Jump to main content
Jump to site search

Issue 43, 2019
Previous Article Next Article

Exploring antiaromaticity in single-molecule junctions formed from biphenylene derivatives

Author affiliations

Abstract

We report the synthesis of a series of oligophenylene-ethynylene (OPE) derivatives with biphenylene core units, designed to assess the effects of biphenylene antiaromaticity on charge transport in molecular junctions. Analogues with naphthalene, anthracene, fluorene and biphenyl cores are studied for comparison. The molecules are terminated with pyridyl or methylthio units. Single-molecule conductance data were obtained using the mechanically controllable break junction (MCBJ) technique. It is found that when electrons pass from one electrode to the other via a phenylene ring, the electrical conductance is almost independent of the nature of the pendant π-systems attached to the phenylene ring and is rather insensitive to antiaromaticity. When electrons pass through the cyclobutadiene core of the biphenylene unit, transport is sensitive to the presence of the relatively weak single bonds connecting the two phenylene rings of biphenylene, which arise from partial antiaromaticity within the cyclobutadiene core. This leads to a negligible difference in the molecular conductance compared to the fluorene or biphenyl analogues which have standard single bonds. This ability to tune the conductance of molecular cores has no analogue in junctions formed from artificial quantum dots and reflects the quantum nature of electron transport in molecular junctions, even at room temperature.

Graphical abstract: Exploring antiaromaticity in single-molecule junctions formed from biphenylene derivatives

Back to tab navigation

Supplementary files

Publication details

The article was received on 25 Jun 2019, accepted on 26 Aug 2019 and first published on 23 Oct 2019


Article type: Paper
DOI: 10.1039/C9NR05375A
Nanoscale, 2019,11, 20659-20666
  • Open access: Creative Commons BY license
  •   Request permissions

    Exploring antiaromaticity in single-molecule junctions formed from biphenylene derivatives

    M. Gantenbein, X. Li, S. Sangtarash, J. Bai, G. Olsen, A. Alqorashi, W. Hong, C. J. Lambert and M. R. Bryce, Nanoscale, 2019, 11, 20659
    DOI: 10.1039/C9NR05375A

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements