Tailored formation of n-doped nanoarchitectures by diffusion-controlled on-surface (Cyclo)Dehydrogenation of heteroaromatics

ACS Nano

Volumn 7, Issue 4, 2013, Pages 3676-3684

  Pinardi, Anna Lisa ^a   Otero Irurueta, Gonzalo ^a   Palacio, Irene ^a   Martinez, Jose Ignacio ^a   Sanchez Sanchez, Carlos ^a   Tello, Marta ^a   Rogero, Celia ^b   Cossaro, Albano ^c   Preobrajenski, Alexei ^d   Gómez Lor, Berta ^a   Jancarik, Andrej ^e   Stará, Irena G ^e   Starý, Ivo ^e   Lopez, M Francisca ^a   Méndez, Javier ^a   Martin Gago, Jose Angel ^a,f  

^a INSTITUTO DE CIENCIA DE MATERIALES DE MADRID   (Spain)

^b CENTRO MIXTO CSIC UPV EHU   (Spain)

^c LABORATORIO TASC   (Italy)

^d LUND UNIVERSITY   (Sweden)

^e INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^f CENTRO DE ASTROBIOLOGÍA CSIC INTA   (Spain)

Author keywords

bottom up assembling; heteroaromatic polymer; N doped nanographene; STM; surface diffusion; surface assisted dehydrogenation

Indexed keywords

BOTTOM-UP ASSEMBLING; COMPETITIVE REACTIONS; CYCLODEHYDROGENATION; DEHYDROGENATIVE POLYMERIZATION; HETEROAROMATIC POLYMERS; MOLECULAR BUILDING BLOCKS; N-DOPED; STM;

DOPING (ADDITIVES); GRAPHENE; MACHINERY; MONOLAYERS; OLIGOMERS; POLYCYCLIC AROMATIC HYDROCARBONS; POLYMERIZATION; POLYMERS; SURFACE DIFFUSION; TWO DIMENSIONAL;

DEHYDROGENATION;

HYDROGEN; NANOMATERIAL; POLYCYCLIC AROMATIC HYDROCARBON; MACROMOLECULE;

ARTICLE; CHEMISTRY; CONFORMATION; CRYSTALLIZATION; DIFFUSION; ISOLATION AND PURIFICATION; MACROMOLECULE; MATERIALS TESTING; METHODOLOGY; PARTICLE SIZE; SURFACE PROPERTY; ULTRASTRUCTURE; PROCEDURES;

CRYSTALLIZATION; DIFFUSION; HYDROGEN; MACROMOLECULAR SUBSTANCES; MATERIALS TESTING; MOLECULAR CONFORMATION; NANOSTRUCTURES; PARTICLE SIZE; POLYCYCLIC HYDROCARBONS, AROMATIC; SURFACE PROPERTIES;

EID: 84876554332     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn400690e     Document Type: Article

References (42)

1. Wei, D.; Liu, Y. Controllable Synthesis of Graphene and Its Applications Adv. Mater. 2010, 22, 3225-3241
2. Méndez, J.; López, M. F.; Martín-Gago, J. A. On-Surface Synthesis of Cyclic Organic Molecules Chem. Soc. Rev. 2011, 40, 4578-4590
3. Otero, G.; Biddau, G.; Sánchez-Sánchez, C.; Caillard, R.; López, M. F.; Rogero, C.; Palomares, F. J.; Cabello, N.; Basanta, M. A.; Ortega, J. et al. Fullerenes from Aromatic Precursors by Surface-Catalysed Cyclodehydrogenation Nature 2008, 454, 865-869
4. 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. 2010, 49, 1-6
5. 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. 2011, 3, 61-67
6. Cai, J.; Ruffieux, P.; Jaafar, R.; Bieri, M.; Braun, T.; Blankenburg, S.; Muoth, M.; Seitsonen, A. P.; Saleh, M.; Feng, X. et al. Atomically Precise Bottom-up Fabrication of Graphene Nanoribbons Nature 2010, 466, 470-473
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. et al. Forming Aromatic Hemispheres on Transition-Metal Surfaces Angew. Chem., Int. Ed. 2007, 46, 7891-7895
8. Grill, L.; Dyer, M.; Lafferentz, L.; Persson, M.; Peters, M. V; Hecht, S. Nano-Achitectures by Covalent Assembly of Molecular Building Blocks Nat. Nanotechnol. 2007, 2, 687-691
9. 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. 2012, 4, 215-220
10. Lipton-Duffin, J. A.; Ivasenko, O.; Perepichka, D. F.; Rosei, F. Synthesis of Polyphenylene Molecular Wires by Surface-Confined Polymerization Small 2009, 5, 592-759
11. 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 2009, 323, 1193-1198
12. Bieri, M.; Nguyen, M.; Gro, O.; Cai, J.; Treier, M.; At-Mansour, K.; Ruffieux, P.; Pignedoli, C. A.; Passerone, D.; Kastler, M. et al. Two-Dimensional Polymer Formation on Surfaces: Insight into the Roles of Precursor Mobility and Reactivity J. Am. Chem. Soc. 2010, 132, 16669-16676
13. 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 2011, 5, 8420-8425
14. Usachov, D.; Vilkov, O.; Grüneis, A.; Haberer, D.; Fedorov, A.; Adamchuk, V. K.; Preobrajenski, A. B.; Dudin, P.; Barinov, A.; Oehzelt, M. et al. Nitrogen-Doped Graphene: Efficient Growth, Structure, and Electronic Properties Nano Lett. 2011, 11, 5401-5407
15. Gourdon, A. On-Surface Covalent Coupling in Ultrahigh Vacuum Angew. Chem., Int. Ed. 2008, 47, 6950-6953
16. Bartels, L. Tailoring Molecular Layers at Metal Surfaces Nat. Chem. 2010, 2, 87-95
17. Franc, G.; Gourdon, A. Covalent Networks through On-Surface Chemistry in Ultra-High Vacuum: State-of-the-Art and Recent Developments Phys. Chem. Chem. Phys. 2011, 13, 14283-14292
18. Lackinger, M.; Heckl, W. M. A STM Perspective on Covalent Intermolecular Coupling Reactions on Surfaces J. Phys. D: Appl. Phys. 2011, 44, 1-14
19. Palma, C. A.; Samorì, P. Blueprinting Macromolecular Electronics Nat. Chem. 2011, 3, 431-436
20. In't Veld, M.; Iavicoli, P.; Haq, S.; Amabilino, D. B.; Raval, R. Unique Intermolecular Reaction of Simple Porphyrins at a Metal Surface Gives Covalent Nanostructures Chem. Commun. 2008, 1536-1538
21. 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 2011, 334, 213-216
22. Matena, M.; Riehm, T.; Stöhr, M.; Jung, T. A.; Gade, L. H. Transforming Surface Coordination Polymers into Covalent Surface Polymers: Linked Polycondensed Aromatics through Oligomerization of N-Heterocyclic Carbene Intermediates Angew. Chem., Int. Ed. 2008, 47, 2414-2417
23. Kanuru, V. K.; Kyriakou, G.; Beaumont, S. K.; Papageorgiou, A. C.; Watson, D. J.; Lambert, R. M. Sonogashira Coupling on an Extended Gold Surface in Vacuo: Reaction of Phenylacetylene with Iodobenzene on Au(111) J. Am. Chem. Soc. 2010, 132, 8081-8086
24. Lipton-Duffin, J. A.; Miwa, J. A.; Kondratenko, M.; Cicoira, F.; Sumpter, B. G.; Meunier, V.; Perepichka, D. F.; Rosei, F. Step-by-Step Growth of Epitaxially Aligned Polythiophene by Surface-Confined Reaction P. Natl. Acad. Sci. U.S.A. 2010, 107, 11200-11204
25. Gutzler, R.; Walch, H.; Eder, G.; Kloft, S.; Heckl, W. M.; Lackinger, M. Surface Mediated Synthesis of 2D Covalent Organic Frameworks: 1,3,5-Tris(4-bromophenyl)benzene on Graphite(001), Cu(111), and Ag(110) Chem. Commun. 2009, 4456-4458
26. Gómez-Lor, B.; Echavarren, A. M. Synthesis of a Triaza Analogue of Crushed-Fullerene by Intramolecular Palladium-Catalyzed Arylation Org. Lett. 2004, 6, 2993-2996
27. Jančařík, A.; Stará, I. G.; Starý, I. To be published.
28. Violi, A. Cyclodehydrogenation Reactions to Cyclopentafused Polycyclic Aromatic Hydrocarbons J. Phys. Chem. A 2005, 109, 7781-7787
29. 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 Chem.-Eur. J. 2010, 16, 13920-13924
30. Liu, C.; Qin, Z.; Chen, J.; Guo, Q.; Yu, Y.; Cao, G. Molecular Orientations and Interfacial Structure of C60 on Pt(111) J. Chem. Phys. 2011, 134, 164707
31. 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. 1999, 38, 3748-3752
32. 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 2001, 2, 317-320
33. Henkelman, G.; Uberuaga, B. P.; Jónsson, H. A Climbing Image Nudged Elastic Band Method for Finding Saddle Points and Minimum Energy Paths J. Chem. Phys. 2000, 113, 9901-9904
34. Martínez-Galera, A. J.; Brihuega, I.; Gómez- Rodríguez, J. M. Ethylene Irradiation: A New Route to Grow Graphene on Low Reactivity Metals Nano Lett. 2011, 11, 3576-3580
35. Wang, H.; Maiyalagan, T.; Wang, X. Review on Recent Progress in Nitrogen-Doped Graphene: Synthesis, Characterization, and Its Potential Applications ACS Catal. 2012, 2, 781-794
36. Preobrajenski, A. B.; Ng, M. L.; Vinogradov, A. S.; MaÌŠ rtensson, N. Controlling Graphene Corrugation on Lattice-Mismatched Substrates Phys. Rev. B 2008, 78, 2-5
37. Horcas, I.; Fernández, R.; Gómez-Rodríguez, J. M.; Colchero, J.; Gómez-Herrero, J.; Baro, a M. WSXM: A Software for Scanning Probe Microscopy and a Tool for Nanotechnology Rev. Sci. Instrum. 2007, 78, 013705
38. Lewis, J. P.; Jelínek, P.; Ortega, J.; Demkov, A. A.; Trabada, D. G.; Haycock, B.; Wang, H.; Adams, G.; Tomfohr, J. K.; Abad, E. et al. Advances and Applications in the FIREBALL ab Initio Tight-Binding Molecular-Dynamics Formalism Phys. Status Solidi B 2011, 248, 1989-2007
39. Baroni, S.; Corso, A. D.; De Gironcoli, S.; Giannozzi, P. QUANTUMESPRESSO package, www.quantum-espresso.org.
40. 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. 2011, 134, 044701
41. Perdew, J. P.; Jackson, K. A.; Pederson, M. R.; Singh, D. J.; Fiolhais, C. Atoms, Molecules, Solids and Surfaces: Applications of the Generalized Gradient Approximation for Exchange and Correlation Phys. Rev. B 1992, 46, 6671-6687
42. Vanderbilt, D. Soft Self-Consistent Pseudopotentials in a Generalized Eigenvalue Formalism Phys. Rev. B 1986, 41, 7892-7895