A High Molar Extinction Coefficient Bisterpyridyl Homoleptic Ru(II) Complex with trans-2-Methyl-2-butenoic Acid Functionality: Potential Dye for Dye-Sensitized Solar Cells
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis
2.2. Infrared Spectra Studies of the Ligand and Complex
2.3. 1H and 13C-NMR Spectroscopic Studies
2.4. Electronic Absorption Spectroscopic Study of the [Ru(L1)2(PF6)2] Complex
2.5. Emission Spectroscopic Study of the [Ru(L1)2(PF6)2] Complex
2.6. Electrochemical Study
3. Experimental Section
3.1. Synthesis of 4′-(trans-2-Methyl-2-butenoic Acid)-2,2′:6′,2″-Terpyridine (L1)
3.2. Synthesis of Bis-4′-(trans-2-Methyl-2-butenoic Acid)-2,2′:6′,2″-Terpyridyl Ruthenium(II) Bis-Hexafluorophosphate Complex [Ru(L1)2(PF6)2]
4. Conclusions
Supplementary Information
ijms-13-03511-s001.pdfAcknowledgements
- Conflict of InterestThe authors hereby declare no conflict of interest.
References
- O’Regan, B.; Gratzel, M. A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films. Nature 1991, 353, 737–740. [Google Scholar]
- Hagfeldt, A.; Gratzel, M. Light-induced redox reactions in nanocrystalline systems. Chem. Rev 1995, 95, 49–68. [Google Scholar]
- Peter, L.M. Dye-sensitized nanocrystalline solar cells. Phys. Chem. Chem. Phys 2007, 9, 2630–2642. [Google Scholar]
- Park, H.; Bae, E.; Lee, J.-J.; Park, J.; Choi, W. Effect of the anchoring group in Ru-bipyridyl sensitizers on the photoelectrochemical behaviour of dye-sensitized TiO2 electrodes: Carboxylate versus Phosphonate linkages. J. Phys. Chem. B 2006, 110, 8740–8749. [Google Scholar]
- Zaban, A.; Ferrrere, S.; Sprague, J.; Gregg, B.A. pH-dependent redox potential induced in a sensitizing dye by adsorption onto TiO2. J. Phys. Chem. B 1997, 101, 55–57. [Google Scholar]
- Kelly, C.A.; Farzad, F.; Thompson, D.W.; Stipkala, J.M.; Meyer, G.J. Cation-controlled interfacial charge injection in sensitized nanocrystalline TiO2. Langmuir 1999, 15, 7047–7054. [Google Scholar]
- Pichot, F.; Gregg, B.A. The photovoltage-determining mechanism in dye-sensitized solar cells. J. Phys. Chem. B 2000, 104, 6–10. [Google Scholar]
- Fallapour, R.A. Photochemical and thermal reactions of azido-oligopyridines: Diazepinones, a new class of metal-complex ligands. Helv. Chim. Acta 2000, 83, 384–393. [Google Scholar]
- Renouard, T.; Fallapour, R.A.; Nazeeruddin, M.K.; Humphry-Baker, R.; Gorelsky, S.I.; Lever, B.P.; Gratzel, M. Novel ruthenium sensitizers containing functionalized hybrid tetradentate ligands: synthesis, characterization, and INDO/S analysis. Inorg. Chem 2002, 41, 367–378. [Google Scholar]
- Argazzi, R.; Bignozzi, C.A.; Heimer, T.A.; Meyer, G.J. Remote electron injection from supramolecular sensitizers. Inorg. Chem 1997, 36, 2–3. [Google Scholar]
- Wolpher, H.; Sinha, S.; Pan, J.; Johansson, A.; Lundqvist, M.J.; Persson, P.; Lomoth, R.; Bergquist, J.; Sun, L.; Sundstrolm, V.; et al. Synthesis and electron transfer studies of ruthenium-terpyridine-based dyads attached to nanostructured TiO2. Inorg. Chem 2007, 46, 638–651. [Google Scholar]
- Asbury, J.B.; Ellingson, R.J.; Ghosh, H.N.; Ferrere, S.; Nozik, A.J.; Lian, T. Femtosecond IR study of excited-state relaxation and electron-injection dynamics of [Ru(dcbpy)2(NCS)2] in solution and on nanocrystalline TiO2 and Al2O3 thin films. J. Phys. Chem. B 1999, 103, 3110–3119. [Google Scholar]
- Winter, C.; Sizman, R.; Vant Hull, L. Solar Power Plants; Springer-Verlag: New York, NY, USA, 1991; Volume Chapter 2. [Google Scholar]
- Nazeeruddin, M.K.; Pechy, P.; Renouard, T.; Zakeeruddin, S.M.; Humphry-Baker, R.; Comte, P.; Liska, P.; Cevey, L.; Costa, E.; Shklover, V.; et al. Engineering of efficient panchromatic sensitizers for nanocrystalline TiO2-based solar cells. J. Am. Chem. Soc 2001, 123, 1613–1624. [Google Scholar]
- Balzani, V.; Scandola, F. Supramolecular Photochemistry; Ellis Horwood: Chichester, UK, 1991. [Google Scholar]
- Meyer, T.J. Photochemistry of metal coordination complexes: Metal to ligand charge transfer excited states. Pure Appl. Chem 1986, 58, 1193–1206. [Google Scholar]
- Meyer, T.J; Huynh, M.H.V. The remarkable reactivity of high oxidation state ruthenium and osmium polypyridyl complexes. Inorg. Chem 2003, 42, 8140–8160. [Google Scholar]
- Bonnet, S.; Collin, J.P.; Sauvage, J.P. Synthesis and photochemistry of a two-position Ru(terpy)(phen)(L)2+ scorpionate complex. Inorg. Chem 2006, 45, 4024–4034. [Google Scholar]
- Karidi, K.; Garoufis, A.; Tsipis, A.; Hadjiliadis, N.; Dulk, H.; Reedijk, J.J. Synthesis, characterization, in-vitro antitumor activity, DNA-binding properties and electronic structure (DFT) of the new complex cis-(Cl, Cl)[RuIICl2(NO+)(terpy)]Cl. Chem. Soc. Dalton Trans 2005, 1176–1187. [Google Scholar]
- Juris, A.; Balzani, V.; Barigelletti, F.; Campagna, S.; Belser, P.; Zelewsky, A.V. Ruthenium(II) polypyridine complexes: Photophysics, photochemistry, electrochemistry, and chemilunescence. Coord. Chem. Rev 1988, 84, 85–277. [Google Scholar]
- Treadway, J.A.; Loeb, B.; Lopez, R.; Anderson, P.A.; Keene, F.R.; Meyer, T.J. Effect of delocalization and rigidity in the acceptor ligand on MLCT excited-state decay. Inorg. Chem 1996, 35, 2242–2246. [Google Scholar]
- Nazeeruddin, M.K.; Kay, A.; Rodicio, I.; Humphry-Baker, R.; Muller, E.; Liska, P.; Vlachopoulos, N.; Gratzel, M. Conversion of light to electricity by cis-X2(dcbpy)2Ru(II) CT sensitizers on nanocrystalline TiO2 electrodes. J. Am. Chem. Soc 1993, 115, 6382–6390. [Google Scholar]
- Treadway, J.A.; Strouse, G.F.; Ruminski, R.R.; Meyer, T.J. Long-lived near-infrared MLCT emitters. Inorg. Chem 2001, 40, 4508–4509. [Google Scholar]
- Treadway, J.A.; Moss, J.A.; Meyer, T.J. Visible region photooxidation on TiO2 with a chromophore-catalyst molecular assembly. Inorg. Chem 1999, 38, 4386–4387. [Google Scholar]
- Zakeeruddin, S.M.; Nazeeruddin, M.K.; Humphry-Baker, R.; Gratzel, M.; Shklover, V. Stepwise assembly of tris-heteroleptic polypyridyl complexes of ruthenium(II). Inorg. Chem 1998, 37, 5251–5259. [Google Scholar]
- Adeloye, A.O.; Ajibade, P.A. A high molar extinction coefficient mono-anthracenyl bipyridyl heteroleptic ruthenium(II) complex: Synthesis, photophysical and electrochemical properties. Molecules 2011, 16, 4615–4631. [Google Scholar]
- Adeloye, A.O.; Ajibade, P.A. Synthesis, characterization and preliminary investigation of the electroredox properties of anthracenyl-functionalized terpyridyl ligands. Tetrahedron Lett 2011, 52, 274–277. [Google Scholar]
- Adeloye, A.O. Synthesis, photophysical and electrochemical properties of a mixed-bipyridyl-phenanthrolyl ligand Ru(II) heteroleptic complex having trans-2-Methyl-2-butenoic acid functionalities. Molecules 2011, 16, 8353–8367. [Google Scholar]
- Duffy, N.W.; Dobson, K.D.; Gordon, K.C.; Robinson, B.H.; McQuillan, A.J. In situ infrared spectroscopic analysis of the adsorption of ruthenium(II) bipyridyl dicarboxylic acid photosensitizers to TiO2 in aqueous solutions. Chem. Phys. Lett 1997, 266, 451–455. [Google Scholar]
- Coates, J. Interpretation of infrared spectra, a practical approach. In Encyclopedia of Analytical Chemistry; Meyers, R.A., Ed.; John Wiley & Sons Ltd: Chichester, UK, 2000; pp. 10815–10837. [Google Scholar]
- Nazeeruddin, M.K.; Kay, A.; Rodicio, I.; Humphry-Baker, R.; Muller, E.; Liska, P.; Vlachopoulos, N.; Gratzel, M. Conversion of light to electricity by cis-X2(dcbpy)2Ru(II) CT sensitizers on nanocrystalline TiO2 electrodes. J. Am. Chem. Soc 1993, 115, 6382–6390. [Google Scholar]
- Fang, Y.Q.; Taylor, N.J.; Laverdiere, F.; Hanan, G.S.; Loiseau, F.; Nastasi, F.; Campagna, S.; Nierengarten, H.; Leize-Wagner, E.; van Dorsselae, A. Ruthenium(II) complexes with improved photophysical properties base on planar 4′-(2-Pyrimidinyl)-2,2′,6′,2″-terpyridine ligands. Inorg. Chem 2007, 46, 2854–2863. [Google Scholar]
- Constable, E.C. Expanded ligands-An assembly principle for supramolecular chemistry. Coord. Chem. Rev 2008, 252, 842–855. [Google Scholar]
- Sauvage, J.P.; Collin, J.P.; Chambron, J.C.; Guillerez, S.; Coudret, C.; Balzani, V.; Barigelletti, F.; de Cola, L.; Flamigni, L. Ruthenium(II) and Osmium(II) bis(terpyridine) complexes in covalently-linked multicomponent systems: Synthesis, electrochemical behavior, absorption spectra, and photochemical and photophysical properties. Chem. Rev 1994, 94, 993–1019. [Google Scholar]
- Beres, J.E.; Constable, E.C.; Housecroft, C.E.; Neuburger, M.; Schaffner, S. A pyrazolyl-terminated 2,2′:6′,2″-terpyridine ligand: Iron(II), Ruthenium(II) and Palladium(II) complexes of 4′-(3,5-dimethylpyrazol-1-yl)-2,2′:6′,2″-terpyridine. Polyhedron 2008, 27, 2395–2401. [Google Scholar]
- Kawanishi, Y.; Kitamura, N.; Tazuke, S. Dependence of spectroscopic, electrochemical, and excited-state properties of tris-chelate ruthenium(II) complexes on ligand structure. Inorg. Chem 1989, 28, 2968–2975. [Google Scholar]
- Shen, Y.; Maliwal, B.P.; Lakowicz, J.R. Red-emitting Ru(II) metal-ligand complexes. J. Fluoresc 2003, 13, 163–168. [Google Scholar]
- Strouse, G.F.; Schoonover, J.R.; Duesing, R.; Boyde, S.; Jones, W.E.; Meyer, T.J. Influence of electronic delocalization in metal to ligand charge transfer excited states. Inorg. Chem 1995, 34, 473–487. [Google Scholar]
- Anderson, P.A.; Deacon, G.B.; Haarman, K.H.; Keene, F.R.; Meyer, T.J.; Reitsma, D.A.; Shelton, B.W.; Strouse, G.F.; Thomas, N.C.; Treadway, J.A.; et al. Designed synthesis of mononuclear tris(heteroleptic) ruthenium complexes containing bidentate polypyridyl ligands. Inorg. Chem 1995, 34, 6145–6157. [Google Scholar]
- Wacholtz, W.F.; Aeurbach, R.A.; Schmehl, R.H. Independent control charge transfer and metal centered excited states in mixed ligand polypyridine ruthenium(II) complexes via specific ligand design. Inorg. Chem 1986, 25, 227–234. [Google Scholar]
- Anderson, P.A.; Strouse, G.F.; Treadway, J.A.; Keene, F.R.; Meyer, T.J. Black MLCT absorbers. Inorg. Chem 1994, 33, 3863–3864. [Google Scholar]
- Kalyanasundaram, K.; Nazeeruddin, M.K.; Gratzel, M.; Viscardi, G.; Savarino, P.; Barni, E. Synthesis and photophysical characterization of highly luminescent complexes of ruthenium(II) containing 4,4′-di (p-carboxyphenyl)-2,2′-bipyridine. Inorg. Chem. Acta 1992, 198–200, 831–839. [Google Scholar]
- Demas, J.N.; Harris, E.W.; McBride, R.P.J. Energy transfer from luminescent transition metal complexes to oxygen. J. Am. Chem. Soc 1977, 99, 3547–3551. [Google Scholar]
- Wolfgang, S.; Gafney, H.D. Quenching of Ru(bpy)3 2+ ionically bound to porous Vycor glass by O2, N2O and SO2. J. Phys. Chem 1983, 87, 5395–5401. [Google Scholar]
- Vyas, P.; Bhatt, A.K.; Ramachandraiah, G.; Bedekar, A.V. Environmentally benign chlorination and bromination of aromatic amines, hydrocarbons and naphthols. Tetrahedron Lett 2003, 44, 4085–4088. [Google Scholar]
- Evans, I.P.; Spencer, A.; Wilkinson, G. Dichlorotetrakis(dimethyl sulphoxide) ruthenium(II) and its use as a source material for some new Ruthenium(II) complexes. J. Chem. Soc. Dalton Trans 1973. [Google Scholar] [CrossRef]
- Mitsopoulou, C.A.; Veroni, I.; Philippopoulos, A.I.; Falaras, P. Synthesis, characterization and sensitization properties of two novel mono and bis carboxyl-dipyrido-phenazine ruthenium(II) charge transfer complexes. J. Photochem. Photobiol. A 2007, 191, 6–12. [Google Scholar]
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Adeloye, A.O.; Olomola, T.O.; Adebayo, A.I.; Ajibade, P.A. A High Molar Extinction Coefficient Bisterpyridyl Homoleptic Ru(II) Complex with trans-2-Methyl-2-butenoic Acid Functionality: Potential Dye for Dye-Sensitized Solar Cells. Int. J. Mol. Sci. 2012, 13, 3511-3526. https://doi.org/10.3390/ijms13033511
Adeloye AO, Olomola TO, Adebayo AI, Ajibade PA. A High Molar Extinction Coefficient Bisterpyridyl Homoleptic Ru(II) Complex with trans-2-Methyl-2-butenoic Acid Functionality: Potential Dye for Dye-Sensitized Solar Cells. International Journal of Molecular Sciences. 2012; 13(3):3511-3526. https://doi.org/10.3390/ijms13033511
Chicago/Turabian StyleAdeloye, Adewale O., Temitope O. Olomola, Akinbulu I. Adebayo, and Peter A. Ajibade. 2012. "A High Molar Extinction Coefficient Bisterpyridyl Homoleptic Ru(II) Complex with trans-2-Methyl-2-butenoic Acid Functionality: Potential Dye for Dye-Sensitized Solar Cells" International Journal of Molecular Sciences 13, no. 3: 3511-3526. https://doi.org/10.3390/ijms13033511