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Exploring antiaromaticity in single-molecule junctions formed from biphenylene derivatives

Gantenbein, Markus; Li, Xiaohui; Sangtarash, Sara; Bai, Jie; Olsen, Gunnar; Alqorashi, Afaf; Hong, Wenjing; Lambert, Colin J.; Bryce, Martin R.

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Authors

Markus Gantenbein

Xiaohui Li

Sara Sangtarash

Jie Bai

Gunnar Olsen

Afaf Alqorashi

Wenjing Hong

Colin J. Lambert



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.

Citation

Gantenbein, M., Li, X., Sangtarash, S., Bai, J., Olsen, G., Alqorashi, A., …Bryce, M. R. (2019). Exploring antiaromaticity in single-molecule junctions formed from biphenylene derivatives. Nanoscale, 11(43), 20659-20666. https://doi.org/10.1039/c9nr05375a

Journal Article Type Article
Acceptance Date Aug 26, 2019
Online Publication Date Oct 23, 2019
Publication Date Nov 21, 2019
Deposit Date Oct 23, 2019
Publicly Available Date Oct 23, 2019
Journal Nanoscale
Print ISSN 2040-3364
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 11
Issue 43
Pages 20659-20666
DOI https://doi.org/10.1039/c9nr05375a

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