Journal
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
Volume 107, Issue 25, Pages 11200-11204Publisher
NATL ACAD SCIENCES
DOI: 10.1073/pnas.1000726107
Keywords
metal-catalyzed coupling reaction; molecular wires; cis-polythiophene; scanning probe microscopy; polymerization mechanism
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Funding
- Natural Sciences and Engineering Research Council of Canada
- Air Force Office of Scientific Research
- Asian Office of Aerospace Research and Development of the USA
- American Chemical Society
- Ministere du Developpement economique, de l'Innovation et de l'Exportation of Quebec
- Fonds quebecois de la recherche sur la nature et les technologies Centre for Self-Assembled Chemical Structures
- DuPont
- Canada Research Chairs program
- Center for Nanophase Materials Sciences
- US Department of Energy, Office of Science, Office of Basic Energy Sciences [DE-SC0001087]
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One of the great challenges in surface chemistry is to assemble aromatic building blocks into ordered structures that are mechanically robust and electronically interlinked-i.e., are held together by covalent bonds. We demonstrate the surface-confined growth of ordered arrays of poly(3,4-ethylenedioxythiophene) (PEDOT) chains, by using the substrate (the 110 facet of copper) simultaneously as template and catalyst for polymerization. Copper acts as promoter for the Ullmann coupling reaction, whereas the inherent anisotropy of the fcc 110 facet confines growth to a single dimension. High resolution scanning tunneling microscopy performed under ultrahigh vacuum conditions allows us to simultaneously image PEDOT oligomers and the copper lattice with atomic resolution. Density functional theory calculations confirm an unexpected adsorption geometry of the PEDOToligomers, which stand on the sulfur atom of the thiophene ring rather than lying flat. This polymerization approach can be extended to many other halogen-terminated molecules to produce epitaxially aligned conjugated polymers. Such systems might be of central importance to develop future electronic and optoelectronic devices with high quality active materials, besides representing model systems for basic science investigations.
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