Supramolecular engineering through temperature-induced chemical modification of 2h-tetraphenylporphyrin on Ag(111): Flat phenyl conformation and possible dehydrogenation reactions

Chemistry - A European Journal

Volumn 17, Issue 51, 2011, Pages 14354-14359

  Di Santo, Giovanni ^a   Blankenburg, Stephan ^b   Castellarin Cudia, Carla ^a   Fanetti, Mattia ^a   Borghetti, Patrizia ^c   Sangaletti, Luigi ^c   Floreano, Luca ^d   Verdini, Alberto ^d   Magnano, Elena ^d   Bondino, Federica ^d   Pignedoli, Carlo A ^b   Nguyen, Manh Thuong ^b   Gaspari, Roberto ^b   Passerone, Daniele ^b   Goldoni, Andrea ^a  

^a INSTM Micro and Nano Carbon Laboratory   (Italy)

^b SWISS FEDERAL LABORATORIES FOR MATERIALS SCIENCE AND TECHNOLOGY   (Switzerland)

^c UNIVERSITÀ CATTOLICA DEL SACRO CUORE   (Italy)

^d LABORATORIO TASC   (Italy)

Author keywords

C C activation; density functional calculations; porphyrinoids; scanning probe microscopy; X ray spectroscopy

Indexed keywords

C-C ACTIVATIONS; DEHYDROGENATION REACTIONS; DENSITY-FUNCTIONAL CALCULATIONS; DFT CALCULATION; PHENYL RINGS; PORPHYRINOIDS; ROOM TEMPERATURE; SCANNING PROBES; SUPRAMOLECULAR ENGINEERING; TEMPERATURE-INDUCED; TETRAPHENYLPORPHYRINS;

CHEMICAL MODIFICATION; DEHYDROGENATION; DENSITY FUNCTIONAL THEORY; MONOLAYERS; SCANNING PROBE MICROSCOPY; X RAY SPECTROSCOPY;

CONFORMATIONS;

EID: 83755207721     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102268     Document Type: Article

References (39)

1. B. D. Berezin, Coordination Compounds of Porphyrins and Phthalocyanines, Wiley, Chichester, 1981.
2. J. E. Falk, Porphyrins and Metalloporphyrins: Their General, Physical and Coordination Chemistry, and Laboratory Methods, Elsevier, Amsterdam, 1964.
3. M. Bernien, J. Miguel, C. Weis, Md. E. Ali, J. Kurde, B. Krumme, P. M. Panchmatia, B. Sanyal, M. Piantek, P. Srivastava, K. Baberschke, P. M. Oppeneer, V. O. Eriksson, W. Kuch, H. Wende, Phys. Rev. Lett. 2009, 102, 047202.
4. M. Turner, O. P. H. Vaughan, G. Kyriakou, D. J. Watson, L. J. Scherer, A. C. Papageorgiou, J. K. M. Sanders, R. M. Lambert, J. Am. Chem. Soc. 2009, 131, 14913.
5. X. Huang, K. Nakanishi, N. Berova, Chirality 2000, 12, 237
6. I. J. MacDonald, T. J. Dougherty, J. Porphyrins Phthalocyanines 2001, 5, 105.
7. W. Auwärter, A. Weber-Bargioni, S. Brink, A. Riemann, A. Schiffrin, M. Ruben, J. V. Barth, ChemPhysChem 2007, 8, 250.
8. F. Buchner, V. Schwald, K. Comanici, H.-P. Steinruck, H. Marbach, ChemPhysChem 2007, 8, 241
9. A. M.-M. Kretschmann, M. Walz, K. Flechtner, H.-P. Steinruck, J. M. Gottfried, Chem. Commun. 2007, 568.
10. J. M. Gottfried, K. Flechtner, A. Kretschmann, T. Lukasczyk, H.-P. Steinruck, J. Am. Chem. Soc. 2006, 128, 5644.
11. Y. Bai, F. Buchner, I. Kellner, M. Schmid, F. Vollnhals, H.-P. Steinruck, H. Marbach, J. M. Gottfried, New J. Phys. 2009, 11, 125004.
12. F. Buchner, K. Flechtner, Y. Bai, E. Zillner, I. Kellner, H.-P. Steinruck, H. Marbach, J. M. Gottfried, J. Phys. Chem. C 2008, 112, 15458.
13. T. Lukasczyk, K. Flechtner, L. Merte, N. Jux, F. Maier, J. M. Gottfried, H.-P. Steinruck, J. Phys. Chem. C 2007, 111, 3090.
14. W. Auwärter, K. Seufert, F. Klappenberger, J. Reichert, A. Weber-Bargioni, A. Verdini, D. Cvetko, M. Dell'Angela, L. Floreano, A. Cossaro, G. Bavdek, A. Morgante, A. P. Seitsonen, J. V. Barth, Phys. Rev. B 2010, 81, 245403.
15. J. Stöhr, NEXAFS Spectroscopy, Springer, Berlin, 1996
16. C. Castellarin-Cudia, P. Vilmercati, R. Larciprete, C. Cepek, G. Zampieri, L. Sangaletti, S. Pagliara, A. Verdini, A. Cossaro, L. Floreano, A. Morgante, L. Petaccia, S. Lizzit, C. Battocchio, G. Polzonetti, A. Goldoni, Surf. Sci. 2006, 600, 4013.
17. H. L. Anderson, Chem. Commun. 1999, 2323.
18. F. Moresco, G. Meyer, K.-H. Rieder, J. Ping, H. Tang, C. Joachim, Surf. Sci. 2002, 499, 94
19. W. Auwärter, F. Klappenberger, A. Weber-Bargioni, A. Schiffrin, T. Strunskus, C. Woll, Y. Pennec, A. Riemann, J. V. Barth, J. Am. Chem. Soc. 2007, 129, 11279.
20. Ch. Loppacher, M. Guggisberg, O. Pfeiffer, E. Meyer, M. Bammerlin, R. Lüthi, R. Schlittler, J. K. Gimzewski, H. Tang, C. Joachim, Phys. Rev. Lett. 2003, 90, 066107.
21. M. Häming, C. Scheuermann, A. Schöll, F. Reinert, E. Umbach, J. Electron Spectrosc. Relat. Phenom. 2009, 174, 59.
22. J. C. Grossman, E. Schwegler, E. W. Draeger, F. Gygi, G. J. Galli, J. Chem. Phys. 2004, 120, 300
23. P. H.-L. Sit, N. J. Marzari, J. Chem. Phys. 2005, 122, 204510
24. J. VandeVondele, F. Mohamed, M. Krack, J. Hutter, M. Sprik, M. J. Parrinello, J. Chem. Phys. 2005, 122, 014515
25. S. B. Rempe, T. R. Mattsson, K. Leung, Phys. Chem. Chem. Phys. 2008, 10, 4685.
26. M. Treier, C. A. Pignedoli, T. Laino, R. Rieger, K. Müllen, D. Passerone, R. Fasel, Nat. Chem. 2011, 3, 61.
27. G. Di Santo, C. Castellarin-Cudia, M. Fanetti, B. Taleatu, P. Borghetti, L. Sangaletti, L. Floreano, E. Magnano, F. Bondino, A. Goldoni, J. Phys. Chem. C 2011, 115, 4155.
28. J. Cai, P. Ruffieux, R. Jaafar, M. Bieri, T. Braun, S. Blankenburg, M. Muoth, A. P. Seitsonen, M. Saleh, X. Feng, K. Mullen, R. Fasel, Nature 2010, 466, 470.
29. S. Haq, F. Hanke, M. S. Dyer, M. Persson, P. Iavicoli, D. B. Amabilino, R. Raval, J. Am. Chem. Soc. 2011, 133, 12031.
30. J. VandeVondele, M. Krack, F. Mohamed, M. Parrinello, T. Chassaing, J. Hutter, Comp. Phys. Comm. 2005, 167, 103.
31. J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865.
32. S. Goedecker, M. Teter, J. Hutter, Phys. Rev. B 1996, 54, 1703.
33. S. Grimme, J. Comput. Chem. 2006, 27, 1787.
34. C. A. Pignedoli, T. Laino, M. Treier, R. Fasel, D. Passerone, Eur. Phys. J. B 2010, 75, 65.
35. G. Bussi, D. Donadio, M. Parrinello, J. Chem. Phys. 2007, 126, 014101.
36. J. Tersoff, D. R. Hamann, Phys. Rev. B 1985, 31, 805.
37. J. C. Chen, Phys. Rev. B 1990, 42, 8841.
38. L. Floreano, G. Naletto, D. Cvetko, R. Gotter, M. Malvezzi, L. Marassi, A. Morgante, A. Santaniello, A. Verdini, F. Tommasini, G. Tondello, Rev. Sci. Instrum. 1999, 70, 3855.
39. L. Floreano, A. Cossaro, R. Gotter, A. Verdini, G. Bavdek, F. Evangelista, A. Ruocco, A. Morgante, D. Cvetko, J. Phys. Chem. C 2008, 112, 10794.