A reversible single-molecule switch based on activated antiaromaticity
Abstract
Single-molecule electronic devices provide researchers with an unprecedented ability to relate novel physical phenomena to molecular chemical structures. Typically, conjugated aromatic molecular backbones are relied upon to create electronic devices, where the aromaticity of the building blocks is used to enhance conductivity. We capitalize on the classical physical organic chemistry concept of Hückel antiaromaticity by demonstrating a single-molecule switch that exhibits low conductance in the neutral state and, upon electrochemical oxidation, reversibly switches to an antiaromatic high-conducting structure. We form single-molecule devices using the scanning tunneling microscope–based break-junction technique and observe an on/off ratio of ~70 for a thiophenylidene derivative that switches to an antiaromatic state with 6-4-6-p electrons. Through supporting nuclear magnetic resonance measurements, we show that the doubly oxidized core has antiaromatic character and we use density functional theory calculations to rationalize the origin of the high-conductance state for the oxidized single-molecule junction. Together, our work demonstrates how the concept of antiaromaticity can be exploited to create single-molecule devices that are highly conducting.
- Authors:
-
[1];
[2];
[1];
[4];
[2];
[4];
[5];
[1]
- Columbia Univ., New York, NY (United States). Dept. of Chemistry
- Columbia Univ., New York, NY (United States). Dept. of Applied Physics
- Fudan Univ., Shanghai (China)
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Molecular Foundry
- Columbia Univ., New York, NY (United States). Dept. of Chemistry; Columbia Univ., New York, NY (United States). Dept. of Applied Physics
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)
- OSTI Identifier:
- 1432216
- Grant/Contract Number:
- AC02-05CH11231
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Science Advances
- Additional Journal Information:
- Journal Volume: 3; Journal Issue: 10; Journal ID: ISSN 2375-2548
- Publisher:
- AAAS
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Yin, Xiaodong, Zang, Yaping, Zhu, Liangliang, Low, Jonathan Z., Liu, Zhen-Fei, Cui, Jing, Neaton, Jeffrey B., Venkataraman, Latha, and Campos, Luis M.. A reversible single-molecule switch based on activated antiaromaticity. United States: N. p., 2017.
Web. doi:10.1126/sciadv.aao2615.
Yin, Xiaodong, Zang, Yaping, Zhu, Liangliang, Low, Jonathan Z., Liu, Zhen-Fei, Cui, Jing, Neaton, Jeffrey B., Venkataraman, Latha, & Campos, Luis M.. A reversible single-molecule switch based on activated antiaromaticity. United States. https://doi.org/10.1126/sciadv.aao2615
Yin, Xiaodong, Zang, Yaping, Zhu, Liangliang, Low, Jonathan Z., Liu, Zhen-Fei, Cui, Jing, Neaton, Jeffrey B., Venkataraman, Latha, and Campos, Luis M.. Fri .
"A reversible single-molecule switch based on activated antiaromaticity". United States. https://doi.org/10.1126/sciadv.aao2615. https://www.osti.gov/servlets/purl/1432216.
@article{osti_1432216,
title = {A reversible single-molecule switch based on activated antiaromaticity},
author = {Yin, Xiaodong and Zang, Yaping and Zhu, Liangliang and Low, Jonathan Z. and Liu, Zhen-Fei and Cui, Jing and Neaton, Jeffrey B. and Venkataraman, Latha and Campos, Luis M.},
abstractNote = {Single-molecule electronic devices provide researchers with an unprecedented ability to relate novel physical phenomena to molecular chemical structures. Typically, conjugated aromatic molecular backbones are relied upon to create electronic devices, where the aromaticity of the building blocks is used to enhance conductivity. We capitalize on the classical physical organic chemistry concept of Hückel antiaromaticity by demonstrating a single-molecule switch that exhibits low conductance in the neutral state and, upon electrochemical oxidation, reversibly switches to an antiaromatic high-conducting structure. We form single-molecule devices using the scanning tunneling microscope–based break-junction technique and observe an on/off ratio of ~70 for a thiophenylidene derivative that switches to an antiaromatic state with 6-4-6-p electrons. Through supporting nuclear magnetic resonance measurements, we show that the doubly oxidized core has antiaromatic character and we use density functional theory calculations to rationalize the origin of the high-conductance state for the oxidized single-molecule junction. Together, our work demonstrates how the concept of antiaromaticity can be exploited to create single-molecule devices that are highly conducting.},
doi = {10.1126/sciadv.aao2615},
journal = {Science Advances},
number = 10,
volume = 3,
place = {United States},
year = {2017},
month = {10}
}
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Figures / Tables:
Fig. 1: Model of the electrochemically activated BTP switch. BTP shows the neutral, low-conductance state. Upon oxidation, BTP gains antiaromatic character to the 6-4-6-π electron state that exhibits high conductance.
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