The Synthesis of Functionalised Diaryltetraynes and Their Transport Properties in Single-Molecule Junctions

Gulcur, Murat; Moreno, Pavel; Zhao, Xiaotao; Baghernejad, Masoud; Batsanov, Andrei S.; Hong, Wenjing; Bryce, Martin R.; Wandlowski, Thomas (2014). The Synthesis of Functionalised Diaryltetraynes and Their Transport Properties in Single-Molecule Junctions. Chemistry - a European journal, 20(16), pp. 4653-4660. Wiley-VCH 10.1002/chem.201304671

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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.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry
10 Strategic Research Centers > Center for Space and Habitability (CSH)

UniBE Contributor:

Moreno, Pavel; Baghernejad, Masoud; Hong, Wenjing and Wandlowski, Thomas

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry
500 Science
500 Science > 520 Astronomy

ISSN:

0947-6539

Publisher:

Wiley-VCH

Language:

English

Submitter:

Beatrice Niederhauser

Date Deposited:

26 Mar 2015 10:55

Last Modified:

27 Mar 2015 02:21

Publisher DOI:

10.1002/chem.201304671

BORIS DOI:

10.7892/boris.65947

URI:

https://boris.unibe.ch/id/eprint/65947

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