ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
3 files

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

preprint
submitted on 14.10.2019, 14:18 and posted on 21.10.2019, 16:27 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

Exports