Clean coupling of unfunctionalized porphyrins at surfaces to give highly oriented organometallic oligomers

Journal of the American Chemical Society

Volumn 133, Issue 31, 2011, Pages 12031-12039

  Haq, Sam ^a   Hanke, Felix ^a   Dyer, Matthew S ^a   Persson, Mats ^a,b   Iavicoli, Patrizia ^c   Amabilino, David B ^c   Raval, Rasmita ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

^c INSTITUT DE CIÈNCIA DE MATERIALS DE BARCELONA ICMAB CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BUILDING BLOCKES; C-H BOND; COPPER ATOMS; CRYSTALLOGRAPHIC DIRECTIONS; DIRECT COUPLING; DIRECTIONAL COUPLING; EDGE-TO-EDGE; FUNCTIONALIZATIONS; GASEOUS HYDROGEN; HIGH TEMPERATURE; IN-SITU SCANNING TUNNELING MICROSCOPIES; MOLECULAR BUILDING BLOCKS; MOLECULAR DEVICE; MOLECULAR SYSTEMS; ORGANIC COMPONENTS; ORGANIC MOLECULES; ORGANIC NANOSTRUCTURES; PORPHYRIN MOLECULES; ROAD-MAPS; SINGLE CRYSTAL COPPER; SINGLE-STEP SYNTHESIS; SOLUTION CHEMISTRY; SURFACE CONTAMINATIONS; SURFACE-BASED; THEORETICAL MODELING;

HYDROGEN; NANOSTRUCTURES; OLIGOMERS; ORGANOMETALLICS; PORPHYRINS; SCANNING TUNNELING MICROSCOPY; SINGLE CRYSTALS; SYNTHESIS (CHEMICAL); TEMPERATURE PROGRAMMED DESORPTION; WIRE;

SURFACE REACTIONS;

AROMATIC COMPOUND; COPPER; HYDROGEN; NANOMATERIAL; OLIGOMER; ORGANOMETALLIC COMPOUND; PORPHYRIN DERIVATIVE;

ARTICLE; CROSS COUPLING REACTION; DESORPTION; HYDROGEN BOND; TEMPERATURE MEASUREMENT; THEORETICAL MODEL;

EID: 79961155070     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja201389u     Document Type: Article

References (47)

1. Maruccio, G.; Cingolani, R.; Rinaldi, R. J. Mater. Chem. 2004, 14, 542-554
2. Scheybal, A.; Ramsvik, T.; Bertschinger, R.; Putero, M.; Nolting, F.; Jung, T. A. Chem. Phys. Lett. 2005, 411, 214-220
3. Rapenne, G.; Launay, J. P.; Joachim, C. J. Phys.: Condens. Matter 2006, 18, S1797-S1808
4. Shirai, Y.; Morin, J. F.; Sasaki, T.; Guerrero, J. M.; Tour, J. M. Chem. Soc. Rev. 2006, 35, 1043-1055
5. Kim, W. Y.; Choi, Y. C.; Kim, K. S. J. Mater. Chem. 2008, 18, 4510-4521
6. Diez-Perez, I.; Hihath, J.; Lee, Y.; Yu, L. P.; Adamska, L.; Kozhushner, M. A.; Oleynik, I. I.; Tao, N. J. Nat. Chem. 2009, 1, 635-641
7. Mannini, M.; Pineider, F.; Sainctavit, P.; Danieli, C.; Otero, E.; Sciancalepore, C.; Talarico, A. M.; Arrio, M. A.; Cornia, A.; Gatteschi, D.; Sessoli, R. Nat. Mater. 2009, 8, 194-197
8. Lobo-Checa, J.; Matena, M.; Müller, K.; Dil, J. H.; Meier, F.; Osterwalder, J.; Gade, L. H.; Jung, T. A.; Stöhr, M. Science 2009, 325, 300-303
9. Grill, L.; Dyer, M.; Lafferentz, L.; Persson, M.; Peters, M. V.; Hecht, S. Nat. Nanotechnol. 2007, 2, 687-691
10. Int Veld, M.; Iavicoli, P.; Haq, S.; Amabilino, D. B.; Raval, R. Chem. Commun. 2008, 1536-1538
11. Weigelt, S.; Busse, C.; Bombis, C.; Knudsen, M. M.; Gothelf, K. V.; Lgsgaard, E.; Besenbacher, F.; Linderoth, T. R. Angew. Chem., Int. Ed. 2008, 47, 4406-4410
12. Lipton-Duffin, J. A.; Ivasenko, O.; Perepichka, D. F.; Rosei, F. Small 2009, 5, 592-597
13. Cai, J.; Ruffieux, P.; Jaafar, R.; Bieri, M.; Braun, T.; Blankenburg, S.; Muoth, M.; Seitsonen, A. P.; Saleh, M.; Feng, X.; Mullen, K.; Fasel, R. Nature 2010, 466, 470-473
14. Matena, M.; Stöhr, M.; Riehm, T.; Björk, J.; Martens, S.; Dyer, M. S.; Persson, M.; Lobo-Checa, J.; Müller, K.; Enache, M.; Wadepohl, H.; Zegenhagen, J.; Jung, T. A.; Gade, L. H. Chem.- Eur. J. 2010, 16, 2079-2091
15. We note that the terms 'organometallic compound and 'coordination-metal compounds are often used interchangeably in the surface science literature. In this paper, we utilize the formal definition of organometallic as only referring to compounds containing carbon-metal bonds, while metal-coordination compounds refer to metal connections with other (hetero)atoms (notably N, O, etc.).
16. Classen, T.; Lingenfelder, M.; Wang, Y.; Chopra, R.; Virojanadara, C.; Starke, U.; Costantini, G.; Fratesi, G.; Fabris, S.; de Gironcoli, S.; Baroni, S.; Haq, S.; Raval, R.; Kern, K. J. Phys. Chem. A 2007, 111, 12589-12603
17. Heim, D.; Seufert, K.; Auwärter, W.; Aurisicchio, C.; Fabbro, C.; Bonifazi, D.; Barth, J. V. Nano Lett. 2009, 10, 122-128
18. Fendt, L.-A.; Stöhr, M.; Wintjes, N.; Enache, M.; Jung, T. A.; Diederich, F. Chem.- Eur. J. 2009, 15, 11139-11150
19. Heim, D.; Écija, D.; Seufert, K.; Auwärter, W.; Aurisicchio, C.; Fabbro, C.; Bonifazi, D.; Barth, J. V. J. Am. Chem. Soc. 2010, 132, 6783-6790
20. Marschall, M.; Reichert, J.; Weber-Bargioni, A.; Seufert, K.; Auwarter, W.; Klyatskaya, S.; Zoppellaro, G.; Ruben, M.; Barth, J. V. Nat. Chem. 2010, 2, 131-137
21. Liljeroth, P.; Swart, I.; Paavilainen, S.; Repp, J.; Meyer, G. Nano Lett. 2010, 10, 2475-2479
22. Bartels, L. Nat. Chem. 2010, 2, 87-95
23. Osuka, A.; Shimidzu, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 135-137
24. Tsuda, A.; Furuta, H.; Osuka, A. J. Am. Chem. Soc. 2001, 123, 10304-10321
25. Tsuda, A.; Osuka, A. Science 2001, 293, 79-82
26. Kim, D; Osuka, A. Acc. Chem. Res. 2004, 37, 735-745
27. Abd-El-Aziz, S.; Shipman, P. O.; Boden, B. N.; McNeil, W. S. Prog. Polym. Sci. 2010, 35, 714-836
28. Hornig, S.; Manners, I.; Newkome, G. R.; Schubert, U. S. Macromol. Rapid Commun. 2010, 31, 771-771
29. Krause, N., Ed.; Modern Organocopper Chemistry: Wiley-VCH: Weinheim, Germany, 2002.
30. Lin, V. S. Y.; Iovine, P. M.; DiMagno, S. G.; Therien, M. J. Org. Synth. 2002, 33, 55-61
31. Kresse, G.; Furthmüller, J. Phys. Rev. B 1996, 54, 11169
32. Kresse, G.; Joubert, D. Phys. Rev. B 1999, 59, 1758
33. Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R.; Singh, D. J.; Fiolhais, C. Phys. Rev. B 1992, 46, 6671
34. Tersoff, J.; Hamann, D. R. Phys. Rev. Lett. 1983, 50, 1998
35. Lorente, N.; Persson, M. Faraday Discuss. 2000, 117, 277
36. Lindsey, J. S. Acc. Chem. Res. 2010, 43, 300-311
37. Severance, S.; Hamza, I. Chem. Rev. 2009, 109, 4596-4616
38. Mohnani, S.; Bonifazi, D. Coord. Chem. Rev. 2010, 254, 2342-2362
39. Di Natale, C.; Monti, D.; Paolesse, R. Mater. Today 2010, 13, 37-43
40. Latter, M. J.; Langford, S. J. Int. J. Mol. Sci. 2010, 11, 1878-1887
41. Gassman, P. G.; Ghosh, A.; Almlöf, J. J. Am. Chem. Soc. 1992, 114, 9990-10000
42. Schlözer, R.; Fuhrhop, J.-H. Angew. Chem., Int. Ed. Engl. 1975, 14, 363
43. Cramariuc, O.; Hukka, T. I.; Rantala, T. P. Chem. Phys. 2004, 305, 13-26
44. Dyer, M. S.; Robin, A.; Haq, S.; Raval, R.; Persson, M.; Klimes, J. ACS Nano 2011, 5, 1831-1838
45. Donovan, P.; Robin, A.; Dyer, M. S.; Persson, M.; Raval, R. Chem.- Eur. J. 2010, 16, 11641-11652
46. Davies, H. M. L.; Du Bois, J.; Yu, J. Q. Chem. Soc. Rev. 2011, 40, 1855-1856
47. Senge, M. O.; Davis, M. J. Porphyrins Phthalocyanines 2010, 14, 557-567