Journal
SMALL
Volume 5, Issue 5, Pages 592-597Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/smll.200801943
Keywords
catalysis; conjugated polymers; STM; surface science; Ullmann coupling
Categories
Funding
- NSERC of Canada
- AFOSR
- AOARD
- U.S.A., the Petroleum Research Fund
- MDEIE (Quebec)
- DuPont Young Professor Award
- Canada Research Chairs program
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The surface-mediated synthesis of epitaxially aligned and separated polyphenylene lines on Cu(110) by exploiting the Ullmann dehalogenation reaction is reported. Scanning tunneling microscopy (STM) and X-ray photoelectron spectroscopy (XPS) show that the C-I bonds of 1,4-diiodobenzene and 1,3-diiodobenzene (C6H4I2) are catalytically cleaved when dosed onto the surface. Subsequent annealing transforms the copper-bound phenylene intermediates into covalent conjugated structures: linear chains of poly(p-phenylene) for 1,4-diiodobenzene and zigzag chains of poly(m-phenylene) as well as macrocyclic oligomers in the case of 1,3-diiodobenzene. The chains are strongly bound to the surface (likely through C-Cu bonds at the chain-ends) while the macrocycles are very mobile and can only be imaged by STM at low temperature. The detached halogens adsorb on the surface and separate the polymer chains front each other.
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