Synthesis of polyphenylene molecular wires by surface-confined polymerization

Small

Volumn 5, Issue 5, 2009, Pages 592-597

  Lipton Duffin, J A ^a   Ivasenko, O ^b   Perepichka, D F ^b   Rosei, F ^a  

^a INRS EMT   (Canada)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

Catalysis; Conjugated polymers; STM; Surface science; Ullmann coupling

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; CONJUGATED POLYMERS; DEHALOGENATION; MOLECULAR SPECTROSCOPY; OLIGOMERS; POLYMERS; SCANNING TUNNELING MICROSCOPY; X RAY PHOTOELECTRON SPECTROSCOPY;

CHAIN-ENDS; CONJUGATED STRUCTURES; CU(110); DIIODOBENZENE; LINEAR CHAINS; LOW TEMPERATURES; MACROCYCLES; MACROCYCLIC OLIGOMERS; MOLECULAR WIRES; POLY (P-PHENYLENE); POLYMER CHAINS; POLYPHENYLENE; STM; SURFACE SCIENCE; ULLMANN COUPLING; X-RAY PHOTOELECTRON SPECTROSCOPIES; ZIGZAG CHAINS;

ORGANIC POLYMERS;

NANOTUBE; POLYMER; POLYPHENYLENE SULFIDE;

ARTICLE; CHEMISTRY; CONFORMATION; CRYSTALLIZATION; MACROMOLECULE; MATERIALS TESTING; METHODOLOGY; NANOTECHNOLOGY; PARTICLE SIZE; SURFACE PROPERTY; ULTRASTRUCTURE;

CRYSTALLIZATION; MACROMOLECULAR SUBSTANCES; MATERIALS TESTING; MOLECULAR CONFORMATION; NANOTECHNOLOGY; NANOTUBES; PARTICLE SIZE; POLYMERS; SURFACE PROPERTIES;

EID: 62749182817     PISSN: 16136810     EISSN: 16136829     Source Type: Journal    
DOI: 10.1002/smll.200801943     Document Type: Article

References (49)

1. T. A. Skotheim, J. R. Reynolds, Handbook of Conducting Polymers, 3rd ed., CRC Press, 2007.
2. a) D. F. Perepichka, F. Rosei, Science 2009, 323, 216;
3. b) N. R. Champness, Nat. Nanotech. 2007, 2, 671;
4. c) A. Gourdon, Angew. Chem. Int. Ed. 2008, 47, 6950.
5. a) H. Sakaguchi, H. Matsumura, H. Gong, Nat. Mater. 2004, 3, 551;
6. b) H. Sakaguchi, H. Matsumura, H. Gong, A. M. Abouelwafa, Science 2005, 310, 1002.
7. P. C. M. Grim, S. De Feyter, A. Gesquière, P. Vanoppen, M. Rücker, S. Valiyaveettil, G. Moessner, K. Müllen, F. C. De Schryver, Angew. Chem. Int. Ed. 1997, 36, 2601.
8. a) Y. Okawa, M. Aono, Nature 2001, 409, 683;
9. b) Y. Okawa, M. Aono, Surf. Sci. 2002, 514, 41.
10. a) M. Matena, T. Riehm, M. Stöhr, T. A. Jung, L. H. Gade, Angew. Chem. Int. Ed. 2008, 47, 2414;
11. b) S. Weigelt, C. Busse, C. Bombis, M. M. Knudsen, K. V. Gothelf, E. Lægsgaard, F. Besenbacher, T. R. Linderoth, Angew. Chem. Int. Ed. 2008, 47, 4406;
12. c) N. A. A. Zwaneveld, R. Pawlak, M. Abel, D. Catalin, D. Gigmes, D. Bertin, L. Porte, J. Am. Chem. Soc. 2008, 130, 6678.
13. a) L. Grill, M. Dyer, L. Lafferentz, M. Persson, M. V. Peters, S. Hecht, Nat. Nanotechnol. 2007, 2, 687;
14. b) M. Treier, R. Fasel, N. R. Champness, S. Argent, N. V. Richardson, PCCP 2009, DOI: 10.1039/b815544p;
15. c) M. Treier, N. V. Richardson, R. Fasel, J. Am. Chem. Soc. 2008, 130, 14054.
16. When this paper was in preparation, copper-Induced surface polymerization of porphyrins through dehydrogenatlon was reported, although the mechanism of this unusual reaction is not yet understood (M. I. Veld, P. Iavicoli, S. Haq, D. B. Amabilino, R. Raval, Chem. Comm. 2008, 1536).
17. F. Ullmann, J. Bielecki, Ber. Deutsch. Chem. Ges. 1901, 34, 2174.
18. P. E. Fanta, Synthesis-Stuttgart 1974, 9.
19. J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359.
20. E. C. H. Sykes, P. Han, S. A. Kandel, K. F. Kelly, G. S. McCarty, P. S. Weiss, Acc. Chem. Res. 2003, 36, 945.
21. S. W. Hla, L. Bartels, G. Meyer, K. H. Rieder, Phys. Rev. Lett. 2000, 85, 2777.
22. G. S. McCarty, P. S. Weiss, J. Phys. Chem. B 2002, 106, 8005.
23. G. S. McCarty, P. S. Weiss, J. Am. Chem. Soc. 2004, 126, 16772.
24. a) P. H. Citrin, P. Eisenberger, R. C. Hewitt, Surf. Sci. 1979, 89, 28;
25. b) B. V. Andryushechkin, K. N. Eltsov, V. M. Shevlyuga, Surf. Sci. 2005, 584, 278;
26. c) A. Migani, F. Illas, J. Phys. Chem. B 2006, 110, 11894.
27. J. Bushell, A. F. Carley, M. Coughlin, P. R. Davies, D. Edwards, D. J. Morgan, M. Parsons, J. Phys. Chem. B 2005, 109, 9556.
28. a) A. F. Carley, M. Coughlin, P. R. Davies, D. J. Morgan, M. W. Roberts, Surf. Sci. 2004, 555, L138;
29. b) I. Kovacs, F. Solymosi, J. Phys. Chem. B 1997, 101, 5397.
30. a) X. L. Zhou, F. Solymosi, P. M. Blass, K. C. Cannon, J. M. White, Surf. Sci. 1989, 219, 294;
31. b) X. L. Zhou, J. M. White, Catai Lett. 1989, 2, 375.
32. a) M. Doering, H. P. Rust, B. G. Briner, A. M. Bradshaw, Surf. Sci. 1998, 410, L736;
33. b) B. L Rogers, J. G. Shapter, M. Ford, Surf. Sci. 2004, 548, 29.
34. 1 = 3 × 3.61 Å). Thus less prominent lines in between bright ones sit above the furrows.
35. K. N. Baker, A. V. Fratini, T. Resch, H. C. Knachel, W. W. Adams, E. P. Socci, B. L. Farmer, Polymer 1993, 34, 1571.
36. The short polymer chains are surrounded by regions of copper iodide reconstructed c(2 × 2); some streaking in the image indicates species diffusing along the surface.
37. P. W. Rabideau, A. Sygula, R. K. Dhar, F. R. Fronczek, Chem. Commun. 1993, 1795.
38. The dynamic formation and straightening of the kinks (s-cis/trans isomerization) has been observed by successive scans over the same area (see Supporting Information) at RT. The satellite atoms in the vicinity of the kink are much brighter than those along the long branches, which are in turn brighter than iodines in neighbouring 1-c(2 × 2) regions (gray arrows in Figure 4). Mapping of the iodine ad-layer lattice shows that the satellite atoms in the vicinity of the kink sit over short-bridge sites of the Cu(110) lattice, rather than the H4 positions of the unkinked satellite atoms. Force-field relaxed geometry of the polymer chain in the iodine matrix exhibit multiple short C-H.. .l distances (≈3.2Å) suggesting polymer-Iodine interactions.
39. From a qualitative point of view, slightly more 1,3-phenylene units form chains than macrocycles. A conservative estimate points to a ratio of 60% PMP to 40% macrocycles. It is however challenging to accurately count the statistics because of the demonstrated high mobility of the macrocycles.
40. H. Irngartinger, L. Leiserowitz, M. J. Schmidt, Chem. Ber. Recl. 1970, 103, 1132.
41. J. A. Miwa, F. Cicoira, J. Lipton-Duffin, D. F. Perepichka, C. Santato, F. Rosei, Nanotechnology 2008, 19, 424021 and references therein.
42. a) S. C. Cohen, A. G. Massey, J. Organomet. Chem. 1967, 10, 471;
43. b) F. L. Hedberg, H. Rosenberg, J. Am. Chem. Soc. 1969, 91, 1258;
44. c) H. A. Staab, H. Braunling, K. Schneider, Chem. Ber. Reel. 1968, 101, 879.
45. Macrocycles are formed through the same mechanism as PMP, as long as the corresponding oligomer adopts an appropriate (open cycle) conformation. The latter requires the rotation of phenylene units (s-cis/trans isomerization). The dynamics of this isomerization (which is the first step of cyclization) is shown in the STM movie included in the Supporting Information.
46. M. Lackinger, S.Griessl, W. M. Heckl, M. Hietschold, J. Phys. Chem. B 2002, 106, 4482.
47. The end chains of PPP and PMP are thought to be directly bound to Cu, as is the precursor protopolymer. This is also consistent with the macrocycles being significantly more mobile on the surface at RT than the PMP and PPP structures; therefore their bonding to the surface is inferred to be weaker (physisorption).
48. I. Horcas, R. Fernandez, J. M. Gomez-Rodriguez, J. Colchero, J. Gomez-Herrero, A. M. Baro, Rev. Sci. Instrum. 2007, 78, 8.
49. Gaussian 03, Revision D.01, M. J. Frisch, G. W. Trucks, H. B. Schiegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Closlowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, 2004.