introduction of NADH mimics benefiting the PET process between the catalyst and photosensitizer.
- metal-organic macrocycle,
- NADH mimic,
- host-guest complex,
- photoinduced electron transfer,
- photocatalytic hydrogen production
1. [1]
  Zhou C, Shi R, Waterhouse G I N, Zhang T R. Coord. Chem. Rev. , 2020, 419: 213399 doi: 10.1016/j.ccr.2020.213399
2. [2]
  Ran J R, Zhang J, Yu J G, Jaroniec M, Qiao S Z. Chem. Soc. Rev. , 2014, 43: 7787-7812 doi: 10.1039/C3CS60425J
3. [3]
  Li X, Yu J G, Jaroniec M. Chem. Soc. Rev. , 2016, 45: 2603-2636 doi: 10.1039/C5CS00838G
4. [4]
  Wu K, Hou Y J, Lu Y L, Fan Y Z, Fan Y N, Yu H J, Li K, Pan M, Su C Y. Chem. Eur. J. , 2019, 25: 11903-11909 doi: 10.1002/chem.201901612
5. [5]
  Xiao T X, Zhong W W, Zhou L, Xu L X, Sun X Q, Elmes R B P, Hu X Y, Wang L Y. Chin. Chem. Lett. , 2019, 30: 31-36 doi: 10.1016/j.cclet.2018.05.034
6. [6]
  Li X, Yu J G, Low J X, Fang Y P, Xiao J, Chen X B. J. Mater. Chem. A, 2015, 3: 2485-2534 doi: 10.1039/C4TA04461D
7. [7]
  Xie A, Pan Z H, Yu M, Luo G G, Sun D. Chin. Chem. Lett. , 2019, 30: 225-228 doi: 10.1016/j.cclet.2018.05.003
8. [8]
  WU Q Y, ZHANG C X, SUN K, JIANG H L. Acta Chim. Sinica, 2020, 78: 688-694 doi: 10.11862/CJIC.2020.075
9. [9]
  Pan Y T, Qian Y Y, Zheng X S, Chu S Q, Yang Y J, Ding C M, Wang X, Yu S H, Jiang H L. Natl. Sci. Rev. , 2021, 8(1): nwaa224 doi: 10.1093/nsr/nwaa224
10. [10]
  Frischmann P D, Mahata K, Würthner F. Chem. Soc. Rev. , 2013, 42: 1847-1870 doi: 10.1039/C2CS35223K
11. [11]
  Pan M, Wu K, Zhang J H, Su C Y. Coord. Chem. Rev. , 2020, 378: 333-349
12. [12]
  Lehn J M. Supramolecular Chemistry: Concepts and Perspectives. Weinheim: Wiley-VCH, 1995: 2-6
13. [13]
  Jing X, He C, Yang Y, Duan C Y. J. Am. Chem. Soc. , 2015, 137: 3967-3974 doi: 10.1021/jacs.5b00832
14. [14]
  Brown C J, Toste F D, Bergman R G, Raymond K N. Chem. Rev. , 2015, 115: 3012-3035 doi: 10.1021/cr4001226
15. [15]
  He C, Wang J, Zhao L, Liu T, Zhang J, Duan C Y. Chem. Commun. , 2013, 49: 627-629
16. [16]
  Yang L, He C, Liu X, Zhang J, Sun H, Guo H M. Chem. Eur. J. , 2016, 22: 5253-5260 doi: 10.1002/chem.201504975
17. [17]
  Nurttila S S, Becker R, Hessels J, Woutersen S, Reek J N H. Chem. Eur. J. , 2018, 24: 16395-16406 doi: 10.1002/chem.201803351
18. [18]
  Cai J K, Zhao L, Wei J W, He C, Long S R, Duan C Y. Chem. Commun. , 2019, 55: 8524-8527 doi: 10.1039/C9CC03871J
19. [19]
  YANG L L, JING X, HE C, DUAN C Y. Chinese J. Inorg. Chem. , 2017, 33(6): 913-922
20. [20]
  LI H C, LI M F, HE C, DUAN C Y. Chinese J. Inorg. Chem. , 2018, 34(1): 11-19
21. [21]
  ZHANG W Y, YANG Y, HUANG H L, JING X, DUAN C Y. Chinese J. Inorg. Chem. , 2020, 36(10): 1988-1996 doi: 10.11862/CJIC.2020.206
22. [22]
  Yadav R K, Oh G H, Park N J, Kumar A, Kong K J, Baeg J O. J. Am. Chem. Soc. , 2014, 136: 16728-16731 doi: 10.1021/ja509650r
23. [23]
  Sun Z T, Lonsdale R, Ilie A, Li G Y, Zhou J H, Reetz M T. ACS Catal. , 2016, 6: 1598-1605 doi: 10.1021/acscatal.5b02752
24. [24]
  Litman Z C, Wang Y J, Zhao H M, Hartwig J F. Nature, 2018, 560: 355-359 doi: 10.1038/s41586-018-0413-7
25. [25]
  McSkimming A, Colbran S B. Chem. Soc. Rev. , 2013, 42: 5439-5488 doi: 10.1039/c3cs35466k
26. [26]
  Feng Y S, Yang C Y, Huang Q, Xu H J. Tetrahedron, 2012, 68: 5053-5059 doi: 10.1016/j.tet.2012.04.047
27. [27]
  Zhu C, Saito K, Yamanaka M, Akiyama T. Acc. Chem. Res. , 2015, 48: 388-398 doi: 10.1021/ar500414x
28. [28]
  Gao S, Huang S, Duan Q, Hou J H, Jiang D Y, Liang Q C, Zhao J X. Int. J. Hydrogen Energy, 2014, 39: 10434-10444 doi: 10.1016/j.ijhydene.2014.05.003
29. [29]
  Zhao L, Wei J W, Lu J H, He C, Duan C Y. Angew. Chem. Int. Ed. , 2017, 56: 8692-8696 doi: 10.1002/anie.201702926
30. [30]
  Zhao L, Wang J, Wu P Y, He C, Guo X Y, Duan C Y. Sci. Rep. , 2017, 7: 14347 doi: 10.1038/s41598-017-14728-8
31. [31]
  Wei J W, Zhao L, He C, Zheng S J, Reek J N H, Duan C Y. J. Am. Chem. Soc. , 2019, 141: 12707-12716 doi: 10.1021/jacs.9b05351
32. [32]
  Zhao L, Cai J K, Li Y N, Wei J W, Duan C Y. Nat. Commun. , 2020, 11: 2903 doi: 10.1038/s41467-020-16714-7
33. [33]
  Zhao L, Wei J W, Zhang J, He C, Duan C Y. Angew. Chem. Int. Ed. , 2017, 56: 15284-15288 doi: 10.1002/anie.201707676
34. [34]
  Zhao L, Wei J W, Zhang F L, He C, Zheng S J, Duan C Y. RSC Adv. , 2017, 7: 48989-48993 doi: 10.1039/C7RA09285G
35. [35]
  Zhou J, Zhang Y Z, Yu G C, Crawley M R, Fulong C R P, Friedman A E, Sengupta S, Sun J F, Li Q, Huang F H, Cook T R. J. Am. Chem. Soc. , 2018, 140: 7730-7736 doi: 10.1021/jacs.8b04929
36. [36]
  Baffert C, Artero V, Fontecave M. Inorg. Chem. , 2007, 46: 1817-1824 doi: 10.1021/ic061625m
37. [37]
  Artero V, Chavarot-Kerlidou M, Fontecave M. Angew. Chem. Int. Ed. , 2011, 50: 7238-7266 doi: 10.1002/anie.201007987
38. [38]
  Jiang P J, Guo Z J. Coord. Chem. Rev. , 2004, 248: 205-229 doi: 10.1016/j.cct.2003.10.013
39. [39]
  Nelissen H F M, Kercher M, De Cola L, Feiters M C, Nolte R J M. Chem. Eur. J. , 2002, 8: 5407-5414 doi: 10.1002/1521-3765(20021202)8:23<5407::AID-CHEM5407>3.0.CO;2-P
40. [40]
  Zheng S J, Zhao L, Wei J W, He C, Liu G Z, Duan C Y. Inorg. Chem. Commun. , 2019, 109: 107558 doi: 10.1016/j.inoche.2019.107558
41. [41]
  Mei J, Leung N L C, Kwok R T K, Lam J W Y, Tang B Z. Chem. Rev. , 2015, 115: 11718-11940 doi: 10.1021/acs.chemrev.5b00263
42. [42]
  Wu K, Li K, Chen S, Hou Y J, Lu Y L, Wang J S, Wei M J, Pan M, Su C Y. Angew. Chem. Int. Ed. , 2020, 59: 2639-2643
43. [43]
  Odella E, Wadsworth B L, Mora S J, Goings J J, Huynh M T, Gust D, Moore T A, Moore G F, Hammes-Schiffer S, Moore A L. J. Am. Chem. Soc. , 2019, 141: 14057-14061 doi: 10.1021/jacs.9b06978
44. [44]
  Ranjeesh K C, Illathvalappil R, Veer S D, Peter J, Wakchaure V C, Goudappagouda, Raj K V, Kurungot S, Babu S S. J. Am. Chem. Soc. , 2019, 141: 14950-14954 doi: 10.1021/jacs.9b06080
45. [45]
  Dong J F, Wang M, Zhang P, Yang S Q, Liu J Y, Li X Q, Sun L C. J. Phys. Chem. C, 2011, 115: 15089-15096 doi: 10.1021/jp2040778
46. [46]
  Zhang S Q, Han L, Li L N, Cheng J, Yuan D Q, Luo J H. Cryst. Growth Des. , 2013, 13: 5466-5472 doi: 10.1021/cg401438j
47. [47]
  Elliott C M, Caramori S, Bignozzi C A. Langmuir, 2005, 21: 3022-3027
1. [1]
  Juan WANG , Zhongqiu WANG , Qin SHANG , Guohong WANG , Jinmao LI . NiS and Pt as dual co-catalysts for the enhanced photocatalytic H₂ production activity of BaTiO₃ nanofibers. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1719-1730. doi: 10.11862/CJIC.20240102
2. [2]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
3. [3]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
4. [4]
  Yuanpei ZHANG , Jiahong WANG , Jinming HUANG , Zhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077
5. [5]
  Zhengyu Zhou , Huiqin Yao , Youlin Wu , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-. doi: 10.3866/PKU.WHXB202312010
6. [6]
  Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO₂ cycloaddition over W₁₈O₄₉/NH₂-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349
7. [7]
  Qiangqiang SUN , Pengcheng ZHAO , Ruoyu WU , Baoyue CAO . Multistage microporous bifunctional catalyst constructed by P-doped nickel-based sulfide ultra-thin nanosheets for energy-efficient hydrogen production from water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1151-1161. doi: 10.11862/CJIC.20230454
8. [8]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
9. [9]
  Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351
10. [10]
  Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO₂-0.39IrO_x composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
11. [11]
  Lu XU , Chengyu ZHANG , Wenjuan JI , Haiying YANG , Yunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431
12. [12]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
13. [13]
  Qiuyang LUO , Xiaoning TANG , Shu XIA , Junnan LIU , Xingfu YANG , Jie LEI . Application of a densely hydrophobic copper metal layer in-situ prepared with organic solvents for protecting zinc anodes. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1243-1253. doi: 10.11862/CJIC.20240110
14. [14]
  Jing SU , Bingrong LI , Yiyan BAI , Wenjuan JI , Haiying YANG , Zhefeng Fan . Highly sensitive electrochemical dopamine sensor based on a highly stable In-based metal-organic framework with amino-enriched pores. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1337-1346. doi: 10.11862/CJIC.20230414
15. [15]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
16. [16]
  Bo YANG , Gongxuan LÜ , Jiantai MA . Nickel phosphide modified phosphorus doped gallium oxide for visible light photocatalytic water splitting to hydrogen. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 736-750. doi: 10.11862/CJIC.20230346
17. [17]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
18. [18]
  Endong YANG , Haoze TIAN , Ke ZHANG , Yongbing LOU . Efficient oxygen evolution reaction of CuCo₂O₄/NiFe-layered bimetallic hydroxide core-shell nanoflower sphere arrays. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 930-940. doi: 10.11862/CJIC.20230369
19. [19]
  Yan LIU , Jiaxin GUO , Song YANG , Shixian XU , Yanyan YANG , Zhongliang YU , Xiaogang HAO . Exclusionary recovery of phosphate anions with low concentration from wastewater using a CoNi-layered double hydroxide/graphene electronically controlled separation film. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1775-1783. doi: 10.11862/CJIC.20240043
20. [20]
  Donghui PAN , Yuping XU , Xinyu WANG , Lizhen WANG , Junjie YAN , Dongjian SHI , Min YANG , Mingqing CHEN . Preparation and in vivo tracing of ⁶⁸Ga-labeled PM_2.5 mimetic particles for positron emission tomography imaging. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 669-676. doi: 10.11862/CJIC.20230468

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(898)
HTML views(162)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142