A high molar extinction coefficient mono-anthracenyl bipyridyl heteroleptic ruthenium(II) complex: Synthesis, photophysical and electrochemical properties

Molecules

Volumn 16, Issue 6, 2011, Pages 4615-4631

  Adeloye, Adewale O ^a   Ajibade, Peter A ^a  

^a UNIVERSITY OF FORT HARE   (South Africa)

Author keywords

Bipyridine; Extended p bond conjugation; Molar extinction coefficient; Molecular aggregation; Ru(II) complex; Spectroscopy

Indexed keywords

2,2' BIPYRIDINE; ANTHRACENE DERIVATIVE; LIGAND; PHOTOSENSITIZING AGENT; RUTHENIUM;

ARTICLE; CHEMISTRY; ELECTROCHEMISTRY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; SYNTHESIS; X RAY PHOTOELECTRON SPECTROSCOPY;

2,2'-DIPYRIDYL; ANTHRACENES; ELECTROCHEMISTRY; LIGANDS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PHOTOCHEMISTRY; PHOTOELECTRON SPECTROSCOPY; PHOTOSENSITIZING AGENTS; RUTHENIUM; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 79959625137     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16064615     Document Type: Article

References (41)

1. 2 solar cells with chlorophyll derivatives and related natural porphyrins. J. Phys. Chem. 1993, 117, 6272-6277.
2. 2 films by ruthenium phthalocyanines. Chem. Commun. 1998, 719-720. (Pubitemid 128675364)
3. 2 semiconductor electrode with xanthene dyes. Chem. Lett. 1998, 753-754.
4. Ferrere, S.; Zaban, A.; Gregg, B.A. Dye sensitization of nanocrystalline Tin oxide by perylene derivatives. J. Phys. Chem. B 1997, 101, 4490-4493. (Pubitemid 127596242)
5. 2 films. Nature 1991, 353, 737-740. (Pubitemid 21912607)
6. 2 electrodes. J. Am. Chem. Soc. 1993, 115, 6382-6390.
7. Hara, K.; Sugihara, H.; Singh, L.P.; Islam, A.; Kator, R.; Yanagida, M.; Sayama, K.; Murata, S.; Arakawa, H. New Ru(II) phenanthroline complex photosensitizers having different number of carboxyl groups for dye-sensitized solar cells. J. Photochem. Photobiol. A-Chem. 2001, 145, 117-122. (Pubitemid 33376873)
8. Nazeeruddin, Md.K.; Bessho, T.; Le Cevey; Ito, S.; Klein, C.; De Angelis, F.; Fantacci, S.; Comte, P.; Liska, P.; Imai, H.; Grätzel, M. A high molar extinction coefficient charge transfer sensitizer and its application in dye-sensitized solar cells. J. Photochem. Photobiol. A-Chem. 2007, 185, 331-337.
9. Pearson, P.; Bond, A.M.; Deacon, G.B.; Forsyth, C.; Spiccia, L. Synthesis and characterization of bis(2,2'-bipyridine)(4-carboxy-4'-(pyrid-2- ylmethylamido)-2,2'-bipridine) ruthenium(II) dihexafluorophosphate): Comparison of spectroelectro-chemical properties with related complexes. Inorg. Chim. Acta 2008, 361, 601-612.
10. Funaki, T.; Yanagida, M.; Onozawa-Komatsuzaki, N.; Kawanishi, Y.; Kasuga, K.; Sugihara, H. Ruthenium(II) complexes with p expanded ligands having phenylene-ethynylene moiety as sensitizers for dye-sensitized solar cells. Solar Energy Mat. Solar Cells 2009, 93, 729-732.
11. Li, C.; Yang, X.; Chen, R.; Pan, J.; Tian, H.; Zhu, H.; Wang, X.; Hagfeldt, A.; Sun, L. Anthraquinone dyes as photosensitizers for dye-sensitized solar cells. Solar Energy Mat. Solar Cells 2007, 91, 1863-1871. (Pubitemid 47385156)
12. Wang, X.F.; Fuji, R.; Ito, S.; Koyama, Y.; Yamano, Y.; Ito, M.; Kitamura, T.; Yanagida, S. Dye-sensitized solar cells using retinoic acid and carotenoic acids: Dependence of performance on the conjugation length and the dye concentration. Chem. Phys. Lett. 2005, 416, 1-6.
13. Song, A.; Zhang, H.; Zhang, M.; Shen, T. Photophysical properties of polyads containing a fluorescein moiety. Dyes Pigments 1999, 42, 149-158.
14. Mosurkal, R.; He, J.; Yang, K.; Samuelson, L.A.; Kumar, J. Organic photosensitizers with catechol groups for dye-sensitized photovoltaics J. Photochem. Photobiol. A-Chem. 2004, 168, 191-196.
15. Wang, P.; Zakeeruddin, S.M.; Moser, J.E.; Humphry-Baker, R.; Comte, P.; Aranyos, V.; Hagfeldt, A.; Nazeeruddin, M.K.; Gratzel, M. Stable new sensitizer with improved light harvesting for nanocrystalline dye-sensitized solar cells. Adv. Mater. 2004, 16, 1806-1811.
16. Chen, C.Y.; Wu, S.J.; Wu, C.G.; Chen, J.G.; Ho, K.C. A Ruthenium complex with superhigh light harvesting capacity for dye-sensitized solar cells. Angew. Chem. Int. Ed. 2006, 45, 5822-5825.
17. Leroy-Lhez, S.; Belin, C.; D'aleo, A.; Williams, R.M.; De Cola, L.; Fages, F. Extending excited-state lifetimes by interchromophoric triplet-state equilibration in a pyrene-Ru(II) diimine dyad system. Supramol. Chem. 2003, 15, 627-637. (Pubitemid 37373966)
18. Juris, A.; Balzani, V.; Barigelletti, F.; Campagna, S.; Belser, P.; Zelewsky, A.V. Ruthenium(II) polypyridine complexes: Photophysics, photochemistry, electrochemistry, and chemiluminescence. Coord. Chem. Rev. 1988, 84, 85-277.
19. Juris, A.; Campagna, S.; Balzani, V.; Gremaud, G.; Zelewsky, A.V. Absorption spectra, luminescence properties and electrochemical behaviuor of tris-heteroleptic ruthenium(II) polypyridine complexes. Inorg. Chem. 1988, 27, 3652-3655.
20. Goze, C.; Kozlov, D.V.; Castellano, F.N.; Suffert, J.; Ziessel, R. Synthesis of bipyridine and terpyridine based ruthenium metallosynthons for grafting of multiple pyrene auxiliaries. Tetrahedron 2003, 44, 8713-8716. (Pubitemid 37324785)
21. 2 solar cells. Chem. Commun. 2006, 2460-2462. (Pubitemid 43880307)
22. Kukrek, A.; Wang, D.; Hou, Y.; Zong, R.; Thummel, R. Photosensitizers containing the 1,8-naphthyridyl moiety and their use in dye-sensitized solar cells. Inorg. Chem. 2006, 45, 10131-10317.
23. 2 with cis-bis(4-carboxy-2-[2'-(4'-carboxypyridyl)] quinoline) bis(thiocyanato-N) ruthenium(II). Inorg. Chem. 2003, 42, 7921-7931.
24. Sauve, G.; Cass, M.E.; Coia, G.; Doig, S.J.; Lauermann, I.; Pomykal, K.E.; Lewis, N.S. Dye-sensitization of nanocrystalline titanium dioxide with osmium and ruthenium polypyridyl complexes. J. Phys. Chem. 2000, 104, 6831-6836.
25. Argazzi, R.; Bignozzi, C.A.; Heimer, T.A.; Castellano, F.N.; Meyer, G.J. Enhanced spectral sensitivity from Ru(II) polypyridyl photovoltaic devices. Inorg. Chem. 1994, 33, 5741-5749.
26. 2 interfaces. J. Phys. Chem. A 2000, 104, 4256-4262.
27. Polo, A.S.; Itokazu, M.K.; Iha, N.Y.M. Metal complex sensitizers in dye-sensitized solar cells. Coord. Chem. Rev. 2004, 248, 1343-1361.
28. Adeloye, A.O.; Ajibade, P.A. Synthesis and characterization of a heteroleptic Ru(II) complex of phenanthroline containing oligo-anthracenyl carboxylic acid moieties. Int. J. Mol. Sci. 2010, 11, 3158-3176.
29. Adeloye, A.O.; Ajibade, P.A. Synthesis and characterization of a Ru(II) complex with functionalized phenanthroline ligands having single-double linked anthracenyl and 1-methoxybuten- 3-yne moieties. Molecules 2010, 15, 7570-7581.
30. 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. (Pubitemid 36549135)
31. 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 1973, 204-208.
32. 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-Chem. 2007, 191, 6-12.
33. Gunzler, H.; Gremlich, H. IR Spectroscopy-An Introduction; Wiley-VCH Verlag GmbH: Weinheim, Germany, 2002.
34. Chen, C.Y.; Wu, S.J.; Li, J.Y.; Wu, C.G.; Chen, J.G.; Ho, K.C. A new route to enhance the light harvesting capability of ruthenium complexes for dye-sensitized solar cells. Advan. Mater. 2007, 19, 3888-3891.
35. Adeloye, A.O.; Ajibade, P.A. Synthesis, characterization and preliminary investigation of the electro redox properties of anthracenyl-functionalized terpyridyl ligands. Tetrahedron Lett. 2011, 52, 274-277.
36. Imatori, H.; Umeyama, T.; Ito, S. Large pi-aromatic molecules as potential sensitizers for highly efficient dye-sensitized solar cells. Acc. Chem. Res. 2009, 42, 1809-1818.
37. Crosby, G.A.; Watts, R.J.; Carstens, D.H.W. Inversion of excited state of transition-metal complexes. Science 1970, 170, 1195-1196.
38. Henderson, L.J., Jr.; Fronczek, F.R.; Cherry, W.R. Selective perturbation of ligand field excited states in polypyridine ruthenium(II) complexes. J. Am. Chem. Soc. 1984, 106, 5876-5879.
39. Staniszewski, A.; Heuer, W.B.; Meyer, G.J. High-extinction ruthenium compounds for sunlight harvesting and hole transport. Inorg. Chem. 2008, 47, 7062-7064.
40. Nalwa, H.S.; Shirk, J.S. In Phthalocyanines, Properties and Applications; Leznoff, C.C., Lever, A.B.P., Eds.; VCH: New York, NY, USA, 1996; Volume 4, pp. 79-182.
41. Roundhill, D.M. Photochemistry and Photophysics of Metal Complexes; Plenum Address: New York, NY, USA, 1993.