Iron-iron hydrogenase active subunit covalently linking to organic chromophore for light-driven hydrogen evolution

International Journal of Hydrogen Energy

Volumn 39, Issue 20, 2014, Pages 10434-10444

  Gao, Shang ^a   Huang, Shuai ^a   Duan, Qian ^a   Hou, Jianhua ^a   Jiang, Dayong ^a   Liang, Qingcheng ^a   Zhao, Jianxun ^a  

^a CHANGCHUN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Hydrogen evolution; Iron iron hydrogenase; Organic chromophore; Photo induced electron transfer; Photocatalysis

Indexed keywords

CHROMOPHORES; ELECTRON TRANSITIONS; HYDROGEN; PHOTOCATALYSIS; PHOTOCATALYSTS; PHOTOSENSITIZERS; X RAY CRYSTALLOGRAPHY;

HYDROGEN EVOLUTION; HYDROGENASES; LASER FLASH PHOTOLYSIS; ORGANIC CHROMOPHORES; PHOTO-INDUCED ELECTRON TRANSFER; PHOTOCATALYTIC EFFICIENCY; SACRIFICIAL ELECTRON DONORS; STEADY-STATE SPECTROSCOPIES;

IRON;

EID: 84902539808     PISSN: 03603199     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijhydene.2014.05.003     Document Type: Article

References (69)

1. M. Balat Potential importance of hydrogen as a future solution to environmental and transportation problems Int J Hydrogen Energy 33 2008 4013 4029
2. N.Z. Muradov, and T.N. Veziroǧlu "Green" path from fossil-based to hydrogen economy: an overview of carbon-neutral technologies Int J Hydrogen Energy 33 2008 6804 6839
3. H.B. Gray Powering the planet with solar fuel Nat Chem 1 2009 7
4. J. Barber Photosynthetic energy conversion: natural and artificial Chem Soc Rev 38 2009 185 196
5. D.J. Evans, and C.J. Pickett Chemistry and the hydrogenases Chem Soc Rev 32 2003 268 275
6. S. Kim, D.P. Lu, S. Park, and G.Y. Wang Production of hydrogenases as biocatalysts Int J Hydrogen Energy 37 2012 15833 15840
7. W. Lubitz, H. Ogata, O. Rüdiger, and E. Reijerse Hydrogenases Chem Rev 114 2014 4081 4148
8. Y. Nicolet, C. Piras, P. Legrand, E.C. Hatchikian, and J.C. Fontecilla-Camps Desulfovibrio desulfuricans iron hydrogenase: the structure shows unusual coordination to an active site Fe binuclear center Structure 7 1999 13 23
9. M.W.W. Adams, and E.I. Stiefel Biological hydrogen production: not so elementary Science 282 1998 1842 1843
10. R. Cammack Bioinorganic chemistry: hydrogenase sophistication Nature 397 1999 214 215
11. M.Y. Darensbourg, E.J. Lyon, X. Zhao, and I.P. Georgakaki The organometallic active site of [Fe]hydrogenase: models and entatic states Proc Natl Acad Sci USA 100 2003 3683 3688
12. I.P. Georgakaki, L.M. Thomson, E.J. Lyon, M.B. Hall, and M.Y. Darensbourg Fundamental properties of small molecule models of Fe-only hydrogenase: computations relative to the definition of an entatic state in the active site Coord Chem Rev 238-239 2003 255 266
13. C. Tard, X.M. Liu, S.K. Ibrahim, M. Bruschi, L. De Gioia, and S.C. Davies et al. Synthesis of the H-cluster framework of iron-only hydrogenase Nature 433 2005 610 613
14. C. Tard, and C.J. Pickett Structural and functional analogues of the active sites of the [Fe]-, [NiFe]-, and [FeFe]-hydrogenases Chem Rev 109 2009 2245 2274
15. F. Gloaguen, and T.B. Rauchfuss Small molecule mimics of hydrogenases: hydrides and redox Chem Soc Rev 38 2009 100 108
16. J.F. Capon, F. Gloaguen, F.Y. Petillon, P. Schollhammer, and J. Talarmin Electron and proton transfers at diiron dithiolate sites relevant to the catalysis of proton reduction by the [FeFe]-hydrogenases Coord Chem Rev 253 2009 1476 1494
17. 2 core characteristic of [FeFe]-hydrogenases including catalysis by these complexes of the reduction of acids to form dihydrogen J Organomet Chem 694 2009 2681 2699
18. 2 formation by [FeFe] hydrogenase models Energy Environ Sci 4 2011 2340 2352
19. S. Ott, M. Kritikos, B. Åkermark, L.C. Sun, and R. Lomoth Synthesis and structure of a biomimetic model of the iron hydrogenase active site covalently linked to a ruthenium photosensitizer Angew Chem Int Ed 42 2003 3285 3288
20. S. Ott, M. Borgström, M. Kritikos, R. Lomoth, J. Bergquist, and B. Åkermark et al. Model of the iron hydrogenase active site covalently linked to a ruthenium photosensitizer: synthesis and photophysical properties Inorg Chem 43 2004 4683 4692
21. L.C. Sun, B. Åkermark, and S. Ott Iron hydrogenase active site mimics in supramolecular systems aiming for light-driven hydrogen production Coord Chem Rev 249 2005 1653 1663
22. J. Ekström, M. Abrahamsson, C. Olson, J. Bergquist, F.B. Kaynak, and L. Eriksson et al. Bio-inspired, side-on attachment of a ruthenium photosensitizer to an iron hydrogenase active site model Dalt Trans 38 2006 4599 4606
23. L.C. Song, M.Y. Tang, F.H. Su, and Q.M. Hu A biomimetic model for the active site of iron-only hydrogenases covalently bonded to a porphyrin photosensitizer Angew Chem Int Ed 45 2006 1130 1133
24. A.M. Kluwera, R. Kaprea, F. Hartl, M. Lutz, A.L. Spek, and A.M. Brouwer et al. Self-assembled biomimetic [2Fe2S]-hydrogenasebased photocatalyst for molecular hydrogen evolution Proc Natl Acad Sci USA 106 2009 10460 10465
25. A.P.S. Samuel, D.T. Co, C.L. Stern, and M.R. Wasielewski Ultrafast photodriven intramolecular electron transfer from a zinc porphyrin to a readily reduced diiron hydrogenase model complex J Am Chem Soc 132 2010 8813 8815
26. P. Poddutoori, T.C. Dick, A.P.S. Samuel, C.H. Kim, M.T. Vagnini, and M.R. Wasielewski Photoinitiated multistep charge separation in ferrocene-zinc porphyrin-diiron hydrogenase model complex triads Energy Environ Sci 4 2011 2441 2450
27. 3(bpy) (py) photosensitizer aiming for light-driven hydrogen production C R Chim 11 2008 915 921
28. W.G. Wang, F. Wang, H.Y. Wang, G. Si, C.H. Tung, and L.Z. Wu Photocatalytic hydrogen evolution by [FeFe] hydrogenase mimics in homogeneous solution Chem Asian J 8 2010 1796 1803
29. H.Y. Wang, G. Si, W.N. Cao, W.G. Wang, Z.J. Li, and F. Wang et al. A triad [FeFe] hydrogenase system for light-driven hydrogen evolution Chem Commun 47 2011 8406 8408
30. J.H. Liu, and W.N. Jiang Photoinduced hydrogen evolution in supramolecular devices with a rhenium photosensitizer linked to FeFe-hydrogenase model complexes Dalt Trans 41 2012 9700 9707
31. F. Wang, W.G. Wang, H.Y. Wang, G. Si, C.H. Tung, and L.Z. Wu Artificial photosynthetic systems based on [FeFe]-hydrogenase mimics: the road to high efficiency for light-driven hydrogen evolution ACS Catal 2 2012 407 416
32. W.G. Wang, F. Wang, H.Y. Wang, C.H. Tung, and L.Z. Wu Electron transfer and hydrogen generation from a molecular dyad: platinum(II) alkynyl complex anchored to [FeFe] hydrogenase subsite mimic Dalt Trans 41 2012 2420 2426
33. H.H. Cui, M.Q. Hu, H.M. Wen, G.L. Chai, C.B. Ma, and H. Chen et al. Efficient [FeFe] hydrogenase mimic dyads covalently linking to iridium photosensitizer for photocatalytic hydrogen evolution Dalt Trans 41 2012 13899 13907
34. + to [2Fe2S] model complexes of the iron-only hydrogenase active site Inorg Chem 46 2007 3813 3815
35. Y. Na, M. Wang, J.X. Pan, P. Zhang, B. Åkermark, and L.C. Sun Visible light-driven electron transfer and hydrogen generation catalyzed by bioinspired [2Fe2S] complexes Inorg Chem 47 2008 2805 2810
36. 2] catalyst with high turnover numbers Dalt Trans 39 2010 1204 1206
37. D. Streich, Y. Astuti, M. Orlandi, L. Schwartz, R. Lomoth, and L. Hammarstrom et al. High-turnover photochemical hydrogen production catalyzed by a model complex of the [FeFe]-hydrogenase active site Chem Eur J 16 2010 60 63
38. H.Y. Wang, W.G. Wang, G. Si, F. Wang, C.H. Tung, and L.Z. Wu Photocatalytic hydrogen evolution from rhenium(I) complexes to [FeFe] hydrogenase mimics in aqueous SDS micellar systems: a biomimetic pathway Langmuir 26 2010 9766 9771
39. W.N. Cao, F. Wang, H.Y. Wang, B. Chen, K. Feng, and C.H. Tung et al. Photocatalytic hydrogen production from a simple water-soluble [FeFe]-hydrogenase model system Chem Commun 48 2012 8081 8083
40. S. Pullen, H.H. Fei, A. Orthaber, S.M. Cohen, and S. Ott Enhanced photochemical hydrogen production by a molecular diiron catalyst incorporated into a metal-organic framework J Am Chem Soc 135 2013 16997 17003
41. S. Yu, F. Wang, J.J. Wang, H.Y. Wang, B. Chen, and K. Feng et al. Light-driven hydrogen evolution system with glutamic-acid-modified zinc porphyrin as photosensitizer and [FeFe]-hydrogenase model as catalyst Pure Appl Chem 85 7 2013 1405 1413
42. L.C. Song, M.Y. Tang, S.Z. Mei, J.H. Huang, and Q.M. Hu The active site model for iron-only hydrogenases coordinatively bonded to a metalloporphyrin photosensitizer Organometallics 26 2007 1575 1577
43. X.Q. Li, M. Wang, S.Q. Zhang, J.X. Pan, Y. Na, and J.H. Liu et al. Noncovalent assembly of a metalloporphyrin and an iron hydrogenase active-site model: photo-induced electron transfer and hydrogen generation J Phys Chem B 112 2008 8198 8202
44. 2 production in aqueous solution with host-guest inclusions formed by insertion of an FeFe-hydrogenase mimic and an organic dye into cyclodextrins Energy Environ Sci 5 2012 8220 8224
45. 2 production Chem Commun 49 2013 627 629
46. F. Wang, W.G. Wang, X.J. Wang, H.Y. Wang, C.H. Tung, and L.Z. Wu A highly efficient photocatalytic system for hydrogen production by a robust hydrogenase mimic in an aqueous solution Angew Chem Int Ed 50 2011 3193 3197
47. 2] hydrogenase mimic as hydrogen evolution catalyst ChemSusChem 5 2012 849 853
48. 2 production in water Angew Chem Int Ed 52 2013 8134 8138
49. 2ase mimics on CdSe QDs for photosynthetic hydrogen evolution in water Energy Environ Sci 6 2013 2597 2602
50. J.X. Jian, Q. Liu, Z.J. Li, F. Wang, X.B. Li, and C.B. Li et al. Chitosan confinement enhances hydrogen photogeneration from a mimic of the diiron subsite of [FeFe]-hydrogenase Nat Commun 4 2013 2695
51. S.J. Ji, and H.B. Shi Synthesis and fluorescent property of some novel benzothiazoyl pyrazoline derivatives containing aromatic heterocycle Dyes Pigments 70 2006 246 250
52. Y. Nicolet, A.L. de Lacey, X. Vernède, V.M. Fernandez, E.C. Hatchikian, and J.C. Fontecilla-Camps Crystallographic and FTIR spectroscopic evidence of changes in fe coordination upon reduction of the active site of the Fe-only hydrogenase from Desulfovibrio desulfuricans J Am Chem Soc 123 2001 1596 1601
53. H.J. Fan, and M.B. Hall A capable bridging ligand for Fe-only hydrogenase: density functional calculations of a low-energy route for heterolytic cleavage and formation of dihydrogen J Am Chem Soc 123 2001 3828 3829
54. G. Berggren, A. Adamska, C. Lambertz, T.R. Simmons, J. Esselborn, and M. Atta et al. Biomimetic assembly and activation of [FeFe]-hydrogenases Nature 499 2013 66 69
55. J. Esselborn, C. Lambertz, A. Adamska, T. Simmons, G. Berggren, and J. Noth et al. Spontaneous activation of [FeFe]-hydrogenases by an inorganic [2Fe] active site mimic Nat Chem Biol 9 2013 607 609
56. D.W. Hein, R.J. Alheim, and J.J. Leavitt The use of polyphosphoric acid in the synthesis of 2-aryl- and 2-alkyl-substituted benzimidazoles, benzoxazoles and benzothiazoles J Am Chem Soc 79 1957 427 429
57. 9 and comparisons with analogous sulfide clusters J Organomet Chem 250 1983 429 438
58. x (x = 5, 6) Chem Commun 16 2001 1482 1483
59. Software packages SMART and SAINT 1996 Siemens Energy & Automation Inc Madison, Wisconsin
60. G.M. Sheldrick SADABS absorption correction program 1996 University of Göffingen Germany
61. G.M. Sheldrick SHELXTL 97 program for the refinement of crystal structure 1997 University of Göffingen Germany
62. M.M. Henary, and C.J. Fahrni Excited state intramolecular proton transfer and metal ion complexation of 2-(2'-hydroxyphenyl)benzazoles in aqueous solution J Phys Chem A 106 2002 5210 5220
63. G. Eilers, L. Schwartz, M. Stein, G. Zampella, L. de Gioia, and S. Ott et al. Ligand versus metal protonation of an iron hydrogenase active site mimic Chem Eur J 13 2007 7075 7084
64. D. Baskaran, J.W. Mays, X.P. Zhang, and M.S. Bratcher Carbon nanotubes with covalently linked porphyrin antennae: photoinduced electron transfer J Am Chem Soc 127 2005 6916 6917
65. D. Rehm, and A. Weller Kinetics of fluorescence quenching by electron and H-atom transfer Isr J Chem 8 1970 259 271
66. T. Iijima, A. Momotake, Y. Shinohara, T. Sato, Y. Nishimura, and T. Arai Excited-state intramolecular proton Transfer of Naphthalene-fused 2-(2'-Hydroxyaryl)benzazole family J Phys Chem A 114 2010 1603 1609
67. P. Yang, J.Z. Zhao, W.H. Wu, X.R. Yu, and Y.F. Liu Accessing the long-lived triplet excited states in bodipy-conjugated 2-(2-Hydroxyphenyl) benzothiazole/benzoxazoles and applications as organic triplet photosensitizers for photooxidations J Org Chem 77 2012 6166 6178
68. B.G. Zhang, Y.J. Li, R. Liu, T.M. Pritchett, J.E. Haley, and W.F. Sun Extending the bandwidth of reverse saturable absorption in platinum complexes using two-photon-initiated excited-state absorption ACS Appl Mater Interf 5 2013 565 572
69. S.J. Borg, T. Bergamini, S.P. Best, M. Razavet, X. Liu, and C.J. Pickett Electron transfer at a dithiolate-bridged diiron assembly: electrocatalytic hydrogen evolution J Am Chem Soc 126 2004 16988 16999