Citation: WANG Qing, MA Cheng-Bing, CHEN Hui, HUANG De-Guang, CHEN Chang-Neng. Five-heterocyclic-biphosphinesubstituted Fe-only Hydrogenase Mimic: Synthesis, Characterization and Properties[J]. Chinese Journal of Structural Chemistry, ;2016, 35(12): 1972-1979. doi: 10.14102/j.cnki.0254-5861.2011-1211 shu

Five-heterocyclic-biphosphinesubstituted Fe-only Hydrogenase Mimic: Synthesis, Characterization and Properties

a.
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China
b.
University of Chinese Academy of Sciences, Beijing 100039, China

Corresponding author: CHEN Chang-Neng, ccn@fjirsm.ac.cn
Received Date: 22 March 2016
Accepted Date: 2 June 2016

Fund Project: the NNSFC 21231003 and 21203195

Figures(4)

A new five-heterocyclic-biphosphine-substituted Fe-only hydrogenase mimic,[(μ-pdt)Fe₂(CO)₅]₂(PTP) (1), has been synthesized at room temperature. 1·H₂O crystallizes in triclinic system, space group P1, with a=11.5897(4), b=13.6156(4), c=18.0333(6)Å, α=76.306(3), β=72.742(3), γ=68.939(3)°, V=2508.84(14)Å³, D_c=1.570 g/cm³, Z=2, M_r=1186.37, F(000)=1204, the final R=0.0748, and wR=0.2012. In the tetranuclear complex 1·H₂O, each[2Fe2S] butterfly unit is attached to one P atom of the diphosphine bridge and exhibits a square-pyramidal geometry. Complex 1 was characterized by elemental analysis, IR spectra, UV-vis absorption spectra, ¹H-NMR and ³¹P-NMR. The cyclic voltammetry behavior of compound 1 was investigated as well.
- Fe-only hydrogenase mimic,
- spectral analysis,
- cyclic voltammetry
1. [1]
  Lawrence J. D, Li H, Rauchfuss T. B, Benard M, Rohmer M. M. Diiron azadithiolates as models for the iron-only hydrogenase active site: synthesis, structure, and stereoelectronics[J]. Angew. Chem., Int. Ed., 2001,40:1768-1771. doi: 10.1002/(ISSN)1521-3773
2. [2]
  Ott S, Kritikos M, Akermark B, Sun L C, Lomoth R. A biomimetic pathway for hydrogen evolution from a model of the iron hydrogenase active site[J]. Angew. Chem., Int. Ed., 2004,43:1006-1009. doi: 10.1002/(ISSN)1521-3773
3. [3]
  Felton G. A. N, Mebi C. A, Petro B. J, Vannucci A. K, Evans D. H, Glass R. S, Lichtenberger D. L. Review of electrochemical studies of complexes containing the Fe2S2 core characteristic of[J]. J. Organomet. Chem., 2009,694:2681-2699. doi: 10.1016/j.jorganchem.2009.03.017
4. [4]
  Baltazar C. S. A, Marques M. C, Soares C. M, DeLacey A. M, Pereira I. A. C, Matias P. M. Nickel-iron-selenium hydrogenases-an overview[J]. Eur. J. Inorg. Chem., 2011,7:948-962.
5. [5]
  Frey, M. Hydrogenases: hydrogen-activating enzymes. ChemBioChem. 2002, 2-3, 153-160.
6. [6]
  Peters J. W, Lanzilotta W. N, Lemon B. J, Seefeldt L. C. X-ray crystal structure of the Fe-only hydrogenase (CpI) from Clostridium pasteurianum to 1.8 angstrom resolution[J]. Science, 1998,282:1853-1858. doi: 10.1126/science.282.5395.1853
7. [7]
  Peters J. W. Structure and mechanism of iron-only hydrogenases[J]. Curr. Opin. Struc. Biol., 1999,9:670-676. doi: 10.1016/S0959-440X(99)00028-7
8. [8]
  Huo F. W, Hou J, Chen G. C, Guo D. M, Peng X. J. [FeFe]-Hydrogen models: overpotential control for electrocatalytic H2 production by tuning of the ligand π-acceptor ability. Eur. J[J]. Inorg. Chem., 2010,25:3942-3951.
9. [9]
  Chong D, Georgakaki I. P, Mejia-Rodriguez R, Sanabria-Chinchilla J, Soriaga M. P, Darensbourg M. Y. Electrocatalysis of hydrogen production by active site analogues of the iron hydrogenase enzyme: structure/function relationships[J]. Dalton Trans., 2003,21:4158-4163.
10. [10]
  Schwartz L, Eilers G, Eriksson L, Gogoll A, Lomoth R, Ott S. Iron hydrogenase active site mimic holding a proton and a hydride[J]. Chem. Commun., 2006,5:520-522.
11. [11]
  Si G, Wang W. G, Wang H. Y, Tung C. H, Wu L. Z. Facile synthesis and functionality-dependent electrochemistry of Fe-only hydrogenase mimics[J]. Inorg. Chem., 2008,47:8101-8111. doi: 10.1021/ic800676y
12. [12]
  Gloaguen F, Lawrence J. D, Rauchfuss T. B, Benard M, Rohmer M. M. Bimetallic carbonyl thiolates as functional models for Fe-only hydrogenases[J]. Inorg. Chem., 2002,41:6573-6582. doi: 10.1021/ic025838x
13. [13]
  Gloaguen F, Lawrence J. D, Rauchfuss T. B. Biomimetic hydrogen evolution catalyzed by an iron carbonyl thiolate[J]. J. Am. Chem. Soc., 2001,123:9476-9477. doi: 10.1021/ja016516f
14. [14]
  Chong D. S, Georgakaki I. P, Mejia-Rodriguez R, Samabria-Chinchilla J, Soriaga M. P, Darensbourg M. Y. Electrocatalysis of hydrogen production by active site analogues of the iron hydrogenase enzyme: structure /function relationships[J]. Dalton Trans., 2003,21:4158-4163.
15. [15]
  Capon J. F, Gloaguen F, Schollhammer P, Talarmin J. Electrochemical proton reduction by thiolate-bridged hexacarbonyldiiron clusters[J]. J. Electroanal. Chem., 2004,566:241-247. doi: 10.1016/j.jelechem.2003.11.032
16. [16]
  Song L. C, Yang Z, Bian H. Z, Hu Q. M. Novel single and double diiron oxadithiolates as models for the active site of[J]. Organometallics, 2004,13:3082-3084.
17. [17]
  Si Y, Charreteur K, Capon J. F, Gloaguen F. Pétillon, F. Y, Schollhammer, P. Talarmin, J. Non-innocent bma ligand in a dissymetrically disubstituted diiron dithiolate related to the active site of the[J]. J. Inorg. Biochem., 2010,104:1038-1042. doi: 10.1016/j.jinorgbio.2010.05.011
18. [18]
  Cui H. H, Wu N. N, Wang J. Y, Hu M. Q, Wen H. M, Chen C. N. Pyridyl- and pyrimidyl-phosphine-substituted[J]. J. Organomet. Chem., 2014,767:46-53. doi: 10.1016/j.jorganchem.2014.04.026
19. [19]
  Capon J. F, Gloaguen F, Schollhammer P, Talarmin J. Activation of proton by the two-electron reduction of a di-iron organometallic complex[J]. J. Electroanal. Chem., 2006,595:47-52. doi: 10.1016/j.jelechem.2006.06.005
20. [20]
  Felton G. A. N, Vannucci A. K, Chen J. Z, Lockett L. T, Okumura N, Petro B. J, Zakai U. I, Evans D. H, Glass R. S, Lichtenberger D. L. Hydrogen generation from weak acids: electrochemical and computational studies of a diiron hydrogenase mimic[J]. J. Am. Chem. Soc., 2007,41:12521-12530.
21. [21]
  Chen L, Wang M, Gloaguen F, Zheng D. H, Zhang P. L, Sun L. C. Multielectron-transfer templates via consecutive two-electron transformations: iron-sulfur complexes relevant to biological enzymes[J]. Chem. Eur. J., 2012,18:13968-13973. doi: 10.1002/chem.v18.44
22. [22]
  Chen L, Wang M, Gloaguen F, Zheng D. H, Zhang P. L, Sun L. C. Tetranuclear iron complexes bearing benzenetetrathiolate bridges as four-electron transformation templates and their electrocatalytic properties for proton reduction[J]. Inorg. Chem., 2013,52:1798-1806. doi: 10.1021/ic301647u
23. [23]
  Kang D. M, Kim S. G, Lee S. J, Park J. K, Park K. M, Shin S. C. Synthesis, characterization, and absorption spectra of metallamacrocycles,[J]. Soc., 2005,9:1390-1394.
24. [24]
  Sevillano P, Fuhr O, Hampe O, Lebedkin S, Neiss C, Ahlrichs R, Fenske D, Kappes M. M. Synthesis, characterization and quantum mechanical calculations of[J]. J. Inorg. Chem., 2007,33:5163-5167.
25. [25]
  Stott T. L, Wolf M. O, Patrick B. O. Structural and electronic properties of phosphino(oligothiophene) gold(I) complexes[J]. Inorg. Chem., 2005,3:620-627.
26. [26]
  Brown, J. M.; Lucy, A. R. Trans-bis(diphenylphosphino)cyclopropane; a ligand selective for binuclear complexation with ca. 4.5 ? intermetallic separation. J. Organomet. Chem. 1986, 1-2, 241-246.
27. [27]
  Hourihane R, Gray G, Spalding T, Deeney T. Synthesis and spectroscopic characterisation of compounds with formula[J]. Chem., 2002,642:40-47.
28. [28]
  Li P, Wang M, He C. J, Li G. H, Liu X. Y, Chen C. N, Akermark B, Sun L. C. Influence of tertiary phosphanes on the coordination configurations and electrochemical properties of iron hydrogenase model complexes: crystal structures of[J]. J. Inorg. Chem., 2005,12:2506-2513.
29. [29]
  Messelhauser J, Lorenz I. P, Haug K, Hiller W. Synthesis and structure of the ethenedithiolato complex[J]. Z. Naturforsch Teil. B, 1985,40:1064-1067.
30. [30]
  Stott T. L, Wolf M. O. Spectroscopic study of phosphine-substituted oligothiophenes[J]. J. Phys. Chem. B, 2004,108:18815-18819. doi: 10.1021/jp047037g
31. [31]
  Sheldrick, G. M. SHELXS97, Program for the Solution of Crystal Structure. University of G?ttingen, Germany 1997.
32. [32]
  Sheldrick, G. M. SHELXL97, Program for the Refinement of Crystal Structure. University of G?ttingen, Germany 1997.
33. [33]
  Zhao X; Georgakaki I. P, Miller M. L, Mejia-Rodriguez R, Chiang C. Y, Darensbourg M. Y. Catalysis of H2/D2 scrambling and other H/D exchange processes by[J]. Inorg. Chem., 2002,15:3917-3928.
34. [34]
  Ott S, Borgstrom M, Kritikos M, Lomoth R, Bergquist J, Akermark B, Hammarstrom L, Sun L. C. Model of the iron hydrogenase active site covalently linked to a ruthenium photosensitizer: synthesis and photophysical properties[J]. Inorg. Chem., 2004,15:4683-4692.
35. [35]
  Gloaguen F, Lawrence J. D, Rauchfuss T. B, Benard M, Rohmer M. M. Bimetallic carbonyl thiolates as functional models for Fe-Only hydrogenases[J]. Inorg. Chem., 2002,25:6573-6582.
36. [36]
  Gao W. M, Liu J. H, Akermark B, Sun L. C. Bidentate phosphine ligand based Fe2S2-containing macromolecules: synthesis, characterization, and catalytic electrochemical hydrogen production[J]. Inorg. Chem., 2006,23:9169-9171.
37. [37]
  Matthews S. L, Heinekey D. M. A carbonyl-rich bridging hydride complex relevant to the Fe-Fe hydrogenase active site[J]. Inorg. Chem., 2010,49:9746-9748. doi: 10.1021/ic1017328
38. [38]
  Gao W. M, Ekstrom J, Liu J. H, Chen C. N, Eriksson L, Weng L. H, Akermark B, Sun L. H. Binuclear iron-sulfur complexes with bidentate phosphine ligands as active site models of Fe-hydrogenase and their catalytic proton reduction[J]. Inorg. Chem., 2007,46:1981-1991. doi: 10.1021/ic0610278
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