Unprecedented transformation of tetrathienoanthracene into pentacene on Ni(111)

ACS Nano

Volumn 7, Issue 2, 2013, Pages 1652-1657

  Dinca, Laurentiu E ^a   Fu, Chaoying ^b   MacLeod, Jennifer M ^a   Lipton Duffin, Josh ^a   Brusso, Jaclyn L ^b   Szakacs, Csaba E ^a   Ma, Dongling ^a   Perepichka, Dmitrii F ^b   Rosei, Federico ^a  

^a INRS EMT   (Canada)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

desulfurization; Ni(111); pentacene; SIMS; STM; thiophene

Indexed keywords

CHEMICAL PATHWAYS; CONTROLLED SYNTHESIS; CYCLIZATION REACTIONS; NANOSCALE TECHNOLOGIES; NI(111); ORGANIC MOLECULES; PENTACENES; SINGLE MOLECULE REACTION; STM; SUB-MOLECULAR RESOLUTION; TIME OF FLIGHT SECONDARY ION MASS SPECTROMETRY;

CYCLIZATION; DESULFURIZATION; MOLECULES; SCANNING TUNNELING MICROSCOPY; SECONDARY ION MASS SPECTROMETRY; THIOPHENE;

NICKEL;

EID: 84874413160     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn305572s     Document Type: Article

References (51)

1. Ritort, F. Single-Molecule Experiments in Biological Physics: Methods and Applications J. Phys.:Condens. Matter 2006, 18, R531-R583
2. Moerner, W. E.; Orrit, M. Illuminating Single Molecules in Condensed Matter Science 1999, 283, 1670-1676
3. Ho, W. Single-Molecule Chemistry J. Chem. Phys. 2002, 117, 11033-11061
4. Mehta, A. D.; Rief, M.; Spudich, J. A.; Smith, D. A.; Simmons, R. M. Single-Molecule Biomechanics with Optical Methods Science 1999, 283, 1689-1695
5. Kneipp, K.; Wang, Y.; Kneipp, H.; Perelman, L. T.; Itzkan, I.; Dasari, R. R.; Feld, M. S. Single Molecule Detection Using Surface-Enhanced Raman Scattering (SERS) Phys. Rev. Lett. 1997, 78, 1667-1670
6. Weiss, S. Fluorescence Spectroscopy of Single Biomolecules Science 1999, 283, 1676-1683
7. Gross, L.; Mohn, F.; Moll, N.; Liljeroth, P.; Meyer, G. The Chemical Structure of a Molecule Resolved by Atomic Force Microscopy Science 2009, 325, 1110-1114
8. Gross, L.; Mohn, F.; Moll, N.; Schuler, B.; Criado, A.; Guitián, E.; Peña, D.; Gourdon, A.; Meyer, G. Bond-Order Discrimination by Atomic Force Microscopy Science 2012, 337, 1326-1329
9. Wintterlin, J.; Völkening, S.; Janssens, T. V. W.; Zambelli, T.; Ertl, G. Atomic and Macroscopic Reaction Rates of a Surface-Catalyzed Reaction Science 1997, 278, 1931-1934
10. 3 Dissociation on Si(001) Phys. Rev. Lett. 1987, 59, 2071-2074
11. Hla, S.-W.; Bartels, L.; Meyer, G.; Rieder, K.-H. Inducing All Steps of a Chemical Reaction with the Scanning Tunneling Microscope Tip: Towards Single Molecule Engineering Phys. Rev. Lett. 2000, 85, 2777-2780
12. Rosei, F.; Schunack, M.; Naitoh, Y.; Jiang, P.; Gourdon, A.; Laegsgaard, E.; Stensgaard, I.; Joachim, C.; Besenbacher, F. Properties of Large Organic Molecules on Metal Surfaces Prog. Surf. Sci. 2003, 71, 95-146
13. Otero, R.; Rosei, F.; Besenbacher, F. Scanning Tunneling Microscopy Manipulation of Complex Organic Molecules on Solid Surfaces Annu. Rev. Phys. Chem. 2006, 57, 497-525
14. Cicoira, F.; Santato, C.; Rosei, F. Two-Dimensional Nanotemplates as Surface Cues for the Controlled Assembly of Organic Molecules Top. Curr. Chem. 2008, 285, 203-267
15. Palma, C.-A.; Samori, P. Blueprinting Macromolecular Electronics Nat. Chem. 2011, 3, 431-436
16. Perepichka, D. F.; Rosei, F. Extending Polymer Conjugation into the Second Dimension Science 2009, 323, 216-217
17. Grim, P. C. M.; De Feyter, S.; Gesquiere, A.; Vanoppen, P.; Rucker, M.; Valiyaveettil, S.; Moessner, G.; Mullen, K.; De Schryver, F. C. Submolecularly Resolved Polymerization of Diacetylene Molecules on the Graphite Surface Observed with Scanning Tunneling Microscopy Angew. Chem., Int. Ed. 1997, 36, 2601-2603
18. Okawa, Y.; Aono, M. Nanoscale Control of Chain Polymerization Nature 2001, 409, 683-684
19. Okawa, Y.; Aono, M. Linear Chain Polymerization Initiated by a Scanning Tunneling Microscope Tip at Designated Positions J. Chem. Phys. 2001, 115, 2317-2322
20. Sakaguchi, H.; Matsumura, H.; Gong, H. Electrochemical Epitaxial Polymerization of Single-Molecular Wires Nat. Mater. 2004, 3, 551-557
21. Sakaguchi, H.; Matsumura, H.; Gong, H.; Abouelwafa, A. M. Direct Visualization of the Formation of Single-Molecule Conjugated Copolymers Science 2005, 310, 1002-1006
22. 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 Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 11200-11204
23. Grill, L.; Dyer, M.; Lafferentz, L.; Persson, M.; Peters, M. V.; Hecht, S. Nano-architectures by Covalent Assembly of Molecular Building Blocks Nat. Nanotechnol. 2007, 2, 687-691
24. Lipton-Duffin, J. A.; Ivasenko, O.; Perepichka, D. F.; Rosei, F. Synthesis of Polyphenylene Molecular Wires by Surface-Confined Polymerization Small 2009, 5, 592-597
25. 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
26. Tanoue, R.; Higuchi, R.; Enoki, N.; Miyasato, Y.; Uemura, S.; Kimizuka, N.; Stieg, A. Z.; Gimzewski, J. K.; Kunitake, M. Thermodynamically Controlled Self-Assembly of Covalent Nanoarchitectures in Aqueous Solution ACS Nano 2011, 5, 3923-3929
27. Faury, T.; Clair, S.; Abel, M.; Dumur, F.; Gigmes, D.; Porte, L. Sequential Linking to Control Growth of a Surface Covalent Organic Framework J. Phys. Chem. C 2012, 116, 4819-4823
28. Zwaneveld, N. A. A.; Pawlak, R.; Abel, M.; Catalin, D.; Gigmes, D.; Bertin, D.; Porte, L. Organized Formation of 2d Extended Covalent Organic Frameworks at Surfaces J. Am. Chem. Soc. 2008, 130, 6678-6679
29. Dienstmaier, J. F.; Medina, D. D.; Dogru, M.; Knochel, P.; Bein, T.; Heckl, W. M.; Lackinger, M. Isoreticular Two-Dimensional Covalent Organic Frameworks Synthesized by on-Surface Condensation of Diboronic Acids ACS Nano 2012, 6, 7234-7242
30. Veld, M. I.; 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
31. Matena, M.; Riehm, T.; Stohr, 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
32. McCullough, R. D. The Chemistry of Conducting Polythiophenes Adv. Mater. 1998, 10, 93-116
33. Huntley, D. R.; Mullins, D. R.; Wingeier, M. P. Desulfurization of Thiophenic Compounds by Ni(111): Adsorption and Reactions of Thiophene, 3-Methylthiophene, and 2,5-Dimethylthiophene J. Phys. Chem. 1996, 100, 19620-19627
34. Ma, Z.; Zaera, F. Organic Chemistry on Solid Surfaces Surf. Sci. Rep. 2006, 61, 229-281
35. Varnam, A.; Sutherland, J. M. Beverages: Technology, Chemistry and Microbiology; Chapman & Hall: London, 1994; Vol. 2.
36. Collins, M. A.; Jones, D. N. A Total Synthesis of Estradiol and Its 6,6-Dimethyl Analogue Tetrahedron Lett. 1995, 36, 4467-4470
37. Marchalín, Š.; Žúžiová, J.; Kadlečíková, K.; Šafář, P.; Baran, P.; Dalla, V.; Daïch, A. An Expedient Synthesis of 7(S)-Ethyl-8(R or S)-Indolizidinols Based on a Thiophene Reductive Desulfurization Tetrahedron Lett. 2007, 48, 697-702
38. Anthony, J. E. Functionalized Acenes and Heteroacenes for Organic Electronics Chem. Rev. 2006, 106, 5028-5048
39. Gutzler, R.; Ivasenko, O.; Fu, C.; Brusso, J. L.; Rosei, F.; Perepichka, D. F. Halogen Bonds as Stabilizing Interactions in a Chiral Self-Assembled Molecular Monolayer Chem. Commun. 2011, 47, 9453-9455
40. Gutzler, R.; Fu, C.; Dadvand, A.; Hua, Y.; MacLeod, J. M.; Rosei, F.; Perepichka, D. F. Halogen Bonds in 2d Supramolecular Self-Assembly of Organic Semiconductors Nanoscale 2012, 4, 5965-5971
41. Maurice, V.; Kitakatsu, N.; Siegers, M.; Marcus, P. Low-Coverage Sulfur Induced Reconstruction of Ni(111) Surf. Sci. 1997, 373, 307-317
42. While sulfur is also known to form a (√3 × √3)R30 phase on Ni(111) (e.g., Perderea, M.; Oudar, J. Structure, Surf. Sci. 20, 80 (1970)), a bromine-based structure is more likely since the sulfur (√3 × √3)R30 phase is less stable than the observed rectangular reconstruction. Furthermore, we do not observe the (√3 × √3)R30 phase on surfaces exposed to the non-brominated 2TTA molecule.
43. Foresti, M. L.; Aloisi, G.; Innocenti, M.; Kobayashi, H.; Guidelli, R. Crystal Face Effects on Adsorption of Ionic and Non-ionic Species on Ag Electrodes: An Electrochemical and STM Study Surf. Sci. 1995, 335, 241-251
44. Jones, R. G.; Kadodwala, M. Bromine Adsorption on Cu(111) Surf. Sci. 1997, 370, L219-L225
45. Xu, H.; Yuro, R.; Harrison, I. The Structure and Corrosion Chemistry of Bromine on Pt(111) Surf. Sci. 1998, 411, 303-315
46. Kane, S. M.; Gland, J. L. Cyclohexanethiol Adsorption and Reaction on the Ni(111) Surface J. Phys. Chem. B 1998, 102, 5322-5328
47. Kane, S. M.; Rufael, T. S.; Gland, J. L.; Huntley, D. R.; Fischer, D. A. Role of Hydrogen in Benzene Formation from Benzenethiol on the Ni(111) Surface J. Phys. Chem. B 1997, 101, 8486-8491
48. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A., et al. Gaussian 09, revision B.01; Gaussian, Inc.: Wallingford CT, 2009.
49. Hanwell, M. D.; Curtis, D. E.; Lonie, D. C.; Vandermeersch, T.; Zurek, E.; Hutchison, G. R. Avogadro: An Advanced Semantic Chemical Editor, Visualization, and Analysis Platform J. Cheminf. 2012, 4, 17
50. Brusso, J. L.; Hirst, O. D.; Dadvand, A.; Ganesan, S.; Cicoira, F.; Robertson, C. M.; Oakley, R. T.; Rosei, F.; Perepichka, D. F. Two-Dimensional Structural Motif in Thienoacene Semiconductors: Synthesis, Structure, and Properties of Tetrathienoanthracene Isomers Chem. Mater. 2008, 20, 2484-2494
51. 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