Citation: Jing ZHANG, Yang YANG, Zhong WEI, Xu JING, Chun-Ying DUAN. Ferrocene-Functionalized Metal-Organic Macrocycles Mimicking Hydrogenase for Photocatalytic Nitro Reduction[J]. Chinese Journal of Inorganic Chemistry, ;2022, 38(12): 2469-2478. doi: 10.11862/CJIC.2022.237 shu

Ferrocene-Functionalized Metal-Organic Macrocycles Mimicking Hydrogenase for Photocatalytic Nitro Reduction

Zhang Dayu College of Chemistry, Dalian University of Technology, Dalian, Liaoning 116024, China

Corresponding author: Xu JING, xjing@dlut.edu.cn
Received Date: 19 April 2022
Revised Date: 5 September 2022

Figures(4)

Two novel metal-organic macrocycles (M_Fe and M_Cu) were constructed using the flexible and redox-active ferrocene ligand. The macrocycles effectively quenched the fluorescence of organic dyes and exhibited the capability to trigger the photoinduced electron transfer. Due to relatively lower reduction potentials, M_Cu exhibited better catalytic features for proton reduction and could better catalyze the reduction of nitro compounds. The large size of the substrates leads to a decreased efficiency in the nitro reduction process. The Michaelis-Menten mechanism was used to verify the photocatalytic system, which revealed the importance of the interaction between substrate and catalyst.
- metal-organic macrocycle,
- ferrocene,
- photocatalytic,
- supramolecule,
- Michaelis-Menten mechanism
1. [1]
  Eisenmesser E Z, Bosco D A, Akke M, Kern D. Enzyme Dynamics During Catalysis[J]. Science, 2002,295:1520-1523. doi: 10.1126/science.1066176
2. [2]
  Ueda Y, Ito H, Fujita D, Fujita M. Permeable Self-Assembled Molecular Containers for Catalyst Isolation Enabling Two-Step Cascade Reactions[J]. J. Am. Chem. Soc., 2017,139(17):6090-6093. doi: 10.1021/jacs.7b02745
3. [3]
  Cullen W, Metherell A J, Wragg A B, Taylor C G P, Williams N H, Ward M D. Catalysis in a Cationic Coordination Cage Using a Cavity-Bound Guest and Surface-Bound Anions: Inhibition, Activation, and Autocatalysis[J]. J. Am. Chem. Soc., 2018,140(8):2821-2828. doi: 10.1021/jacs.7b11334
4. [4]
  Jing X, Yang Y, He C, Chang Z D, Reek J N H, Duan C Y. Control of Redox Events by Dye Encapsulation Applied to Light-Driven Splitting of Hydrogen Sulfide[J]. Angew. Chem. Int. Ed., 2017,56(39):11759-11763. doi: 10.1002/anie.201704327
5. [5]
  Hooley R J. Taking on the Turnover Challenge[J]. Nat. Chem., 2016,8(3):202-204. doi: 10.1038/nchem.2461
6. [6]
  Li J W, Ren Y W, Qi C R, Jiang H F. The First Porphyrin-Salen Based Chiral Metal-Organic Framework for Asymmetric Cyanosilylation of Aldehydes[J]. Chem. Commun., 2017,53(58):8223-8226. doi: 10.1039/C7CC03499G
7. [7]
  Wu F, Qiu L G, Ke F, Jiang X. Copper Nanoparticles Embedded in Metal-Organic Framework MIL-101(Cr) as a High Performance Catalyst for Reduction of Aromatic Nitro Compounds[J]. Inorg. Chem. Commun., 2013,32:5-8. doi: 10.1016/j.inoche.2013.03.003
8. [8]
  Ma Y Y, Peng H Y, Liu J N, Wang Y H, Hao X L, Feng X J, Khan S U, Tan H Q, Li Y G. Polyoxometalate-Based Metal-Organic Frameworks for Selective Oxidation of Aryl Alkenes to Aldehydes[J]. Inorg. Chem., 2018,57(7):4109-4116. doi: 10.1021/acs.inorgchem.8b00282
9. [9]
  Yang Y, Li H N, Jing X, Wu Y C, Shi Y P, Duan C Y. Dye-Loaded Metal-Organic Helical Capsules Applied to the Combination of Photocatalytic H₂S Splitting and Nitroaromatic Hydrogenation[J]. Chem. Commun., 2022,58(6):807-810. doi: 10.1039/D1CC06166F
10. [10]
  Jin Y H, Zhang Q Q, Zhang Y Q, Duan C Y. Electron Transfer in the Confined Environments of Metal-Organic Coordination Supramolecular Systems[J]. Chem. Soc. Rev., 2020,49(15):5561-5600. doi: 10.1039/C9CS00917E
11. [11]
  Jing X, He C, Zhao L, Duan C Y. Photochemical Properties of Host-Guest Supramolecular Systems with Structurally Confined Metal-Organic Capsules[J]. Acc. Chem. Res., 2019,52(1):100-109. doi: 10.1021/acs.accounts.8b00463
12. [12]
  LI H C, LI M F, HE C, DUAN C Y. Construction of a Noble-Metal-Free Nickel Metal-Organic Macrocycle for Photocatalytic Hydrogen Production[J]. Chinese J. Inorg. Chem., 2018,34(1):11-19.
13. [13]
  YANG L L, JING X, HE C, DUAN C Y. Photocatalytic Hydrogen Production Based on Cobalt-Thiosemicarbazone Complex with the Xanthene Dye Moiety[J]. Chinese J. Inorg. Chem., 2017,33(6):913-922.
14. [14]
  ZHANG W Y, YANG Y, HUANG H L, JING X, DUAN C Y. Photocatalytic Hydrogen Production Based on Metal-Organic Triangle Modified by Fluorescein Isothiocyanate[J]. Chinese J. Inorg. Chem., 2020,36(10):1988-1996.
15. [15]
  Liu H L, Chang L N, Chen L Y, Li Y W. Nanocomposites of Platinum/Metal-Organic Frameworks Coated with Metal-Organic Frameworks with Remarkably Enhanced Chemoselectivity for Cinnamaldehyde Hydrogenation[J]. ChemCatChem, 2016,8(5):946-951. doi: 10.1002/cctc.201501256
16. [16]
  Zhang J Z, An B, Li Z, Cao Y H, Dai Y H, Wang W Y, Zeng L Z, Lin W B, Wang C. Neighboring Zn-Zr Sites in a Metal-Organic Framework for CO₂ Hydrogenation[J]. J. Am. Chem. Soc., 2021,143(23):8829-8837. doi: 10.1021/jacs.1c03283
17. [17]
  Vasdev R A S, Findlay J A, Garden A L, Crowley J D. Redox Active [Pd₂L₄]⁴⁺ Cages Constructed from Rotationally Flexible 1, 1'-Disubstituted Ferrocene Ligands[J]. Chem. Commun., 2019,55(52):7506-7509. doi: 10.1039/C9CC03321A
18. [18]
  Horikoshi R. Discrete Metal Complexes from N-Heterocyclic Ferrocenes: Structural Diversity by Ligand Design[J]. Coord. Chem. Rev., 2013,257(3/4):621-637.
19. [19]
  Plajer A J, Rizzuto F J, Krbek L K S, Gisbert Y, Agramunt V M, Nitschke J R. Oxidation Triggers Guest Dissociation During Reorganization of an Fe^Ⅱ ₄L₆ Twisted Parallelogram[J]. Chem. Sci., 2020,11(38):10399-10404. doi: 10.1039/D0SC04352D
20. [20]
  Coleman M H. Graphical Analysis of Enzyme Kinetic Data[J]. Nature, 1965,205:798-799. doi: 10.1038/205798a0
21. [21]
  Michaelis L, Menten M L. The Kinetics of Invertin Action[J]. FEBS Lett., 2013,587(17):2712-2720. doi: 10.1016/j.febslet.2013.07.015
22. [22]
  Armarego W L F, Chai C L L. Purification of Laboratory Chemicals. 6th ed. Burlington: Elsevier, 2009: 27-28
23. [23]
  Li M X, Cai P, Duan C Y, Lu F, Xie J, Meng Q J. Octanuclear Metallocyclic Ni₄Fc₄ Compound: Synthesis, Crystal Structure, and Electrochemical Sensing for Mg²⁺[J]. Inorg. Chem., 2004,43:5174-5176. doi: 10.1021/ic049530c
24. [24]
  SMART, Data Collection Software, Version 5.629. Bruker AXS Inc., Madison, WI, 2003.
25. [25]
  SAINT, Data Reduction Software, Version 6.54. Bruker AXS Inc., Madison, WI, 2003.
26. [26]
  Bourhis L J, Dolomanov O V, Gildea R J, Howard J A K, Puschmann H. The Anatomy of a Comprehensive Constrained, Restrained Refinement Program for the Modern Computing Environment-Olex2 Dissected[J]. Acta Crystallogr. Sect. A, 2015,A71:59-75.
27. [27]
  Dolomanov O V, Bourhis L J, Gildea R J, Howard J A K, Puschmann H. OLEX2: A Complete Structure Solution, Refinement and Analysis Program[J]. J. Appl. Cryst., 2009,42:339-341. doi: 10.1107/S0021889808042726
28. [28]
  Sheldrick G M. A Short History of SHELX[J]. Acta Crystallogr. Sect. A, 2008,A64:112-122.
29. [29]
  Du P W, Eisenberg R. Catalysts Made of Earth-Abundant Elements (Co, Ni, Fe) for Water Splitting: Recent Progress and Future Challenges[J]. Energy Environ. Sci., 2012,5(3):6012-6021.
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