Formation of imine oligomers on au under ambient conditions investigated by scanning tunneling microscopy

Langmuir

Volumn 29, Issue 2, 2013, Pages 653-657

  Greenwood, J ^a   Baddeley, C J ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMBIENT CONDITIONS; AU SURFACES; DEPOSITION FROM SOLUTIONS; NUCLEOPHILIC SUBSTITUTION REACTIONS; ROOM TEMPERATURE; SELF-ASSEMBLE; TIME-SCALES;

ALDEHYDES; MELAMINE; NITROGEN COMPOUNDS; OLIGOMERS; SCANNING TUNNELING MICROSCOPY; SUBSTITUTION REACTIONS;

SURFACE REACTIONS;

EID: 84872530533     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la304506s     Document Type: Article

References (32)

1. Theobald, J. A.; Oxtoby, N. S.; Phillips, M. A.; Champness, N. R.; Beton, P. H. Controlling molecular deposition and layer structure with supramolecular surface assemblies Nature 2003, 424, 1029-1031
2. Kudernac, T.; Lei, S.; Elemans, J. A. A. W.; De Feyter, S. Two-dimensional supramolecular self-assembly: nanoporous networks on surfaces Chem. Soc. Rev. 2009, 38, 402-421
3. Barth, J. V. Molecular architectonic on metal surfaces Annu. Rev. Phys. Chem. 2007, 58, 375-407
4. De Feyter, S.; De Schryver, F. C. Self-assembly at the liquid/solid interface: STM reveals J. Phys. Chem. B 2005, 109, 4290-4302
5. De Feyter, S.; Miura, A.; Yao, S.; Chen, Z.; Wurthner, F.; Jonkheijm, P.; Schenning, A.; Meijer, E. W.; De Schryver, F. C. Two-dimensional self-assembly into multicomponent hydrogen-bonded nanostructures Nano Lett. 2005, 5, 77-81
6. Cebula, I.; Shen, C.; Buck, M. Isophthalic acid: a basis for highly ordered monolayers Angew. Chem., Int. Ed. 2010, 49, 6220-6223
7. Silly, F.; Shaw, A. Q.; Castell, M. R.; Briggs, G. A. D.; Mura, M.; Martsinovich, N.; Kantorovich, L. Melamine structures on the Au(111) surface J. Phys. Chem. C 2008, 112, 11476-11480
8. Furukawa, S.; Tahara, K.; De Schryver, F. C.; Van der Auweraer, M.; Tobe, Y.; De Feyter, S. Structural transformation of a two-dimensional molecular network in response to selective guest inclusion Angew. Chem., Int. Ed. 2007, 46, 2831-2834
9. Blum, M. C.; Cavar, E.; Pivetta, M.; Patthey, F.; Schneider, W. D. Conservation of chirality in a hierarchical supramolecular self-assembled structure with pentagonal symmetry Angew. Chem., Int. Ed. 2005, 44, 5334-5337
10. Stepanow, S.; Lingenfelder, M.; Dmitriev, A.; Spillmann, H.; Delvigne, E.; Lin, N.; Deng, X. B.; Cai, C. Z.; Barth, J. V.; Kern, K. Steering molecular organization and host-guest interactions using two-dimensional nanoporous coordination systems Nat. Mater. 2004, 3, 229-233
11. Gourdon, A. On-surface covalent coupling in ultrahigh vacuum Angew. Chem., Int. Ed. 2008, 47, 6950-6953
12. 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
13. Lackinger, M.; Heckl, W. M. A STM perspective on covalent intermolecular coupling reactions on surfaces. J. Phys. D: Appl. Phys. 2011, 44.
14. Liang, H.; He, Y.; Ye, Y. C.; Xu, X. G.; Cheng, F.; Sun, W.; Shao, X.; Wang, Y. F.; Li, J. L.; Wu, K. Two-dimensional molecular porous networks constructed by surface assembling Coord. Chem. Rev. 2009, 253, 2959-2979
15. Weigelt, S.; Schnadt, J.; Tuxen, A. K.; Masini, F.; Bombis, C.; Busse, C.; Isvoranu, C.; Ataman, E.; Laegsgaard, E.; Besenbacher, F.; Linderoth, T. R. Formation of trioctylamine from octylamine on Au(111) J. Am. Chem. Soc. 2008, 130, 5388-5389
16. 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. (Cambridge, U. K.) 2008, 1536-1538
17. 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
18. Heim, D.; Ecija, D.; Seutert, K.; Auwaerter, W.; Aurisicchio, C.; Fabbro, C.; Bonifazi, D.; Barth, J. V. Self-assembly of flexible one-dimensional coordination polymers on metal surfaces J. Am. Chem. Soc. 2010, 132, 6783-6790
19. Weigelt, S.; Busse, C.; Bombis, C.; Knudsen, M. M.; Gothelf, K. V.; Strunskus, T.; Woll, C.; Dahlbom, M.; Hammer, B.; Laegsgaard, E.; Besenbacher, F.; Linderoth, T. R. Covalent interlinking of an aldehyde and an amine on a Au(111) surface in ultrahigh vacuum Angew. Chem., Int. Ed. 2007, 46, 9227-9230
20. Weigelt, S.; Bombis, C.; Busse, C.; Knudsen, M. M.; Gothelf, K. V.; Laegsgaard, E.; Besenbacher, F.; Linderoth, T. R. Molecular self-assembly from building blocks synthesized on a surface in ultrahigh vacuum: kinetic control and topo-chemical reactions ACS Nano 2008, 2, 651-660
21. Li, Y.; Wan, J.; Deng, K.; Han, X.; Lei, S.; Yang, Y.; Zheng, Q.; Zeng, Q.; Wang, C. Transformation of self-assembled structure by the addition of active reactant J. Phys. Chem. C 2011, 115, 6540-6544
22. 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
23. Treier, M.; Fasel, R.; Champness, N. R.; Argent, S.; Richardson, N. V. Molecular imaging of polyimide formation Phys. Chem. Chem. Phys. 2009, 11, 1209-1214
24. Treier, M.; Richardson, N. V.; Fasel, R. Fabrication of surface-supported low-dimensional polyimide networks J. Am. Chem. Soc. 2008, 130, 14054-14055
25. Schmitz, C. H.; Ikonomov, J.; Sokolowski, M. Two-dimensional ordering of poly(p-phenylene-terephthalamide) on the Ag(111) surface investigated by scanning tunneling microscopy J. Phys. Chem. C 2009, 113, 11984-11987
26. Schmitz, C. H.; Schmid, M.; Gaertner, S.; Steinrueck, H.-P.; Gottfried, J. M.; Sokolowski, M. Surface polymerization of poly(p-phenylene- terephthalamide) on Ag(111) investigated by X-ray photoelectron spectroscopy and scanning tunneling microscopy J. Phys. Chem. C 2011, 115, 18186-18194
27. Jensen, S.; Greenwood, J.; Früchtl, H. A.; Baddeley, C. J. STM Investigation on the formation of oligoamides on Au{111} by surface-confined reactions of melamine with trimesoyl chloride J. Phys. Chem. C 2011, 115, 8630-8636
28. Jensen, S.; Früchtl, H.; Baddeley, C. J. Coupling of triamines with diisocyanates on Au(111) leads to the formation of polyurea networks J. Am. Chem. Soc. 2009, 131, 16706-16713
29. 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
30. Chis, V.; Mile, G.; Stiufiuc, R.; Leopold, N.; Oltean, M. Vibrational and electronic structure of PTCDI and melamine-PTCDI complexes J. Mol. Struct. 2009, 924-26, 47-53
31. Perdigao, L. M. A.; Perkins, E. W.; Ma, J.; Staniec, P. A.; Rogers, B. L.; Champness, N. R.; Beton, P. H. Bimolecular networks and supramolecular traps on Au(111) J. Phys. Chem. B 2006, 110, 12539-12542
32. Hall, N. E.; Smith, B. J. High-level ab initio molecular orbital calculations of imine formation J. Phys. Chem. A 1998, 102, 4930-4938