Rhenium Complexes Based on 2-Pyridyl-1,2,3-triazole Ligands: A New Class of CO2 Reduction Catalysts

Inorganic Chemistry

Volumn 56, Issue 5, 2017, Pages 2966-2976

  Ching, H Y Vincent ^{a,b,c,d,e,f,g}   Wang, Xia ^a   He, Menglan ^b,c   Perujo Holland, Noemi ^b,c   Guillot, Régis ^h   Slim, Cyrine ^d,e,f,g   Griveau, Sophie ^d,e,f,g   Bertrand, Hélène C ^b,c   Policar, Clotilde ^b,c   Bedioui, Fethi ^d,e,f,g   Fontecave, Marc ^a  

^a Centre de Recherche Interdisciplinaire en Biologie   (France)

^b ECOLE NORMALE SUPÉRIEURE   (France)

^c SORBONNE UNIVERSITÉ   (France)

^d PSL RESEARCH UNIVERSITY   (France)

^e CNRS   (France)

^f UNIVERSITÉ PARIS DESCARTES   (France)

^g Centre National de la Recherche Scientifique   (France)

^h UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85014526293     PISSN: 00201669     EISSN: 1520510X     Source Type: Journal    
DOI: 10.1021/acs.inorgchem.6b03078     Document Type: Article

References (47)

1. Rakowski Dubois, M.; Dubois, D. L. Development of Molecular Electrocatalysts for CO 2 Reduction and H 2 Production/Oxidation Acc. Chem. Res. 2009, 42 ( 12 ) 1974-1982 10.1021/ar900110c
2. Morris, A. J.; Meyer, G. J.; Fujita, E. Molecular Approaches to the Photocatalytic Reduction of Carbon Dioxide for Solar Fuels Acc. Chem. Res. 2009, 42 ( 12 ) 1983-1994 10.1021/ar9001679
3. Benson, E. E.; Kubiak, C. P.; Sathrum, A. J.; Smieja, J. M. Electrocatalytic and Homogeneous Approaches to Conversion of CO2 to Liquid Fuels Chem. Soc. Rev. 2009, 38 ( 1 ) 89-99 10.1039/B804323J
4. Qiao, J.; Liu, Y.; Hong, F.; Zhang, J. A Review of Catalysts for the Electroreduction of Carbon Dioxide to Produce Low-Carbon Fuels Chem. Soc. Rev. 2014, 43 ( 2 ) 631-675 10.1039/C3CS60323G
5. Rodrigues, N. P.; Obirai, J.; Nyokong, T.; Bedioui, F. Electropolymerized Pyrrole-Substituted Manganese Phthalocyanine Films for the Electroassisted Biomimetic Catalytic Reduction of Molecular Oxygen Electroanalysis 2005, 17 ( 2 ) 186-190 10.1002/elan.200403064
6. Harrison, D. P.; Lapides, A. M.; Binstead, R. A.; Concepcion, J. J.; Méndez, M. A.; Torelli, D. A.; Templeton, J. L.; Meyer, T. J. Coordination Chemistry of Single-Site Catalyst Precursors in Reductively Electropolymerized Vinylbipyridine Films Inorg. Chem. 2013, 52 ( 9 ) 4747-4749 10.1021/ic302472r
7. Blakemore, J. D.; Gupta, A.; Warren, J. J.; Brunschwig, B. S.; Gray, H. B. Noncovalent Immobilization of Electrocatalysts on Carbon Electrodes for Fuel Production J. Am. Chem. Soc. 2013, 135 ( 49 ) 18288-18291 10.1021/ja4099609
8. Chen, X.; Ren, H.; Peng, W.; Zhang, H.; Lu, J.; Zhuang, L. Highly Efficient Molecular Cobalt Electrode for (Photo)electrochemical Hydrogen Evolution J. Phys. Chem. C 2014, 118 ( 36 ) 20791-20798 10.1021/jp5061792
9. Elgrishi, N.; Griveau, S.; Chambers, M. B.; Bedioui, F.; Fontecave, M. Versatile Functionalization of Carbon Electrodes with a Polypyridine Ligand: Metallation and Electrocatalytic H + and CO 2 Reduction Chem. Commun. 2015, 51 ( 14 ) 2995-2998 10.1039/C4CC10027A
10. Rosser, T. E.; Windle, C. D.; Reisner, E. Electrocatalytic and Solar-Driven CO 2 Reduction to CO with a Molecular Manganese Catalyst Immobilized on Mesoporous TiO 2 Angew. Chem., Int. Ed. 2016, 55 ( 26 ) 7388-7392 10.1002/anie.201601038
11. Costentin, C.; Drouet, S.; Robert, M.; Savéant, J.-M. A Local Proton Source Enhances CO2 Electroreduction to CO by a Molecular Fe Catalyst Science 2012, 338 ( 6103 ) 90-94 10.1126/science.1224581
12. Hawecker, J.; Lehn, J.-M.; Ziessel, R. Electrocatalytic Reduction of Carbon Dioxide Mediated by Re(bipy) (CO)3Cl (Bipy = 2,2?-Bipyridine) J. Chem. Soc., Chem. Commun. 1984, 984 ( 6 ) 328 10.1039/C39840000328
13. Smieja, J. M.; Kubiak, C. P. Re(bipy-tBu) (CO)3Cl-Improved Catalytic Activity for Reduction of Carbon Dioxide: IR-Spectroelectrochemical and Mechanistic Studies Inorg. Chem. 2010, 49 ( 20 ) 9283-9289 10.1021/ic1008363
14. Smith, A. P.; Fraser, C. L. Bipyridine Ligands. In Comprehensive Coordination Chemistry II; Elsevier, 2003; Vol. 1, pp 1-23.
15. Bodapati, R.; Sarma, M.; Kanakati, A.; Das, S. K. Asymmetrically Substituted and π-Conjugated 2,2′-Bipyridine Derivatives: Synthesis, Spectroscopy, Computation, and Crystallography J. Org. Chem. 2015, 80 ( 24 ) 12482-12491 10.1021/acs.joc.5b02345
16. Kim, T. Y.; Elliott, A. B. S.; Shaffer, K. J.; John McAdam, C.; Gordon, K. C.; Crowley, J. D. Rhenium(I) Complexes of Readily Functionalized Bidentate Pyridyl-1,2,3-Triazole “click” ligands: A Systematic Synthetic, Spectroscopic and Computational Study Polyhedron 2013, 52, 1391-1398 10.1016/j.poly.2012.05.003
17. Bertrand, H. C.; Clède, S.; Guillot, R.; Lambert, F.; Policar, C. Luminescence Modulations of Rhenium Tricarbonyl Complexes Induced by Structural Variations Inorg. Chem. 2014, 53 ( 12 ) 6204-6223 10.1021/ic5007007
18. Clède, S.; Lambert, F.; Saint-Fort, R.; Plamont, M. A.; Bertrand, H.; Vessières, A.; Policar, C. Influence of the Side-Chain Length on the Cellular Uptake and the Cytotoxicity of Rhenium Triscarbonyl Derivatives: A Bimodal Infrared and Luminescence Quantitative Study Chem.-Eur. J. 2014, 20 ( 28 ) 8714-8722 10.1002/chem.201402471
19. Gjonaj, L.; Roelfes, G. Selective Chemical Modification of DNA with Alkoxy-and Benzyloxyamines Org. Biomol. Chem. 2015, 13 ( 21 ) 6059-6065 10.1039/C5OB00595G
20. Juríček, M.; Kouwer, P. H. J.; Rehák, J.; Sly, J.; Rowan, A. E. A Novel Modular Approach to Triazole-Functionalized Phthalocyanines Using Click Chemistry J. Org. Chem. 2009, 74 ( 1 ) 21-25 10.1021/jo802078f
21. Zhu, X. Q.; Zhang, M. T.; Yu, A.; Wang, C. H.; Cheng, J. P. Hydride, Hydrogen Atom, Proton, and Electron Transfer Driving Forces of Various Five-Membered Heterocyclic Organic Hydrides and Their Reaction Intermediates in Acetonitrile J. Am. Chem. Soc. 2008, 130 ( 8 ) 2501-2516 10.1021/ja075523m
22. Bolje, A.; Urankar, D.; Košmrlj, J. Synthesis and NMR Analysis of 1,4-Disubstituted 1,2,3-Triazoles Tethered to Pyridine, Pyrimidine, and Pyrazine Rings Eur. J. Org. Chem. 2014, 2014 ( 36 ) 8167-8181 10.1002/ejoc.201403100
23. Carlsson, A.-C. C.; Mehmeti, K.; Uhrbom, M.; Karim, A.; Bedin, M.; Puttreddy, R.; Kleinmaier, R.; Neverov, A. A.; Nekoueishahraki, B.; Gräfenstein, J.; Rissanen, K.; Erdélyi, M. Substituent Effects on the [N-I-N] + Halogen Bond J. Am. Chem. Soc. 2016, 138 ( 31 ) 9853-9863 10.1021/jacs.6b03842
24. Sheldrick, G. M. SHELXS-97, Program for Crystal Structure Solution; University of Göttingen: Göttingen, Germany, 1997.
25. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures from Diffraction Data; University of Göttingen: Göttingen, Germany, 1997.
26. Farrugia, L. J. Suite for Small-Molecule Single-Crystal Crystallography J. Appl. Crystallogr. 1999, 32 ( 4 ) 837-838 10.1107/S0021889899006020
27. Tsuboyama, A.; Okada, S.; Takiguchi, T.; Suzuki, K.; Miura, S.; Moriyama, T.; Igawa, S.; Kamatani, J.; Furugori, M.; Iwawaki, H. Electroluminescent Device Using Metal Coordination Compound. US 2004/0013905 A1, Jan. 22, 2004.
28. Combs, A. P.; Sparks, R. B.; Maduskuie, T. P., Jr.; Rodgers, J. D. Tricyclic Heterocycles as BET Protein Inhibitors. WO2014/143768 A1, Sept 18, 2014.
29. Kurz, P.; Probst, B.; Spingler, B.; Alberto, R. Ligand Variations in [ReX(diimine) (CO)3] Complexes: Effects on Photocatalytic CO2 Reduction Eur. J. Inorg. Chem. 2006, 2006 ( 15 ) 2966-2974 10.1002/ejic.200600166
30. Wolff, M.; Munoz, L.; François, A.; Carrayon, C.; Seridi, A.; Saffon, N.; Picard, C.; Machura, B.; Benoist, E. Tricarbonylrhenium Complexes from 2-Pyridyl-1,2,3-Triazole Ligands Bearing a 4-Substituted Phenyl Arm: A Combined Experimental and Theoretical Study Dalton Trans. 2013, 42 ( 19 ) 7019-7031 10.1039/c3dt33071k
31. Lo, W. K. C.; Huff, G. S.; Cubanski, J. R.; Kennedy, A. D. W.; McAdam, C. J.; McMorran, D. A.; Gordon, K. C.; Crowley, J. D. Comparison of Inverse and Regular 2-Pyridyl-1,2,3-triazole “click” Complexes: Structures, Stability, Electrochemical, and Photophysical Properties Inorg. Chem. 2015, 54 ( 4 ) 1572-1587 10.1021/ic502557w
32. Bard, A. J.; Faulkner, L. R. Electrochemical Methods, 2nd ed.; John Wiley & Sons, Ltd, 2001.
33. Baur, J. E.; Wightman, R. M. Diffusion Coefficients Determined with Microelectrodes J. Electroanal. Chem. Interfacial Electrochem. 1991, 305 ( 1 ) 73-81 10.1016/0022-0728(91)85203-2
34. Smieja, J. M.; Sampson, M. D.; Grice, K. A.; Benson, E. E.; Froehlich, J. D.; Kubiak, C. P. Manganese as a Substitute for Rhenium in CO2 Reduction Catalysts: The Importance of Acids Inorg. Chem. 2013, 52 ( 5 ) 2484-2491 10.1021/ic302391u
35. Johnson, F. P. A.; George, M. W.; Hartl, F.; Turner, J. J. Electrocatalytic Reduction of CO 2 Using the Complexes [Re(bpy) (CO) 3 L] N (N = + 1, L = P(OEt) 3, CH 3 CN; N = 0, L = Cl-, Otf-; Bpy = 2,2′-Bipyridine; Otf-= CF 3 SO 3) as Catalyst Precursors: Infrared Spectroelectrochemical Investigation Organometallics 1996, 15 ( 15 ) 3374-3387 10.1021/om960044+
36. Saravanan, K.; Keith, J. A. Standard Redox Potentials, pK a S, and Hydricities of Inorganic Complexes under Electrochemical Conditions and Implications for CO 2 Reduction Dalt. Trans 2016, 45 ( 39 ) 15336-15341 10.1039/C6DT02371A
37. Felton, G. A. N.; Vannucci, A. K.; Okumura, N.; Lockett, L. T.; Evans, D. H.; Glass, R. S.; Lichtenberger, D. L. Hydrogen Generation from Weak Acids: Electrochemical and Computational Studies in the [(η 5-C 5 H 5)Fe(CO) 2 ] 2 System Organometallics 2008, 27 ( 18 ) 4671-4679 10.1021/om800366h
38. Foit, S.; Eichel, R.-A.; Vinke, I. C.; de Haart, L. G. J. Power-to-Syngas-an Enabling Technology for the Transition of the Energy System? Production of Tailored Synfuels and Chemicals Using Renewably Generated Electricity Angew. Chem., Int. Ed. 2016, 1 10.1002/anie.201607552
39. Liyanage, N. P.; Dulaney, H. A.; Huckaba, A. J.; Jurss, J. W.; Delcamp, J. H. Electrocatalytic Reduction of CO 2 to CO With Re-Pyridyl-NHCs: Proton Source Influence on Rates and Product Selectivities Inorg. Chem. 2016, 55 ( 12 ) 6085-6094 10.1021/acs.inorgchem.6b00626
40. Hawecker, J.; Lehn, J.-M.; Ziessel, R. Efficient Photochemical Reduction of CO 2 to CO by Visible Light Irradiation of Systems Containing Re(bipy) (CO) 3 X or Ru(bipy) 3 2+ - Co 2+ Combinations as Homogeneous Catalysts J. Chem. Soc., Chem. Commun. 1983, 9 ) 536-538 10.1039/C39830000536
41. Hori, H.; Ishitani, O.; Koike, K.; Johnson, F. P. A.; Ibusuki, T. Efficient Carbon Dioxide Photoreduction by Novel Metal Complexes and Its Reaction Mechanisms Energy Convers. Manage. 1995, 36 ( 6-9 ) 621-624 10.1016/0196-8904(95)00082-O
42. Hawecker, J.; Lehn, J.-M.; Ziessel, R. Photochemical Reduction of Carbon Dioxide to Formate Mediated by Ruthenium Bipyridine Complexes as Homogeneous Catalysts J. Chem. Soc., Chem. Commun. 1985, 20 ( 2 ) 56 10.1039/c39850000056
43. Juris, A.; Balzani, V.; Belser, P.; von Zelewsky, A. Characterization of the Excited State Properties of Some New Photosensitizers of the Ruthenium (Polypyridine) Family Helv. Chim. Acta 1981, 64 ( 7 ) 2175-2182 10.1002/hlca.19810640723
44. 2 Reduction Using Rhenium(I) Complexes Based on Mechanistic Studies J. Am. Chem. Soc. 2008, 130 ( 6 ) 2023-2031 10.1021/ja077752e
45. Gibson, D. H.; Yin, X. Synthesis and Reactions of Fac-Re(dmbpy) (CO) 3 X (Dmbpy = 4,4′-Dimethyl-2,2′-Bipyridyl; X = COOH, COOMe, H, OH, and OCHO) J. Am. Chem. Soc. 1998, 120 ( 43 ) 11200-11201 10.1021/ja982284h
46. Hayashi, Y.; Kita, S.; Brunschwig, B. S.; Fujita, E. Involvement of a Binuclear Species with the Re-C(O)O-Re Moiety in CO 2 Reduction Catalyzed by Tricarbonyl Rhenium(I) Complexes with Diimine Ligands: Strikingly Slow Formation of the Re-Re and Re-C(O)O-Re Species from Re(dmb) (CO) 3 S (Dmb = 4,4′-Dimethyl-2 J. Am. Chem. Soc. 2003, 125 ( 39 ) 11976-11987 10.1021/ja035960a
47. Morimoto, T.; Nakajima, T.; Sawa, S.; Nakanishi, R.; Imori, D.; Ishitani, O. CO 2 Capture by a Rhenium(I) Complex with the Aid of Triethanolamine J. Am. Chem. Soc. 2013, 135 ( 45 ) 16825-16828 10.1021/ja409271s