Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 7, Pages 2136-2139Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja111320n
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Funding
- Nanoscale Science and Engineering Initiative of the NSF [CHE-0641523]
- New York State Office of Science and Technology
- Division of Chemical Sciences, Geosciences, and Biosciences of the U.S. Department of Energy [DE-FGO2-90ER14162]
- Packard Foundation
- Guthikonda family
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Understanding electron transport across pi-pi-stacked systems will help to answer fundamental questions about biochemical redox processes and benefit the design of new materials and molecular devices. Herein we employed the STM break-junction technique to measure the single-molecule conductance of multiple pi-pi-stacked aromatic rings. We studied electron transport through up to four stacked benzene rings held together in an eclipsed fashion via a paracyclophane scaffold. We found that the strained hydrocarbons studied herein couple directly to gold electrodes during the measurements; hence, we did not require any heteroatom binding groups as electrical contacts. Density functional theory-based calculations suggest that the gold atoms of the electrodes bind to two neighboring carbon atoms of the outermost cyclophane benzene rings in eta(2) fashion. Our measurements show an exponential decay of the conductance with an increasing number of stacked benzene rings, indicating a nonresonant tunneling mechanism. Furthermore, STM tip-substrate displacement data provide additional evidence that the electrodes bind to the outermost benzene rings of the pi-pi-stacked molecular wires.
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