Citation: Leng Xin-Li, Song Li-Li, Lu Yan, Liu Xiao-Qing, Wang Li. Observations of carbon-carbon coupling of 4, 4-dibromo-pterphenyl on Cu (110) surface at molecular level[J]. Chinese Chemical Letters, ;2017, 28(1): 24-28. doi: 10.1016/j.cclet.2016.06.036 shu

Observations of carbon-carbon coupling of 4, 4-dibromo-pterphenyl on Cu (110) surface at molecular level

Leng Xin-Li ^a ,
Song Li-Li ^b ,
Lu Yan ^a ,
Liu Xiao-Qing ^a,, ,
Wang Li ^a

a.
Department of Physics, Nanchang University, Nanchang 330031, China
b.
Department of Chemistry, Nanchang University, Nanchang 330031, China

Corresponding author: Liu Xiao-Qing, liuxiaoqing@ncu.edu.cn
Received Date: 25 May 2016
Revised Date: 14 June 2016
Accepted Date: 24 June 2016
Available Online: 2 January 2016

Figures(3)

The carbon-carbon couplings of 4, 4"-dibromo-p-terphenyl (DBTP) on Cu (110) surface have been investigated at a single molecular level by scanning tunneling microscopy. After annealing at 353 K, a mixture of parallel non-organometallic and organometallic intermediates of DBTP molecules along the[1-10] direction of the surface has been observed. Further annealing at 393 K causes one group of molecules to form oligomers with para-para and para-meta motifs via Ullmann reaction and the other group of molecules to synthesize oligomers with meta-meta motifs via direct carbon-carbon coupling reaction. Statistical results directly reveal that the occurrence of reaction type is strongly related to the initial binding configuration of DBTP molecules.
- Carbon-carbon coupling,
- Ullmann coupling,
- Organometallic intermediate,
- Selective C-H activation,
- Oligomer
1. [1]
  Classen T., Fratesi G., Costantini G.. Templated growth of metal-organic coordination chains at surfaces[J]. Angew. Chem. Int. Ed., 2005,44:6142-6145. doi: 10.1002/(ISSN)1521-3773
2. [2]
  Heim D., Seufert K., Auwä rter W.. Surface-assisted assembly of discrete porphyrin-based cyclic supramolecules[J]. Nano Lett., 2010,10:122-128. doi: 10.1021/nl9029994
3. [3]
  Yang H.H., Chu Y.H., Lu C.I.. Digitized charge transfer magnitude determined by metal-organic coordination number[J]. ACS Nano, 2013,7:2814-2819. doi: 10.1021/nn4003715
4. [4]
  Wang W.H., Shi X.Q., Wang S.Y.. Cooperative modulation of electronic structures of aromatic molecules coupled to multiple metal contacts[J]. Phys. Rev. Lett., 2013,110046802.. doi: 10.1103/PhysRevLett.110.046802
5. [5]
  Xiang F.F., Li C., Wang Z.P.. Direct observation of copper-induced metalation of 5, 15-diphenylporphyrin on Au (111) by scanning tunneling microscopy[J]. Surf. Sci., 2015,633:46-52. doi: 10.1016/j.susc.2014.11.021
6. [6]
  Shi Z.L., Lin N.. Porphyrin-based two-dimensional coordination Kagome lattice self-assembled on a Au (111) surface[J]. J. Am. Chem. Soc., 2009,131:5376-5377. doi: 10.1021/ja900499b
7. [7]
  Haq S., Hanke F., Dyer M.S.. Clean coupling of unfunctionalized porphyrins at surfaces to give highly oriented organometallic oligomers[J]. J. Am. Chem. Soc., 2011,133:12031-12039. doi: 10.1021/ja201389u
8. [8]
  Fan Q.T., Wang C.C., Han Y.. Surface-assisted organic synthesis of hyperbenzene nanotroughs[J]. Angew. Chem. Int. Ed., 2013,52:4668-4672. doi: 10.1002/anie.201300610
9. [9]
  Lafferentz L., Eberhardt V., Dri C.. Controlling on-surface polymerization by hierarchical and substrate-directed growth[J]. Nat. Chem., 2012,4:215-220. doi: 10.1038/nchem.1242
10. [10]
  Grill L., Dyer M., Lafferentz L.. Nano-architectures by covalent assembly of molecular building blocks[J]. Nat. Nanotechnol., 2007,2:687-691. doi: 10.1038/nnano.2007.346
11. [11]
  Pinardi A.L., Otero G., Irurueta -, Palacio I.. Tailored formation of N-doped nanoarchitectures by diffusion-controlled on-surface (cyclo) dehydrogenation of heteroaromatics[J]. ACS Nano, 2013,7:3676-3684. doi: 10.1021/nn400690e
12. [12]
  Treier M., Pignedoli C.A., Laino T.. Surface-assisted cyclodehydrogenation provides a synthetic route towards easily processable and chemically tailored nanographenes[J]. Nat. Chem., 2011,3:61-67. doi: 10.1038/nchem.891
13. [13]
  Wiengarten A., Seufert K., Auw W., rter ä. Surface-assisted dehydrogenative homocoupling of porphine molecules[J]. J. Am. Chem. Soc., 2014,136:9346-9354. doi: 10.1021/ja501680n
14. [14]
  Sun Q., Zhang C., Li Z.W.. On-surface formation of one-dimensional polyphenylene through Bergman cyclization[J]. J. Am. Chem. Soc., 2013,135:8448-8451. doi: 10.1021/ja404039t
15. [15]
  Xiang F.F., Lu Y., Li C.. Cyclotrimerization-induced chiral supramolecular structures of 4-ethynyltriphenylamine on Au (111) surface[J]. Chem. Eur. J., 2015,21:12978-12983. doi: 10.1002/chem.201501434
16. [16]
  Chen S.P., Sun Y., Wan S.B., Jiang T.. Facile synthesis of a 4-anilinoquinazoline dimer by Suzuki cross-coupling reaction[J]. Chin. Chem. Lett., 2011,22:1033-1035. doi: 10.1016/j.cclet.2011.01.013
17. [17]
  Liu C., Liu C., Li X.M., Gao Z.M., Jin Z.L.. Oxygen-promoted Pd/C-catalyzed Suzuki-Miyaura reaction of potassium aryltrifluoroborates[J]. Chin. Chem. Lett., 2016,27:631-634. doi: 10.1016/j.cclet.2015.12.022
18. [18]
  Zhang W.S., Xu W.J., Zhang F., Qu G.R.. Synthesis of symmetrical 1, 3-diynes via tandem reaction of (Z)-arylvinyl bromides in the presence of DBU and CuI[J]. Chin. Chem. Lett., 2013,24:407-410. doi: 10.1016/j.cclet.2013.03.016
19. [19]
  Zhou L., Xu Q.X., Jiang H.F.. Palladium-catalyzed homo-coupling of boronic acids with supported reagents in supercritical carbon dioxide[J]. Chin. Chem. Lett., 2007,18:1043-1046. doi: 10.1016/j.cclet.2007.06.023
20. [20]
  Sun Q., Cai L.L., Ding Y.Q.. Dehydrogenative homocoupling of terminal alkenes on copper surfaces:a route to dienes[J]. Angew. Chem. Int. Ed., 2015,54:4549-4552. doi: 10.1002/anie.201412307
21. [21]
  Sun Q., Zhang C., Kong H.H., Tan Q.G., Xu W.. On-surface aryl-aryl coupling via selective C-H activation[J]. Chem. Commun., 2014,50:11825-11828. doi: 10.1039/C4CC05482B
22. [22]
  Bombis C., Ample F., Lafferentz L.. Single molecular wires connecting metallic and insulating surface areas[J]. Angew. Chem. Int. Ed., 2009,48:9966-9970. doi: 10.1002/anie.v48:52
23. [23]
  Di Giovannantonio M., El Garah M., Lipton-Duffin J.. Insight into organometallic intermediate and its evolution to covalent bonding in surface-confined Ullmann polymerization[J]. ACS Nano, 2013,7:8190-8198. doi: 10.1021/nn4035684
24. [24]
  Lafferentz L., Ample F., Yu H.. Conductance of a single conjugated polymer as a continuous function of its length[J]. Science, 2009,323:1193-1197. doi: 10.1126/science.1168255
25. [25]
  Lipton-Duffin J.A., Ivasenko O., Perepichka D.F., Rosei F.. Synthesis of polyphenylene molecular wires by surface-confined polymerization[J]. Small, 2009,5:592-597. doi: 10.1002/smll.v5:5
26. [26]
  Wang W.H., Shi X.Q., Wang S.Y., Van Hove M.A., Lin N.. Single-molecule resolution of an organometallic intermediate in a surface-supported Ullmann coupling reaction[J]. J. Am. Chem. Soc., 2011,133:13264-13267. doi: 10.1021/ja204956b
27. [27]
  Basagni A., Sedona F., Pignedoli C.A.. Molecules-oligomers-nanowiresgraphene nanoribbons:a bottom-up stepwise on-surface covalent synthesis preserving long-range order[J]. J. Am. Chem. Soc., 2015,137:1802-1808. doi: 10.1021/ja510292b
28. [28]
  Cai J.M., Ruffieux P., Jaafar R.. Atomically precise bottom-up fabrication of graphene nanoribbons[J]. Nature, 2010,466:470-473. doi: 10.1038/nature09211
29. [29]
  Talirz L., Söde H., Cai J.M.. Termini of bottom-up fabricated graphene nanoribbons[J]. J. Am. Chem. Soc., 2013,135:2060-2063. doi: 10.1021/ja311099k
30. [30]
  Bieri M., Treier M., Cai J.M.. Porous graphenes:two-dimensional polymer synthesis with atomic precision[J]. Chem. Commun., 2009:6919-6921.
31. [31]
  Blunt M.O., Russell J.C., Champness N.R., Beton P.H.. Templating molecular adsorption using a covalent organic framework[J]. Chem. Commun., 2010,46:7157-7159. doi: 10.1039/c0cc01810d
32. [32]
  Gutzler R., Walch H., Eder G.. Surface mediated synthesis of 2D covalent organic frameworks:1, 3, 5-tris (4-bromophenyl) benzene on graphite (001), Cu (111), and Ag (110)[J]. Chem. Commun., 2009:4456-4458.
33. [33]
  Bieri M., Nguyen M.T., Gröning O.. Two-dimensional polymer formation on surfaces:insight into the roles of precursor mobility and reactivity[J]. J. Am. Chem. Soc., 2010,132:16669-16676. doi: 10.1021/ja107947z
34. [34]
  Shi K.J., Yuan D.W., Wang C.X.. Ullmann reaction of aryl chlorides on various surfaces and the application in stepwise growth of 2D covalent organic frameworks[J]. Org. Lett., 2016,18:1282-1285. doi: 10.1021/acs.orglett.6b00172
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