Skip to main content
SpringerLink
Log in

On-Surface (Cyclo-)Dehydrogenation Reactions: Role of Surface Diffusion

  • Conference paper
  • First Online:
On-Surface Synthesis

Part of the book series: Advances in Atom and Single Molecule Machines ((AASMM))

Abstract

Creating or connecting together large organic molecules, as polycyclic aromatic hydrocarbons (PAH), readily on surfaces arises as a step of paramount importance towards a true advance in the field of nanotechnology, and particularly of molecular electronics. On-surface synthesis can be regarded as an efficient means to build new molecular species by using bottom-up strategies. In particular, temperature-driven surface-catalysed cyclodehydrogenation (CDH) processes have burgeoned in last years as a novel and powerful route to efficiently transform (hetero-)aromatic molecular precursors into a large variety of a la carte hierarchical nanostructures: from fullerenes and triazafullerenes, aromatic domes, or nanotubes, to polymeric nanonetworks and, depending on the specific precursor utilized, even to pristine and functionalized graphene. In the first section of this chapter, the foundations and main aspects of the on-surface synthesis methodology and CDH reactions are revised, as well as the current status in the field up to the date. In Sect. 2, the most advanced first-principles theoretical tools currently available for the characterization of CDH processes will be summarized and described, including the novel theoretical strategies to monitorize CDH reaction paths and to calculate STM images. The following two sections will report on a very recently paradigmatic example related to the tailored formation of N-doped nanoarchitectures by diffusion-controlled on-surface (cyclo-)dehydrogenation of heteroaromatics, where the strength of the PAH–substrate interaction dramatically rules the competitive reaction pathways (CDH versus dehydrogenative polymerization). On the basis of those findings, the stepwise formation of N-doped nanohelicenes, nanographenes, nanodomes, molecular networks and graphene from the same heteroaromatic precursor through subsequent dehydrogenations on Pt(111) upon thermal-annealing will be fully described. The combined experimental (in situ UHV-STM, XPS and NEXAFS) and detailed computational DFT-based studies provide a full atomistic and chemical description of the intermediate reaction stages along the dehydrogenation path.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Champness, N.R.: Surface chemistry: Building with molecules. Nat. Nanotechnol. 2, 671 (2007)

    Article  CAS  Google Scholar 

  2. Martín-Gago, J.A.: Polycyclic aromatics: On-surface molecular engineering. Nat. Chem. 3, 11 (2011)

    Article  Google Scholar 

  3. Méndez, J., López, M.F., Martín-Gago, J.A.: On-surface synthesis of cyclic organic molecules. Chem. Soc. Rev. 40, 4578 (2011)

    Article  Google Scholar 

  4. Côté, A.P., Benin, A.I., Ockwig, N.W., O’Keeffe, M., Matzger, A.J., Yaghi, O.M.: Porous, crystalline, covalent organic frameworks. Science 310, 1166 (2005)

    Article  Google Scholar 

  5. Grill, L., Dyer, M., Lafferentz, L., Persson, M., Peters, M.V., Hecht, S.: Nano-architectures by covalent assembly of molecular building blocks. Nat. Nanotechnol. 2, 687 (2007)

    Article  CAS  Google Scholar 

  6. Weigelt, S., Busse, C., Bombis, C., Knudsen, M.M., Gothelf, K.V., Strunskus, T., Dahlbom, M., Besenbacher, F., Linderoth, T.R.: Covalent interlinking of an aldehyde and an amine on a Au(111) surface in ultrahigh vacuum. Angew. Chem. Int. Ed. 46, 9227 (2007)

    Article  CAS  Google Scholar 

  7. Rim, K.T., Siaj, M., Xiao, S., Myers, M., Carpentier, V.D., Liu, L., Su, C., Steigerwald, M.L., Hybertsen, M.S., McBreen, P.H., Flynn, G.W., Nuckolls, C.: Forming aromatic hemispheres on transition-metal surfaces. Angew. Chem. Int. Ed. 46, 7891 (2007)

    Article  CAS  Google Scholar 

  8. Otero, G., Biddau, G., Sánchez-Sánchez, C., Caillard, R., López, M.F., Rogero, C., Palomares, F.J., Cabello, N., Basanta, M.A., Ortega, J., Méndez, J., Echavarren, A.M., Pérez, R., Gómez-Lor, B., Martín-Gago, J.A.: Fullerenes from aromatic precursors by surface-catalysed cyclodehydrogenation. Nature 454, 865 (2008)

    Article  CAS  Google Scholar 

  9. Amsharov, K., Abdurakhmanova, N., Stepanow, S., Rauschenbach, S., Jansen, M., Kern, K.: Towards the isomer-specific synthesis of higher fullerenes and buckybowls by the surface-catalyzed cyclodehydrogenation of aromatic precursors. Angew. Chem. Int. Ed. 49, 9392 (2010)

    Article  CAS  Google Scholar 

  10. Treier, M., Pignedoli, C.A., Laino, T., Rieger, R., Müllen, K., Passerone, D., Fasel, R.: Surface-assisted cyclodehydrogenation provides a synthetic route towards easily processable and chemically tailored nanographenes. Nat. Chem. 3, 61 (2011)

    Article  CAS  Google Scholar 

  11. Cai, J., Ruffieux, P., Jaafar, R., Bieri, M., Braun, T., Blankenburg, S., Muoth, M., Seitsonen, A.P., Saleh, M., Feng, X., Müllen, K., Fasel, R.: Atomically precise bottom-up fabrication of graphene nanoribbons. Nature 466, 470 (2010)

    Article  CAS  Google Scholar 

  12. Pinardi, A.L., Otero-Irurueta, G., Palacio, I., Martínez, J.I., Sánchez-Sánchez, C., Tello, M., Rogero, C., Cossaro, A., Preobrajenski, A., Gómez-Lor, B., Jancarik, A., Stará, I.G., Stary, I., López, M.F., Méndez, J., Martín-Gago, J.A.: Tailored formation of N-doped nanoarchitectures by diffusion-controlled on-surface (cyclo)dehydrogenation of heteroaromatics. ACS Nano 7, 3676 (2013)

    Article  CAS  Google Scholar 

  13. Pinardi, A.L., Martínez, J.I., Jancarik, A., Stará, I.G., Stary, I., López, M.F., Méndez, J., Martín-Gago, J.A.: Sequential formation of N-doped nanohelicenes, nanographenes and nanodomes by surface-assisted chemical (cyclo)dehydrogenation of heteroaromatics. Chem. Commun. 50, 1555 (2014)

    Article  CAS  Google Scholar 

  14. Mueller, A., Amsharov, K.: Synthesis of precursors for large-diameter hemispherical buckybowls and precursors for short carbon nanotubes. Eur. J. Org. Chem. 36, 7153 (2012)

    Article  Google Scholar 

  15. Sánchez-Valencia, J.R., Dienel, T., Gröning, O., Shorubalko, I., Mueller, A., Jansen, M., Amsharov, K., Ruffieux, P., Fasel, R.: Controlled synthesis of single-chirality carbon nanotubes. Nature 512, 61 (2014)

    Article  Google Scholar 

  16. Bieri, M., Nguyen, M., Gro, O., Cai, J., Treier, M., Aït-Mansour, K., Ruffieux, P., Pignedoli, C.A., Passerone, D., Kastler, M., Mu, K.: Two-dimensional polymer formation on surfaces: insight into the roles of precursor mobility and reactivity. J. Amer. Chem. Soc. 132, 16669 (2010)

    Article  CAS  Google Scholar 

  17. Lipton-Duffin, J.A., Ivasenko, O., Perepichka, D.F., Rosei, F.: Synthesis of polyphenylene molecular wires by surface-confined polymerization. Small 5, 592 (2009)

    Article  CAS  Google Scholar 

  18. Lafferentz, L., Ample, F., Yu, H., Hecht, S., Joachim, C., Grill, L.: Conductance of a single conjugated polymer as a continuous function of its length. Science 323, 1193 (2009)

    Article  CAS  Google Scholar 

  19. Dinca, L.E., Fu, C., MacLeod, J.M., Lipton-Duffin, J., Brusso, J.L., Szakacs, C.E., Ma, D., Perepichka, D.F., Rosei, F.: Unprecedented transformation of tetrathienoanthracene into pentacene on Ni(111). ACS Nano 7, 1652 (2013)

    Article  CAS  Google Scholar 

  20. Lafferentz, L., Eberhardt, V., Dri, C., Africh, C., Comelli, G., Esch, F., Hecht, S., Grill, L.: Controlling on-surface polymerization by hierarchical and substrate-directed growth. Nat. Chem. 4, 215 (2012)

    Article  CAS  Google Scholar 

  21. Kittelmann, M., Rahe, P., Nimmrich, M., Hauke, C.M., Ku, A.: On-Surface Covalent Linking of Organic Building Blocks on a Bulk Insulator. ACS Nano 5, 8420 (2011)

    Article  CAS  Google Scholar 

  22. Sánchez-Sánchez, C., Martínez, J.I., Lanzilotto, V., Biddau, G., Gómez-Lor, B., Pérez, R., Floreano, L., López, M.F., Martín-Gago, J.A.: Chemistry and temperature-assisted dehydrogenation of C60H30 molecules on TiO2(110) surfaces. Nanoscale 5, 11058 (2013)

    Article  Google Scholar 

  23. Bartels, L.: Tailoring molecular layers at metal surfaces. Nat. Chem. 2, 87 (2010)

    Article  CAS  Google Scholar 

  24. Gourdon, A.: On-surface covalent coupling in ultrahigh vacuum. Angew. Chem. Int. Ed. 47, 6950 (2008)

    Article  CAS  Google Scholar 

  25. Lackinger, M., Heckl, W.M.: Perspective on covalent intermolecular coupling reactions on surfaces. J. Phys. D Appl. Phys. 44, 1 (2011)

    Article  Google Scholar 

  26. Palma, C.A., Samori, P.: Homo-coupling of terminal alkynes on a noble metal surface. Nat. Chem. 3, 431 (2011)

    Article  CAS  Google Scholar 

  27. Zhong, D., Franke, J.H., Podiyanachari, S.K., Blömker, T., Zhang, H., Kehr, G., Erker, G., Fuchs, H., Chi, L.: Linear alkane polymerization on a gold surface. Science 334, 213 (2011)

    Article  CAS  Google Scholar 

  28. Usachov, D., Vilkov, O., Grüneis, A., Haberer, D., Fedorov, A., Adamchuk, V.K., Preobrajenski, A.B., Dudin, P., Barinov, A., Oehzelt, M., Laubschat, C., Vyalikh, D.V.: Nitrogen-doped graphene: efficient growth, structure, and electronic properties. Nanoletters 11, 5401 (2011)

    Article  CAS  Google Scholar 

  29. Barth, J.V., Costantini, G., Kern, K.: Engineering atomic and molecular nanostructures at surfaces. Nature 437, 671 (2005)

    Article  CAS  Google Scholar 

  30. Fuhrmann, T., Kinne, M., Tränkenschuh, B., Papp, C., Zhu, J.F., Denecke, R., Steinrück, H.P.: Activated adsorption of methane on Pt(1 1 1) — an in situ XPS study. New J. Phys. 7, 107 (2005)

    Article  Google Scholar 

  31. Ugeda, M., Fernández-Torre, D., Brihuega, I., Pou, P., Martínez-Galera, A., Pérez, R., Gómez-Rodríguez, J.: Point defects on graphene on metals. Phys. Rev. Lett. 107, 116803 (2011)

    Article  CAS  Google Scholar 

  32. Manner, W.L., Girolami, G.S., Nuzzo, R.G.: Sequential dehydrogenation of unsaturated cyclic C5 and C6 hydrocarbons on Pt(111). J. Phys. Chem. B 102, 10295 (1998)

    Article  CAS  Google Scholar 

  33. Streitwieser, A., Heathcock, C.H.: Introduction to Organic Chemistry. Macmillan, New York (1985)

    Google Scholar 

  34. Gómez-Lor, B., Echavarren, A.M.: Synthesis of a triaza analogue of crushed-fullerene by intramolecular palladium-catalyzed arylation. Org. Lett. 6, 2993 (2004)

    Article  Google Scholar 

  35. Otero, G., Biddau, G., Ozaki, T., Gómez-Lor, B., Méndez, J., Pérez, R., Martín-Gago, J.A.: Spontaneous discrimination of polycyclic aromatic hydrocarbon (PAH) enantiomers on a metal surface. Chemistry. A Eur. J. 16, 13920 (2010)

    Article  CAS  Google Scholar 

  36. Lewis, J.P., Jelínek, P., Ortega, J., Demkov, A.A., Trabada, D.G., Haycock, B., Wang, H., Adams, G., Tomfohr, J.K., Abad, E., Wang, H., Drabold, D.A.: Advances and applications in the FIREBALL ab initio tight-binding molecular-dynamics formalism. Phys. Stat. Sol. B 248, 1989 (2011)

    CAS  Google Scholar 

  37. GAUSSIAN, Gaussian, Inc., Wallingford. URL: www.gaussian.com (2009)

  38. Soler, J.M., Artacho, E., Gale, J.D., García, A., Junquera, J., Ordejón, P., Sánchez-Portal, D.: The SIESTA method for ab initio order-N materials simulation. J. Phys. Cond. Matt. 14, 2745 (2002)

    Article  CAS  Google Scholar 

  39. Giannozzi, P., et al.: QUANTUM ESPRESSO: a modular and open-source software project for quantum simulations of materials. J. Phys.: Condens. Matter 21, 395502 (2009)

    Google Scholar 

  40. Hafner, J.: Ab-initio simulations of materials using VASP: density-functional theory and beyond. J. Comput. Chem. 29, 2044 (2008)

    Article  CAS  Google Scholar 

  41. Gonze, X., et al.: ABINIT: First-principles approach to material and nanosystem properties. Comput. Phys. Commun. 180, 2582 (2009)

    Article  CAS  Google Scholar 

  42. Abad, E., Dappe, Y.J., Martínez, J.I., Flores, F., Ortega, J.: C6H6/Au(111): Interface dipoles, band alignment, charging energy, and van der Waals interaction. J. Chem. Phys. 134, 044701 (2011)

    Article  CAS  Google Scholar 

  43. Dappe, Y.J., Basanta, M.A., Ortega, J., Flores, F.: Weak chemical interaction and van der Waals forces between graphene layers: a combined density functional and intermolecular perturbation theory approach. Phys. Rev. B 74, 205434 (2006)

    Article  Google Scholar 

  44. Basanta, M.A., Dappe, Y.J., Ortega, J., Flores, F.: Van der Waals forces in the local-orbital density functional theory. Europhys. Lett. 70, 355 (2005)

    Article  CAS  Google Scholar 

  45. Barone, V., Casarin, M., Forrer, D., Pavone, M., Sambi, M., Vittadini, A.: Role and effective treatment of dispersive forces in materials: polyethylene and graphite crystals as test cases. J. Comput. Chem. 30, 934 (2009)

    Article  CAS  Google Scholar 

  46. Elstner, M., Hobza, P., Frauenheim, T., Suhai, S., Kaxiras, E.: Hydrogen bonding and stacking interactions of nucleic acid base pairs: a density-functional-theory based treatment. J. Chem. Phys. 114, 5149 (2001)

    Article  CAS  Google Scholar 

  47. Gavezzotti, A.: The calculation of molecular volumes and the use of volume analysis in the investigation of structured media and of solid-state organic reactivity. J. Am. Chem. Soc. 105, 5220 (1983)

    Article  CAS  Google Scholar 

  48. Dunitz, J.D., Gavezzotti, A.: Attractions and repulsions in organic crystals: what can be learned from the crystal structures of condensed-ring aromatic hydrocarbons? Acc. Chem. Res. 32, 677 (1999)

    Article  CAS  Google Scholar 

  49. Filippini, G., Gavezzotti, A.: Empirical intermolecular potentials for organic crystals: the 6-exp’ approximation revisited. Acta Crystallogr. Sect. B: Struct. Sci. 49, 868 (1993)

    Article  Google Scholar 

  50. Mowbray, D.J., Martínez, J.I., García-Lastra, J.M., Thygesen, K.S., Jacobsen, K.W.J.: Stability and electronic properties of TiO2 nanostructures with and without B and N doping. J. Phys. Chem. C 113, 12301 (2009)

    Article  CAS  Google Scholar 

  51. Martínez, J.I., García-Lastra, J.M., López, M.J., Alonso, J.A.: Optical to ultraviolet spectra of sandwiches of benzene and transition metal atoms: time dependent density functional theory and many-body calculations. J. Chem. Phys. 132, 044314 (2010)

    Article  Google Scholar 

  52. Martínez, J.I., Abad, E., Flores, F., Ortega, J.: Simulating the organic-molecule/metal interface TCNQ/Au(111). Phys. Stat. Sol. B 248, 2044 (2011)

    Article  Google Scholar 

  53. Martínez, J.I., Abad, E., Flores, F., Ortega, J., Brocks, G.: Barrier height formation in organic blends/metal interfaces: case of tetrathiafulvalene-tetracyanoquinodimethane/Au. Chem. Phys. 390, 14 (2011)

    Article  Google Scholar 

  54. Hybertsen, M.S., Louie, S.G.: First-principles theory of quasiparticles: calculation of band gaps in semiconductors and insulators. Phys. Rev. Lett. 55, 1418 (1985)

    Article  CAS  Google Scholar 

  55. Hybertsen, M.S., Louie, S.G.: Electron correlation in semiconductors and insulators: band gaps and quasiparticle energies. Phys. Rev. B 34, 5390 (1986)

    Article  CAS  Google Scholar 

  56. Marini, A., Hogan, C., Grüning, M., Varsano, D.: YAMBO: An ab initio tool for excited state calculations. Comput. Phys. Commun. 180, 1392 (2009)

    Article  CAS  Google Scholar 

  57. Rohlfing, M., Louie, S.G.: Excitons and optical spectrum of the Si(111)−(2×1) surface. Phys. Rev. Lett. 83, 856 (1999)

    Article  CAS  Google Scholar 

  58. Onida, G., Reining, L., Rubio, A.: Electronic excitations: density-functional versus many-body Green’s-function approaches. Rev. Mod. Phys. 74, 601 (2002)

    Article  CAS  Google Scholar 

  59. Berne, B.J., Cicotti, G., Coker, D.F.: Classical and Quantum Dynamics in Condensed Phase Simulations. World Scientific Publishing Company, Singapore (1998)

    Book  Google Scholar 

  60. Henkelman, G., Jonsson, H.J.: Improved tangent estimate in the nudged elastic band method for finding minimum energy paths and saddle points. Chem. Phys. 113, 9978 (2000)

    CAS  Google Scholar 

  61. Henkelman, G., Uberuaga, B.P., Jonsson, H.J.: A climbing image nudged elastic band method for finding saddle points and minimum energy paths. Chem. Phys. 113, 9901 (2000)

    CAS  Google Scholar 

  62. Blanco, J.M., González, C., Jelínek, P., Ortega, J., Flores, F., Pérez, R.: First-principles simulations of STM images: from tunneling to the contact regime. Phys. Rev. B 70, 085405 (2004)

    Article  Google Scholar 

  63. Blanco, J.M., Flores, F., Pérez, R.: STM-theory: image potential, chemistry and surface relaxation. Prog. Surf. Sci. 81, 403 (2006)

    Article  CAS  Google Scholar 

  64. Martínez, J.I., Abad, E., González, C., Flores, F., Ortega, J.: Improvement of scanning tunneling microscopy resolution with H-sensitized tips. Phys. Rev. Lett. 108, 246102 (2012)

    Article  Google Scholar 

  65. Sánchez-Sánchez, C., González, C., Jelínek, P., Méndez, J., de Andres, P.L., Martín-Gago, J.A., López, M.F.: Understanding atomic-resolved STM images on TiO2(110)-(1×1) surface by DFT calculations. Nanotechnology 21, 405702 (2010)

    Article  Google Scholar 

  66. Martínez, J.I., Abad, E., González, C., Ortega, J., Flores, F.: Theoretical characterization of the TTF/Au(111) interface: STM imaging, band alignment and charging energy. Org. Electron. 13, 399 (2012)

    Article  Google Scholar 

  67. Tersoff, J., Hamann, D.R.: Theory and application for the scanning tunneling microscope. Phys. Rev. Lett. 50, 1998 (1983)

    Article  CAS  Google Scholar 

  68. Tersoff, J., Hamann, D.R.: Theory of the scanning tunneling microscope. Phys. Rev. B 31, 805 (1985)

    Article  CAS  Google Scholar 

  69. Gross, L., Moll, N., Mohn, F., Curioni, A., Meyer, G., Hanke, F., Persson, M.: High-resolution molecular orbital imaging using a p-wave STM tip. Phys. Rev. Lett. 107, 086101 (2011)

    Article  Google Scholar 

  70. Pinardi, A.L., Biddau, G., van de Ruit, K., Otero-Irurueta, G., Gardonio, S., Lizzit, S., Schennach, R., Flipse, C.F.J., López, M.F., Méndez, J., Pérez, R., Martín-Gago, J.A.: Vacancy formation on C60/Pt (111): unraveling the complex atomistic mechanism. Nanotech. 25, 385602 (2014)

    Article  Google Scholar 

  71. Weiss, K., Beernink, G., Dötz, F., Birkner, A., Müllen, K., Wöll, C.: Template-mediated synthesis of polycyclic aromatic hydrocarbons: cyclodehydrogenation and planarization of a hexaphenylbenzene derivative at a copper surface. Angew. Chem. Int. Ed. 38, 3748 (1999)

    Article  CAS  Google Scholar 

  72. Beernink, G., Gunia, M., Dötz, F., Öström, H., Weiss, K., Müllen, K., Wöll, C.: Synthesis of polycyclic aromatic hydrocarbons and graphite islands via surface-induced reaction of small molecules. ChemPhysChem 2, 317 (2001)

    Article  CAS  Google Scholar 

  73. Martínez-Galera, A.J., Brihuega, I., Gómez-Rodríguez, J.M.: Ethylene irradiation: a new route to grow graphene on low reactivity metals. Nanolett. 11, 3576 (2011)

    Article  Google Scholar 

  74. Zhao, L., He, R., Rim, K.T., Schiros, T., Kim, K.S., Zhou, H., Gutierrez, C., Chockalingam, S.P., Arguello, C.J., Palova, L., Nordlund, D., Hybertsen, M.S., Reichman, D.R., Heinz, T.F., Kim, P., Pinczuk, A., Flynn, G.W., Pasupathy, A.N.: Visualizing individual nitrogen dopants in monolayer graphene. Science 333, 999 (2011)

    Article  CAS  Google Scholar 

  75. Violi, A.: Cyclodehydrogenation reactions to cyclopentafused polycyclic aromatic hydrocarbons. J. Phys. Chem. A 109, 7781 (2005)

    Article  CAS  Google Scholar 

  76. Lizzit, S., Baraldi, A.: High-resolution fast X-ray photoelectron spectroscopy study of ethylene interaction with Ir(111): from chemisorption to dissociation and graphene formation. Catal. Today 154, 68 (2010)

    Article  CAS  Google Scholar 

  77. Oji, H., Mitsumoto, R., Ito, E., Ishii, H., Ouchi, Y., Seki, K., Yokoyama, T., Ohta, T., Kosugi, N.: Core hole effect in NEXAFS spectroscopy of polycyclic aromatic hydrocarbons: benzene, chrysene, perylene, and coronene. J. Chem. Phys. 109, 10409 (1998)

    Article  CAS  Google Scholar 

  78. Zhang, W., Nefedov, A., Naboka, M., Cao, L., Wöll, C.: Molecular orientation of terephthalic acid assembly on epitaxial graphene: NEXAFS and XPS study. PhysChemChemPhys 14, 10125 (2012)

    CAS  Google Scholar 

  79. Weiss, K., Gebert, S., Wühn, M., Wadepohl, H., Wöll, C.: Near edge x-ray absorption fine structure study of benzene adsorbed on metal surfaces: comparison to benzene cluster complexes. J. Vac. Sci. Tech. A 16, 1017 (1998)

    Article  CAS  Google Scholar 

  80. Lee, V., Park, C., Jaye, C., Fischer, D.A., Yu, Q., Wu, W., Liu, Z., Bao, J., Pei, S.S., Smith, C., Lysaght, P., Banerjee, S.: Substrate hybridization and rippling of graphene evidenced by near-edge X-ray absorption fine structure spectroscopy. J. Phys. Chem. Lett. 1, 1247 (2010)

    Article  CAS  Google Scholar 

  81. Schultz, B.J., Patridge, C.J., Lee, V., Jaye, C., Lysaght, P.S., Smith, C., Barnett, J., Fischer, D.A., Prendergast, D., Banerjee, S.: Imaging local electronic corrugations and doped regions in graphene. Nat. Commun. 2, 372 (2011)

    Article  Google Scholar 

  82. Schmidt, N., Fink, R., Hieringer, W.: Assignment of near-edge x-ray absorption fine structure spectra of metalloporphyrins by means of time-dependent density-functional calculations. J. Chem. Phys. 133, 054703 (2010)

    Article  Google Scholar 

  83. Kikuma, J., Yoneyama, K., Nomura, M., Konishi, T., Hashimoto, T., Mitsumoto, R., Ohuchi, Y., Seki, K.: Surface analysis of CVD carbon using NEXAFS, XPS and TEM. J. Elec. Spec. Rel. Phen. 88, 919 (1998)

    Article  Google Scholar 

  84. Preobrajenski, A.B., Ng, M.L., Vinogradov, A.S., Mårtensson, N.: Controlling graphene corrugation on lattice-mismatched substrates. Phys. Rev. B 78, 073401 (2008)

    Article  Google Scholar 

  85. Dedkov, Y.S., Sicot, M., Fonin, M.: X-ray absorption and magnetic circular dichroism of graphene/Ni(111). J. Appl. Phys. 107, 09E121 (2010)

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department Surfaces, Coatings and Molecular Astrophysics, Institute of Materials Science of Madrid (ICMM-CSIC), 28049, Madrid, Spain

    José A. Martín-Gago, Anna L. Pinardi & José I. Martínez

Authors
  1. José A. Martín-Gago
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Anna L. Pinardi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. José I. Martínez
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to José A. Martín-Gago .

Editor information

Editors and Affiliations

  1. CEMES-CNRS, Toulouse, France

    André Gourdon

Rights and permissions

Reprints and permissions

Copyright information

© 2016 Springer International Publishing Switzerland

About this paper

Cite this paper

Martín-Gago, J.A., Pinardi, A.L., Martínez, J.I. (2016). On-Surface (Cyclo-)Dehydrogenation Reactions: Role of Surface Diffusion. In: Gourdon, A. (eds) On-Surface Synthesis. Advances in Atom and Single Molecule Machines. Springer, Cham. https://doi.org/10.1007/978-3-319-26600-8_3

Download citation

Publish with us

Policies and ethics

Search

Navigation