Asymmetric response toward molecular fluorination in binary copper-phthalocyanine/pentacene assemblies

Journal of Physical Chemistry C

Volumn 118, Issue 32, 2014, Pages 18626-18630

  De Oteyza, D G ^a,b   Garcia Lastra, J M ^c   Goiri, E ^a   El Sayed, A ^b   Wakayama, Y ^d   Ortega, J E ^a,b  

^a DONOSTIA INTERNATIONAL PHYSICS CENTER DIPC   (Spain)

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

^c TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^d NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINATION; FLUORINE; GOLD; HALOGENATION; HYDROGEN BONDS; MOLECULES;

ASYMMETRIC RESPONSE; COPPER PHTHALOCYANINE; CRYSTALLINE STRUCTURE; INTERACTION POTENTIALS; INTERMOLECULAR HYDROGEN BONDS; INTERMOLECULAR INTERACTIONS; MOLECULAR SELF ASSEMBLY; PENTACENES;

SUBSTRATES;

EID: 84906256528     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp506151j     Document Type: Article

References (22)

1. Elemans, J. A. A. W.; Lei, S.; De Feyter, S. Molecular and Supramolecular Networks on Surfaces: From Two-Dimensional Crystal Engineering to Reactivity Angew. Chem., Int. Ed. 2009, 48, 7298-7332
2. Bartels, L. Tailoring Molecular Layers at Metal Surfaces Nat. Chem. 2010, 2, 87-95
3. El-Sayed, A.; Borghetti, P.; Goiri, E.; Rogero, C.; Floreano, L.; Lovat, G.; Mowbray, D. J.; Cabellos, J. L.; Wakayama, Y.; Rubio, A. Understanding Energy-Level Alignment in DonorAcceptor/Metal Interfaces from Core-Level Shifts ACS Nano 2013, 7, 6914-6920
4. Hipps, K. W.; Scudiero, L.; Barlow, D. E.; Cooke, M. P. A Self-Organized 2-Dimensional Bifunctional Structure Formed by Supramolecular Design J. Am. Chem. Soc. 2002, 124, 2126-2127
5. Chen, W.; Li, H.; Huang, H.; Fu, Y.; Zhang, H. L.; Ma, J.; Wee, A. T. S. Two-Dimensional Pentacene:3,4,9,10-Perylenetetracarboxylic Dianhydride Supramolecular Chiral Networks on Ag(111) J. Am. Chem. Soc. 2008, 130, 12285-12289
6. Theobald, J. A.; Oxtoby, N. S.; Phillips, M. A.; Champness, N. R.; Beton, P. H. Controlling Molecular Deposition and Layer Structure with Supramolecular Surface Assemblies Nature 2003, 424, 1029
7. Perdigao, L. M. A.; Champness, N. R.; Beton, P. H. Surface Self-Assembly of the Cyanuric Acid-Melamine Hydrogen Bonded Network Chem. Commun. 2006, 538-540
8. Cañas-Ventura, M. E.; Xiao, W.; Wasserfallen, D.; Müllen, K.; Brune, H.; Barth, J. V.; Fasel, R. Self-Assembly of Periodic Bicomponent Wires and Ribbons Angew. Chem., Int. Ed. 2007, 46, 1814-1818
9. Ruiz-Oses, M.; Gonzalez-Lakunza, N.; Silanes, I.; Gourdon, A.; Arnau, A.; Ortega, J. E. Self-Assembly of Heterogeneous Supramolecular Structures with Uniaxial Anisotropy J. Phys. Chem. B 2006, 110, 25573-25577
10. Barrena, E.; de Oteyza, D. G.; Dosch, H.; Wakayama, Y. 2D Supramolecular Self-Assembly of Binary Organic Monolayers ChemPhysChem 2007, 8, 1915-1918
11. Huang, Y. L.; Chen, W.; Li, H.; Ma, J.; Pflaum, J.; Wee, A. T. S. Tunable Two-Dimensional Binary Molecular Networks Small 2010, 6, 70-75
12. 16CuPc and Pentacene ACS Nano 2011, 5, 581-589
13. Tang, M. L.; Bao, Z. Halogenated Materials as Organic Semiconductors Chem. Mater. 2011, 23, 446-455
14. Lo, Y.-Y.; Chang, J.-H.; Hoffmann, G.; Su, W.-B.; Wu, C.; Chang, C.-S. A Comparative Study on the Adsorption Behavior of Pentacene and Perfluoropentacene Molecules on Au(111) Surfaces Jpn. J. Appl. Phys. 2013, 52, 101601-1-6
15. Allen, F. H.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. Typical Interatomic Distances: Organic Compounds Int. Tables Crystallogr. 2006, C, 790-811
16. Steiner, T. The Hydrogen Bond in the Solid State Angew. Chem., Int. Ed. 2002, 41, 48-76
17. El-Sayed, A.; Mowbray, D. J.; Garcia-Lastra, J. M.; Rogero, C.; Goiri, E.; Borghetti, P.; Turak, A.; Doyle, B. P.; Dell'Angela, M.; Floreano, L. Supramolecular Environment-Dependent Electronic Properties of Metal-Organic Interfaces J. Phys. Chem. C 2012, 116, 4780-4785
18. Goiri, E.; Matena, M.; El-Sayed, A.; Lobo-Checa, J.; Borghetti, P.; Rogero, C.; Detlefs, B.; Duvernay, J.; Ortega, J. E.; Oteyza, D. G. Self-Assembly of Bicomponent Molecular Monolayers: Adsorption Height Changes and Their Consequences Phys. Rev. Lett. 2014, 112, 117602-1-5
19. Hammer, B.; Norskov, J. K. Why Gold is the Noblest of All Metals Nature 1995, 376, 238-240
20. Horcas, I.; Fernandez, R.; Gomez-Rodriguez, J. M.; Colchero, J.; Gomez-Herrero, J.; Baro, A. M. WSxM: A Software for Scanning Probe Microscopy and a Tool for Nanotechnology Rev. Sci. Instrum. 2007, 78, 013705-1-8
21. Perdew, J. P.; Zunger, A. Self-Interaction Correction to Density-Functional Approximations for Many-Electron Systems Phys. Rev. B 1981, 23, 5048-5079
22. Goiri, E.; García-Lastra, J. M.; Corso, M.; Adb El-Fattah, Z. M.; Ortega, J. E.; de Oteyza, D. G. Understanding Periodic Dislocations in 2D Supramolecular Crystals: The PFP/Ag(111) Interface J. Phys. Chem. Lett. 2012, 3, 848-852