Influence of axial and peripheral ligands on the electronic structure of titanium phthalocyanines

Journal of Physical Chemistry C

Volumn 117, Issue 9, 2013, Pages 4410-4420

  Pickup, David F ^a,b   Zegkinoglou, Ioannis ^c,d   Ballesteros, Beatriz ^e   Ganivet, Carolina R ^e   Garcia Lastra J M ^a,b,f   Cook, Peter L ^g   Johnson, Phillip S ^c   Rogero, Celia ^a,h   De Groot, Frank ⁱ   Rubio, Angel ^a,b   De La Torre, Gema ^e   Ortega, J Enrique ^a,b,h   Himpsel, F J ^c  

^a CENTRO MIXTO CSIC UPV EHU   (Spain)

^b UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^c Wisconsin Electric Machines and Power Electronics Consortium   (United States)

^d LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

^e UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^f TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^g UNIVERSITY OF WISCONSIN SUPERIOR   (United States)

^h DONOSTIA INTERNATIONAL PHYSICS CENTER DIPC   (Spain)

ⁱ UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BIDENTATE COMPLEXES; CRYSTAL FIELDS; DENSITY FUNCTIONAL THEORIES (DFT); FRONTIER ORBITALS; MOLECULAR CHANGES; MULTIPLET STRUCTURES; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; VALENCE ELECTRON;

BINDING ENERGY; DENSITY FUNCTIONAL THEORY; ELECTRONIC STRUCTURE; NITROGEN COMPOUNDS; PHENOLS; PHOTOELECTRON SPECTROSCOPY; THREE DIMENSIONAL COMPUTER GRAPHICS; TITANIUM; X RAY ABSORPTION SPECTROSCOPY;

LIGANDS;

EID: 84874925062     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp3117853     Document Type: Article

References (65)

1. Ning, Z. J.; Fu, Y.; Tian, H. Improvement of Dye-Sensitized Solar Cells: What We Know and What We Need to Know Energy Environ. Sci. 2010, 3, 1170-1181
2. Helgesen, M.; Soundergaard, R.; Krebs, F. C. Advanced Materials and Processes for Polymer Solar Cell Devices J. Mater. Chem. 2010, 20, 36-60
3. Kippelen, B.; Bredas, J. L. Organic Photovoltaics Energy Environ. Sci. 2009, 2, 251-261
4. Walker, B.; Kim, C.; Nguyen, T. C. Small Molecule Solution-Processed Bulk Heterojunction Solar Cells Chem. Mater. 2011, 23, 470-482
5. Hagfeldt, A.; Boschloo, G.; Sun, L. C.; Kloo, L.; Pettersson, H. Dye-Sensitized Solar Cells Chem. Rev. 2010, 110, 6595-6663
6. Cook, P. L.; Liu, X.; Yang, W.; Himpsel, F. J. X-ray Absorption Spectroscopy of Biomimetic Dye Molecules for Solar Cells J. Chem. Phys. 2009, 131, 194701
7. Cook, P. L.; Johnson, P. L.; Liu, X.; Chin, A. L.; Himpsel, F. J. Radiation Damage in Biomimetic Dye Molecules for Solar Cells J. Chem. Phys. 2009, 131, 214702
8. Garcia-Lastra, J. M.; Cook, P. L.; Himpsel, F. J.; Rubio, A. Communication: Systematic Shifts of the Lowest Unoccupied Molecular Orbital Peak in X-ray Absorption for a Series of 3d Metal Porphyrins J. Chem. Phys. 2010, 133, 151103
9. Cook, P. L.; Yang, W.; Liu, X.; Garcia-Lastra, J. M.; Rubio, A.; Himpsel, F. J. Unoccupied States in Cu and Zn Octaethyl-porphyrin and Phthalocyanine J. Chem. Phys. 2011, 134, 204707
10. González-Moreno, R.; Cook, P. L.; Zegkinoglou, I.; Liu, X.; Johnson, P.; Yang, W.; Ruther, R.; Hamers, R. J.; Tena-Zaera, R.; Himpsel, F. J.; Ortega, J. E.; Rogero, C. Attachment of Protoporphyrin Dyes to Nanostructured ZnO Surfaces: Characterization by Near Edge X-ray Absorption Fine Structure Spectroscopy J. Phys. Chem. C 2011, 115, 18195-18201
11. Himpsel, F. J.; Cook, P. L.; de la Torre, G.; Garcia-Lastra, J. M.; González-Moreno, R.; Guo, J.-H.; Hamers, R. J.; Kronawitter, C. X.; Johnson, P. S.; Ortega, J. E.; Pickup, D.; Ragoussi, M.-E.; Rogero, C.; Rubio, A.; Ruther, R. E.; Vayssieres, L.; Yang, W.; Zegkinoglou, I. Design of Solar Cell Materials via Soft X-ray Spectroscopy. J. Electron Spectrosc. Relat. Phenom., published online Oct 22, 2012, http://dx.doi.org/10.1016/j.elspec.2012. 10.002.
12. Lai, S. L.; Chan, M. Y.; Fung, M. K.; Lee, C. S.; Lee, S. T. Copper Hexadecafluorophthalocyanine and Copper Phthalocyanine as a Pure Organic Connecting Unit in Blue Tandem Organic Light.Emitting Devices J. Appl. Phys. 2007, 101, 014509
13. Li, J. F.; Su, S. H.; Hwang, K. S.; Yokoyama, M. Enhancing the Contrast and Power Efficiency of Organic Light-Emitting Diodes Using CuPc/TiOPc as an Anti-Reflection Layer J. Phys. D: Appl. Phys. 2007, 40, 2435-2439
14. Ragoussi, M. E.; Cid, J. J.; Yum, J. H.; de la Torre, G.; Di Censo, D.; Grätzel, M.; Nazeeruddin, M. K.; Torres, T. Carboxyethynyl Anchoring Ligands: A Means to Improving the Efficiency of Phthalocyanine-Sensitized Solar Cells Angew. Chem., Int. Ed. 2012, 51, 4375-4378
15. 2 Surface Surf. Sci. 2003, 539, 37-48
16. Dufour, G.; Poncey, C.; Rochet, F.; Roulet, H.; Iacobucci, S.; Sacchi, M.; Yubero, F.; Motta, N.; Piancastelli, M. N.; Sgarlata, A.; De Crescenzi, M. Metal Phthalocyanines (MPc, M = Ni, Cu) on Cu(001) and Si(001) Surfaces Studied by XPS, XAS and STM J. Electron Spectrosc. Relat. Phenom. 1995, 76, 219-224
17. Petraki, F.; Peisert, H.; Ayguel, U.; Latteyer, F.; Uihlein, J.; Vollmer, A.; Chasse, T. Electronic Structure of FePc and Interface Properties on Ag(111) and Au(100) J. Phys. Chem. C 2012, 116, 11110-11116
18. Yoshida, H.; Tsutsumi, K.; Sato, N. Unoccupied Electron States of 3d-Transition Metal Phthalocyanines (MPc: M = Mn, Fe, Co, Ni, Cu and Zn) Studied by Inverse Photoemission Spectroscopy J. Electron Spectrosc. Relat. Phenom. 2001, 121, 83-91
19. Krasnikov, S. A.; Preobrajenski, A. B.; Sergeeva, N. N.; Brzhezinskaya, M. M.; Nesterov, M. A.; Cafolla, A. A.; Senge, M. O.; Vinogradov, A. S. Electronic Structure of Ni(II) Porphyrins and Phthalocyanine Studied by Soft X-ray Absorption Spectroscopy Chem. Phys. 2007, 332, 318-324
20. Alfredsson, Y.; Rensmo, H.; Sandell, A.; Siegbahn, H. Electronic Structure of Thin Film TiOPc Studied by means of X-ray Absorption and Photoelectron Spectroscopies J. Electron Spectrosc. Relat. Phenom. 2009, 174, 50-54
21. Zhang, Y.; Wang, S.; Demasi, A.; Reid, I.; Piper, L. F. J.; Matsuura, A. Y.; Downes, J. E.; Smith, K. E. Soft X-ray Spectroscopy Study of Electronic Structure in the Organic Semiconductor Titanyl Phthalocyanine (TiOPc) J. Mater. Chem. 2008, 18, 1792-1798
22. 60 Heterojunctions: Band-Edge Offsets and Photovoltaic Device Performance J. Phys. Chem. C 2008, 112, 3142-3151
23. Nishi, T.; Kanai, K.; Ouchi, Y.; Willis, M. R.; Seki, K. Evidence for the Atmospheric p -Type Doping of Titanyl Phthalocyanine Thin Film by Oxygen Observed as the Change of Interfacial Electronic Structure Chem. Phys. Lett. 2005, 414, 479-482
24. Harada, Y.; Tokushima, T.; Takata, Y.; Kamakura, N.; Takeuchi, T.; Kobayashi, K.; Shirota, Y.; Shin, S. Intermolecular Interaction by Apical Oxygen in Titanyl Phthalocyanine Jpn. J. Appl. Phys. 2005, 44, L1147-L1149
25. Zhang, Y. F.; Wang, S. C.; Learmonth, T.; Plucinski, L.; Matsuura, A. Y.; Bernardis, S.; O'Donnell, C.; Downes, J. E.; Smith, K. E. Electronic Excitations in Vanadium Oxide Phthalocyanine Studied via Resonant Soft X-ray Emission and Resonant Inelastic X-ray Scattering Chem. Phys. Lett. 2005, 413, 95-99
26. Zhang, Y. F.; Learmonth, T.; Wang, S. C.; Matsuura, A. Y.; Downes, J. E.; Plucinski, L.; Bernardis, S.; O'Donnell, C.; Smith, K. E. Electronic Structure of the Organic Semiconductor Titanyl Phthalocyanine (TiOPc) J. Mater. Chem. 2007, 17, 1276-1283
27. Fukagawa, H.; Yamane, H.; Kera, S.; Okudaira, K. K.; Ueno, N. UPS Fine Structures of Highest Occupied Band in Vanadyl-Phthalocyanine Ultrathin Film J. Electron Spectrosc. Relat. Phenom. 2005, 144, 475-477
28. Thavasi, V.; Renugopalakrishnan, V.; Jose, R.; Ramakrishna, S. Controlled Electron Injection and Transport at Materials Interfaces in Dye Sensitized Solar Cells Mater. Sci. Eng. R 2009, 63, 81-99
29. Walter, M. J.; Rudine, A. B.; Wamser, C. C. Porphyrins and Phthalocyanines in Solar Photovoltaic Cells J. Porphyrins Phthalocyanines 2010, 14, 759-792
30. Bessho, T.; Zakeeruddin, S. M.; Yeh, C.-Y.; Wei-Guang Diau, E.; Grätzel, M. Highly Efficient Mesoscopic Dye-Sensitized Solar Cells Based on Donor-Acceptor-Substituted Porphyrins Angew. Chem., Int. Ed. 2010, 49, 6646-6649
31. Pozzi, G.; Quici, S.; Raffo, M. C.; Bignozzi, C. A.; Caramori, S.; Orlandi, M. Fluorous Molecules for Dye-Sensitized Solar Cells: Synthesis and Photoelectrochemistry of Unsymmetrical Zinc Phthalocyanine Sensitizers with Bulky Fluorophilic Donor Groups J. Phys. Chem. C 2011, 115, 3777-3788
32. Barthel, M.; Dini, D.; Vagin, S.; Hanack, M. An Easy Route for the Synthesis of New Axially Substituted Titanium(IV) Phthalocyanines Eur. J. Org. Chem. 2002, 22, 3756-3762
33. Barthel, M.; Hanack, M. Axially Substituted Titanium(IV) Phthalocyanines J. Porphyrins Phthalocyanines 2000, 4, 635-638
34. 60 Supramolecular Dyad Tetrahedron 2006, 62, 2097-2101
35. h (Octahedral) Symmetry Phys. Rev. B 1990, 41, 928-937
36. 2,3 X-ray Absorption Spectra of Early 3d Transition Elements Phys. Rev. B 2010, 82, 205104
37. Johnson, P. S.; Cook, P. L.; Liu, X.; Yang, W.; Bai, Y.; Abbott, N. L.; Himpsel, F. J. Universal Mechanism for Breaking Amide Bonds by Ionizing Radiation J. Chem. Phys. 2011, 135, 044702
38. Sodhi, R. N. S.; Brion, C. E. Reference Energies for Inner Shell Electron Energy-Loss Spectroscopy J. Electron Spectrosc. Relat. Phenom. 1984, 34, 363-372
39. Velde, G. T.; Bickelhaupt, F. M.; Baerends, E. J.; Guerra, C. F.; Van Gisbergen, S.J. A.; Snijders, J. G.; Ziegler, T. Chemistry with ADF J. Comput. Chem. 2001, 22, 931-967
40. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-3868
41. Vosko, S. H.; Wilk, L.; Nusair, M. Accurate Spin-Dependent Electron Liquid Correlation Energies for Local Spin Density Calculations: A Critical Analysis Can. J. Phys. 1980, 58, 1200-1211
42. Stavitski, E.; de Groot, F. M. F. The CTM4XAS Prgram for EELS and XAS Spectral Shape Analysis of Transition Metal L Edges Micron 2010, 41, 687-694
43. Cowan, R. D. The Theory of Atomic Structure and Spectra; University of California Press: Berkeley, CA, 1981.
44. Butler, P. H. Point Group Symmetry, Applications, Methods and Tables; Plenum Press: New York, 1981.
45. Thole, B. T.; van der Laan, G.; Butler, P. H. Spin-Mixed Ground State of Fe Phthalocyanine and the Temperature-Dependent Branching Ratio in X-ray Absorption Spectroscopy Chem. Phys. Lett. 1988, 149, 295-299
46. 2 and Some Other Rare-Earth Compounds Phys. Rev. B 1991, 43, 854-859
47. Hiller, W.; Strahle, J.; Kobel, W.; Hancak, M. Polymorphie, Leitfahigkeit und Kristallstrukturen von Oxo-phthalocyaninato-titan(IV) Z. Kristallogr. 1982, 159, 173-183
48. Hoshi, H.; Yamada, T.; Ishikawa, K.; Takezoe, H.; Fukuda, A. Electric Quadrupole Second-Harmonic Generation Spectra in Epitaxial Vanadyl and Titanyl Phthalocyanine Films Grown by Molecular-Beam Epitaxy J. Chem. Phys. 1997, 107, 1687-1691
49. Norton, J. E.; Bredas, J.-L. Theoretical Characterization of Titanyl Phthalocyanine as a p -Type Organic Semiconductor: Short Intermolecular π-π Interactions Yield Large Electronic Couplings and Hole Transport Bandwidths J. Chem. Phys. 2008, 128, 034701
50. Gouterman, M.; Wagniere, G. H.; Snyder, L. C. Spectra of Porphyrins: Part II. Four Orbital Model J. Mol. Spectrosc. 1963, 11, 108-127
51. McHugh, A. J.; Gouterman, M.; Weiss, C. Porphyrins XXIV. Energy, Oscillator Strength, and Zeeman Splitting Calculations (SCMO-Cl) for Phthalocyanine, Porphyrins, and Related Ring Systems Theor. Chim. Acta 1972, 24, 346-370
52. Schaffer, A. M.; Gouterman, M.; Davidson, E. R. Porphyrins XXVIII. Extended Huckel Calculations on Metal Phthalocyanines and Tetrazaporphins Theor. Chim. Acta 1973, 30, 9-30
53. Chen, J. G. NEXAFS Investigations of Transition Metal Oxides, Nitrides, Carbides, Sulfides and Other Interstitial Compounds Surf. Sci. Rep. 1997, 30, 1-152
54. 3: Importance of Multiplet Coupling and Band Structure Phys. Rev. B 2010, 81, 125121
55. Swarbrick, J. C.; Kvashnin, Y.; Schulte, K.; Seenivasan, K.; Lamberti, C.; Glatzel, P. Ligand Identification in Titanium Complexes Using X-ray Valence-to-Core Emission Spectroscopy Inorg. Chem. 2010, 49, 8323-8332
56. Himpsel, F. J.; Karlsson, U. O.; McLean, A. B.; Terminello, L. J.; de Groot, F. M. F.; Abbate, M.; Fuggle, J. C.; Yarmoff, J. A.; Thole, B. T.; Sawatzky, G. A. Fine Structure of the Ca 2 p X-ray Absorption Edge for Bulk Compounds, Surfaces, and Interfaces Phys. Rev. B 1991, 43, 6899-6907
57. Hasselstrom, J.; Fohlisch, A.; Denecke, R.; Nilsson, A.; de Groot, F. M. F. Crystal-field Splitting in Coadsorbate Systems: c (2 × 2) CO/K/Ni(100) Phys. Rev. B 2000, 62, 11192-11196
58. van der Laan, G.; Kirkman, I. W. The 2p Absorption Spectra of 3d Transition Metal Compounds in Tetrahedral and Octahedral Geometry J. Phys.: Condens. Matter 1992, 4, 4189-4204
59. Ballhausen, C. J. Introduction to Ligand Field Theory; McGraw-Hill: New York, 1962.
60. Hocking, R. K.; Wasinger, E. C.; Yan, Y.-L.; de Groot, F. M. F.; Walker, F. A.; Hodgson, K. O.; Hedman, B.; Solomon, E. I. Fe L-Edge X-ray Absorption Spectroscopy of Low-Spin Heme Relative to Non-heme Fe Complexes: Delocalization of Fe d-Electrons into the Porphyrin Ligand J. Am. Chem. Soc. 2007, 129, 113-125
61. Piper, L. F. J.; Cho, S. W.; Zhang, Y.; DeMasi, A.; Smith, K. E.; Matsuura, A. Y.; McGuinness, C. Soft X-ray Spectroscopy Study of the Element and Orbital Contributions to the Electronic Structure of Copper Hexadecafluoro-phthalocyanine Phys. Rev. B 2010, 81, 045201
62. Zhang, W.; Fang, Z.; Su, M. J.; Saeys, M.; Liu, B. A Triphenylamine-Based Conjugated Polymer with Donor-Acceptor Architecture as Organic Sensitizer for Dye-Sensitized Solar Cells Macromol. Rapid Commun. 2009, 30, 1533-1537
63. Chen, B.-S.; Chen, D.-Y.; Chen, C.-L.; Hsu, C.-W.; Hsu, H.-C.; Wu, K.-L.; Liu, S.-H.; Chou, P. T.; Chi, Y. Donor-Acceptor Dyes with Fluorine Substituted Phenylene Spacer for Dye-Sensitized Solar Cells J. Mater. Chem. 2011, 21, 1937-1945
64. Wu, S.-L.; Lu, H.-P.; Yu, H.-T.; Chuang, S.-H.; Chiu, C.-L.; Lee, C.-W.; Diau, E. W-G.; Yeh, C.-Y. Design and Characterization of Porphyrin Sensitizers with a Push-Pull Framework for Highly Efficient Dye-Sensitized Solar Cells Energy Environ. Sci. 2010, 3, 949-955
65. Yella, A.; Lee, H.-W.; Tsao, H. N.; Yi, C.; Chandiran, a. K.; Nazeeruddin, M. K.; Diau, E. W.-G.; Yeh, C.-Y.; Zakeeruddin, S. M.; Grätzel, M. Porphyrin-Sensitized Solar Cells with Cobalt (II/III)-Based Redox Electrolyte Exceed 12% Efficiency Science 2011, 334, 629-634