Highly-conducting molecular circuits based on antiaromaticity

Shintaro Fujii (), Santiago Marqués-González, Ji-Young Shin, Hiroshi Shinokubo (), Takuya Masuda, Tomoaki Nishino, Narendra P. Arasu, Héctor Vázquez () and Manabu Kiguchi ()
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Shintaro Fujii: Graduate School of Science and Engineering, Tokyo Institute of Technology, Ookayama
Santiago Marqués-González: Graduate School of Science and Engineering, Tokyo Institute of Technology, Ookayama
Ji-Young Shin: Graduate School of Engineering, Nagoya University
Hiroshi Shinokubo: Graduate School of Engineering, Nagoya University
Takuya Masuda: Global Research Center for Environment and Energy Based on Nanomaterials Science (GREEN), National Institute for Materials Science (NIMS)
Tomoaki Nishino: Graduate School of Science and Engineering, Tokyo Institute of Technology, Ookayama
Narendra P. Arasu: Institute of Physics, Academy of Sciences of the Czech Republic
Héctor Vázquez: Institute of Physics, Academy of Sciences of the Czech Republic
Manabu Kiguchi: Graduate School of Science and Engineering, Tokyo Institute of Technology, Ookayama

Nature Communications, 2017, vol. 8, issue 1, 1-8

Abstract: Abstract Aromaticity is a fundamental concept in chemistry. It is described by Hückel’s rule that states that a cyclic planar π-system is aromatic when it shares 4n+2 π-electrons and antiaromatic when it possesses 4n π-electrons. Antiaromatic compounds are predicted to exhibit remarkable charge transport properties and high redox activities. However, it has so far only been possible to measure compounds with reduced aromaticity but not antiaromatic species due to their energetic instability. Here, we address these issues by investigating the single-molecule charge transport properties of a genuinely antiaromatic compound, showing that antiaromaticity results in an order of magnitude increase in conductance compared with the aromatic counterpart. Single-molecule current–voltage measurements and ab initio transport calculations reveal that this results from a reduced energy gap and a frontier molecular resonance closer to the Fermi level in the antiaromatic species. The conductance of the antiaromatic complex is further modulated electrochemically, demonstrating its potential as a high-conductance transistor.

Date: 2017
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DOI: 10.1038/ncomms15984

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