M. Gulcur
The Synthesis of Functionalised Diaryltetraynes and Their Transport Properties in Single-Molecule Junctions
Gulcur, M.; Moreno-García, P.; Zhao, X.; Baghernejad, M.; Batsanov, A.S.; Hong, W.; Bryce, M.R.; Wandlowski, T.
Authors
P. Moreno-García
X. Zhao
M. Baghernejad
A.S. Batsanov
W. Hong
Professor Martin Bryce m.r.bryce@durham.ac.uk
Professor
T. Wandlowski
Abstract
The synthesis and characterisation is described of six diaryltetrayne derivatives [Ar-(C[TRIPLE BOND]C)4-Ar] with Ar=4-NO2-C6H4- (NO24), 4-NH(Me)C6H4- (NHMe4), 4-NMe2C6H4- (NMe24), 4-NH2-(2,6-dimethyl)C6H4- (DMeNH24), 5-indolyl (IN4) and 5-benzothienyl (BTh4). X-ray molecular structures are reported for NO24, NHMe4, DMeNH24, IN4 and BTh4. The stability of the tetraynes has been assessed under ambient laboratory conditions (20 °C, daylight and in air): NO24 and BTh4 are stable for at least six months without observable decomposition, whereas NHMe4, NMe24, DMeNH24 and IN4 decompose within a few hours or days. The derivative DMeNH24, with ortho-methyl groups partially shielding the tetrayne backbone, is considerably more stable than the parent compound with Ar=4-NH2C6H4 (NH24). The ability of the stable tetraynes to anchor in Au|molecule|Au junctions is reported. Scanning-tunnelling-microscopy break junction (STM-BJ) and mechanically controllable break junction (MCBJ) techniques are employed to investigate single-molecule conductance characteristics.
Citation
Gulcur, M., Moreno-García, P., Zhao, X., Baghernejad, M., Batsanov, A., Hong, W., …Wandlowski, T. (2014). The Synthesis of Functionalised Diaryltetraynes and Their Transport Properties in Single-Molecule Junctions. Chemistry - A European Journal, 20(16), 4653-4660. https://doi.org/10.1002/chem.201304671
| Journal Article Type | Article |
|---|---|
| Publication Date | Apr 1, 2014 |
| Deposit Date | Nov 24, 2014 |
| Publicly Available Date | Nov 26, 2014 |
| Journal | Chemistry - A European Journal |
| Print ISSN | 0947-6539 |
| Electronic ISSN | 1521-3765 |
| Publisher | Wiley |
| Peer Reviewed | Peer Reviewed |
| Volume | 20 |
| Issue | 16 |
| Pages | 4653-4660 |
| DOI | https://doi.org/10.1002/chem.201304671 |
| Keywords | Cross-coupling, Oligoynes, Polyynes, Single-molecule conductance, X-ray diffraction. |
| Public URL | https://durham-repository.worktribe.com/output/1419470 |
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Copyright Statement
This is the peer reviewed version of the following article: Gulcur, M., Moreno-García, P., Zhao, X., Baghernejad, M., Batsanov, A. S., Hong, W., Bryce, M. R. and Wandlowski, T. (2014), The Synthesis of Functionalised Diaryltetraynes and Their Transport Properties in Single-Molecule Junctions. Chemistry - A European Journal, 20 (16): 4653-4660, which has been published in final form at http://dx.doi.org/10.1002/chem.201304671. This article may be used for non-commercial purposes in accordance With Wiley-VCH Terms and Conditions for self-archiving.