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In-Situ Formation of H-Bonding Imidazole Chains in Break-Junction Experiments

preprint
submitted on 14.10.2019 and posted on 21.10.2019 by Chuanli Wu, Aminah Alqahtani, Sara Sangtarash, Andrea Vezzoli, Hatef Sadeghi, Craig M. Robertson, Chenxin Cai, Colin Lambert, Simon Higgins, Richard Nichols
As a small molecule possessing both strong H-bond donor and acceptor functions, 1H-imidazole can participate in extensive homo- or heteromolecular H-bonding networks. These properties are important in Nature, as imidazole moieties are incorporated in many biologically-relevant compounds. Imidazole also finds applications ranging from corrosion inhibition to fire retardants and photography. We have found a peculiar behaviour of imidazole during scanning tunnelling microscopy-break junction (STM-BJ) experiments, in which oligomeric chains connect the two electrodes and allow efficient charge transport. We attributed this behaviour to the formation of hydrogen-bonding networks, as no evidence of such behaviour was found in 1-methylimidazole (incapable of participating in intramolecular hydrogen bonding). The results are supported by DFT calculations, which confirmed our hypothesis. These findings pave the road to the use of hydrogen-bonding networks for the fabrication of dynamic junctions based on supramolecular interactions.

Funding

EPSRC EP/M005046/1

EPSRC EP/M029522/1

EPSRC EP/M014452/1

EPSRC EP/M014169/1

EPSRC EP/P027156/1

EPSRC EP/N03337X/1

FET Open Project 767187 QuIET

Leverhulme Early Career Fellowship ECF-2018-375

UKRI Future Leaders Fellowship MR/S015329/1

China Scholarship Council 201806860023

History

Email Address of Submitting Author

andrea.vezzoli@liverpool.ac.uk

Institution

University of Liverpool

Country

United Kingdom

ORCID For Submitting Author

0000-0002-8059-0113

Declaration of Conflict of Interest

No conflict of interest

Version Notes

1.1 - Added TOC & correction to SI

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