Functionalized Porphyrins on an Atomically Defined Oxide Surface: Anchoring and Coverage-Dependent Reorientation of MCTPP on Co3O4(111)

Journal of Physical Chemistry Letters

Volumn 7, Issue 3, 2016, Pages 555-560

  Werner, Kristin ^a   Mohr, Susanne ^a   Schwarz, Matthias ^a   Xu, Tao ^a   Amende, Max ^a   Döpper, Tibor ^a   Görling, Andreas ^a   Libuda, Jörg ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; CARBOXYLATION; COBALT; MOLECULAR ORIENTATION;

ADSORPTION GEOMETRIES; BIDENTATE CARBOXYLATES; FUNCTIONALIZED; MOLECULAR TILTING ANGLES; OXIDE SURFACE; TETRAPHENYL PORPHYRINS; TILTING ANGLE; TIME-RESOLVED INFRARED;

DENSITY FUNCTIONAL THEORY;

EID: 84957593968     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/acs.jpclett.5b02784     Document Type: Article

References (40)

1. 2 Solar Cell Coord. Chem. Rev. 2004, 248, 1363-1379 10.1016/j.ccr.2004.01.007
2. 2 Surfaces with Different Orientations: A Photophysical, Photovoltaic, and Theoretical Investigation J. Phys. Chem. A 2014, 118, 3410-3418 10.1021/jp412609k
3. Jurow, M.; Schuckman, A. E.; Batteas, J. D.; Drain, C. M. Porphyrins as Molecular Electronic Components of Functional Devices Coord. Chem. Rev. 2010, 254, 2297-2310 10.1016/j.ccr.2010.05.014
4. Chen, J.; Sheng, Y.; Ko, S.; Liu, L.; Han, H.; Li, X. Push-pull Porphyrins with Different Anchoring Group Orientations for Fully Printable Monolithic Dye-sensitized Solar Cells with Mesoscopic Carbon Counter Electrodes New J. Chem. 2015, 39, 5231-5239 10.1039/C5NJ00569H
5. Hart, A. S.; KC, C. B.; Gobeze, H. B.; Sequeira, L. R.; DSouza, F. Porphyrin-sensitized Solar Cells: Effect of Carboxyl Anchor Group Orientation on the Cell Performance ACS Appl. Mater. Interfaces 2013, 5, 5314-23 10.1021/am401201q
6. Rochford, J.; Chu, D.; Hagfeldt, A.; Galoppini, E. Tetrachelate Porphyrin Chromophores for Metal Oxide Semiconductor Sensitization: Effect of the Spacer Length and Anchoring Group Position J. Am. Chem. Soc. 2007, 129, 4655-4665 10.1021/ja068218u
7. 2(110) and ZnO(11-20) Surfaces J. Phys. Chem. C 2012, 116, 23921-23930 10.1021/jp307454y
8. Dubois, L. H.; Zegarski, B. R.; Nuzzo, R. G. Molecular ordering of organosulfur compounds on Au(111) and Au(100): Adsorption from Solution and in Ultrahigh Vacuum J. Chem. Phys. 1993, 98, 678 10.1063/1.464613
9. Liu, J.; Schüpbach, B.; Bashir, A.; Shekhah, O.; Nefedov, A.; Kind, M.; Terfort, A.; Wöll, C. Structural Characterization of Self-assembled Monolayers of Pyridine-terminated Thiolates on Gold Phys. Chem. Chem. Phys. 2010, 12, 4459-4472 10.1039/b924246p
10. 2(110) Prepared by In-situ Electrospray Deposition J. Chem. Phys. 2010, 132, 084703 10.1063/1.3336747
11. Gottfried, J. M. Surface Chemistry of Porphyrins and Phthalocyanines Surf. Sci. Rep. 2015, 70, 259-379 10.1016/j.surfrep.2015.04.001
12. Marbach, H. Surface-Mediated In-Situ Metalation of Porphyrins at the Solid-Vacuum Interface Acc. Chem. Res. 2015, 48, 2649-58 10.1021/acs.accounts.5b00243
13. Gu, D.; Jia, C.-J.; Weidenthaler, C.; Bongard, H.-J.; Spliethoff, B.; Schmidt, W.; Schüth, F. Highly Ordered Mesoporous Cobalt-Containing Oxides: Structure, Catalytic Properties, and Active Sites in Oxidation of Carbon Monoxide J. Am. Chem. Soc. 2015, 137, 11407-11418 10.1021/jacs.5b06336
14. Zhu, C.; Wen, D.; Leubner, S.; Oschatz, M.; Liu, W.; Holzschuh, M.; Simon, F.; Kaskel, S.; Eychmuller, A. Nickel Cobalt Oxide Hollow Nanosponges as Advanced Electrocatalysts for the Oxygen Evolution Reaction Chem. Commun. 2015, 51, 7851-7854 10.1039/C5CC01558H
15. Moro, F.; Yu Tang, S. V.; Tuna, F.; Lester, E. Magnetic Properties of Cobalt Oxide Nanoparticles Synthesised by a Continuous Hydrothermal Method J. Magn. Magn. Mater. 2013, 348, 1-7 10.1016/j.jmmm.2013.07.064
16. Heinz, K.; Hammer, L. Epitaxial Cobalt Oxide Films on Ir(100)-The Importance of Crystallographic Analyses J. Phys.: Condens. Matter 2013, 25, 173001 10.1088/0953-8984/25/17/173001
17. 4(111) Films Grown Epitaxially on Ir(100)-(1 × 1) J. Phys.: Condens. Matter 2008, 20, 265011 10.1088/0953-8984/20/26/265011
18. Hoffmann, F. M. Infrared Reflection Absorption Spectroscopy of Adsorbed Molecules Surf. Sci. Rep. 1983, 3, 107-192 10.1016/0167-5729(83)90001-8
19. Alben, J. O.; Choi, S. S.; Adler, A. D.; Caughey, W. S. Infrared Spectroscopy of Porphyrins Ann. N. Y. Acad. Sci. 1973, 206, 278-295 10.1111/j.1749-6632.1973.tb43217.x
20. Li, X. Y.; Zgierski, M. Z. Porphine Force Field: In-plane normal Modes of Free-base Porphine; Comparison with Metalloporphines and Structural Implications J. Phys. Chem. 1991, 95, 4268-4287 10.1021/j100164a020
21. Wan, J.; Wang, H.; Wu, Z.; Shun, Y. C.; Zheng, X.; Phillips, D. L. Resonance Raman Spectroscopy and Density Functional Theory Calculation Study of Photodecay Dynamics of Tetra(4-carboxyphenyl) Porphyrin Phys. Chem. Chem. Phys. 2011, 13, 10183-10190 10.1039/c0cp02933e
22. Brede, J.; Linares, M.; Kuck, S.; Schwobel, J.; Scarfato, A.; Chang, S. H.; Hoffmann, G.; Wiesendanger, R.; Lensen, R.; Kouwer, P. H.; Hoogboom, J.; Rowan, A. E.; Broring, M.; Funk, M.; Stafstrom, S.; Zerbetto, F.; Lazzaroni, R. Dynamics of Molecular Self-ordering in Tetraphenyl Porphyrin Monolayers on Metallic Substrates Nanotechnology 2009, 20, 275602 10.1088/0957-4484/20/27/275602
23. Buchner, F.; Kellner, I.; Hieringer, W.; Görling, A.; Steinruck, H. P.; Marbach, H. Ordering Aspects and Intramolecular Conformation of Tetraphenylporphyrins on Ag(111) Phys. Chem. Chem. Phys. 2010, 12, 13082-13090 10.1039/c004551a
24. Rojas, G.; Chen, X.; Bravo, C.; Kim, J.-H.; Kim, J.-S.; Xiao, J.; Dowben, P. A.; Gao, Y.; Zeng, X. C.; Choe, W.; Enders, A. Self-Assembly and Properties of Nonmetalated Tetraphenyl-Porphyrin on Metal Substrates J. Phys. Chem. C 2010, 114, 9408-9415 10.1021/jp1012957
25. Diller, K.; Klappenberger, F.; Marschall, M.; Hermann, K.; Nefedov, A.; Wöll, C.; Barth, J. V. Self-metalation of 2H-tetraphenylporphyrin on Cu(111): an X-ray Spectroscopy Study J. Chem. Phys. 2012, 136, 014705 10.1063/1.3674165
26. 2(110) Surface Chem. Commun. 2014, 50, 8291-8294 10.1039/C4CC02919D
27. Wolfle, T.; Görling, A.; Hieringer, W. Conformational Flexibility of Metalloporphyrins Studied by Density-functional Calculations Phys. Chem. Chem. Phys. 2008, 10, 5739-5742 10.1039/b800566b
28. Tu, W.; Lei, J.; Wang, P.; Ju, H. Photoelectrochemistry of Free-base-Porphyrin-Functionalized Zinc Oxide Nanoparticles and their Applications in Biosensing Chem.-Eur. J. 2011, 17, 9440-9447 10.1002/chem.201100577
29. 2 Composite Films for VOC Optical Detection RSC Adv. 2014, 4, 1974-1981 10.1039/C3RA42443J
30. Zhang, Z.; Imae, T. Hydrogen-Bonding Stabilized Self-Assembled Monolayer Film of a functionalized Diacid, Protoporphyrin IX Zinc(II), onto a Gold Surface Nano Lett. 2001, 1, 241-243 10.1021/nl000192w
31. Xu, T.; Mohr, S.; Amende, M.; Laurin, M.; Döpper, T.; Görling, A.; Libuda, J. Benzoic Acid and Phthalic Acid on Atomically Well-Defined MgO(100) Thin Films: Adsorption, Interface Reaction, and Thin Film Growth J. Phys. Chem. C 2015, 119, 26968-26979 10.1021/acs.jpcc.5b07591
32. 3, and Supported Pd Model Catalysts from IR Spectroscopy J. Phys. Chem. C 2014, 118, 3188-3193 10.1021/jp5006692
33. Mohr, S.; Xu, T.; Döpper, T.; Laurin, M.; Görling, A.; Libuda, J. Molecular Orientation and Structural Transformations in Phthalic Anhydride Thin Films on MgO(100)/Ag(100) Langmuir 2015, 31, 7806-7814 10.1021/acs.langmuir.5b01392
34. 2 on Ordered Alumina Films and Mixed Baria-Alumina Nanoparticles: Cooperative Versus Non-cooperative Reaction Mechanisms J. Catal. 2008, 260, 315-328 10.1016/j.jcat.2008.09.020
35. University of Karlsruhe and Forschungszentrum Karlsruhe GmbH. TURBOMOLE, version 6.5, 2013; available from http://www.turbomole.com.
36. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-3868 10.1103/PhysRevLett.77.3865
37. Weigend, F.; Ahlrichs, R. Balanced Basis Sets of Split Valence, Triple Zeta Valence and Quadruple Zeta Valence Quality for H to Rn: Design and Assessment of Accuracy Phys. Chem. Chem. Phys. 2005, 7, 3297-3305 10.1039/b508541a
38. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. A Consistent and Accurate ab initio Parametrization of Density Functional Dispersion Correction (DFT-D) for the 94 Elements H-Pu J. Chem. Phys. 2010, 132, 154104 10.1063/1.3382344
39. Weigend, F. Accurate Coulomb-fitting Basis Sets for H to Rn Phys. Chem. Chem. Phys. 2006, 8, 1057-1065 10.1039/b515623h
40. Sierka, M.; Hogekamp, A.; Ahlrichs, R. Fast Evaluation of the Coulomb Potential for Electron Densities Using Multipole Accelerated Resolution of Identity Approximation J. Chem. Phys. 2003, 118, 9136-9148 10.1063/1.1567253