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The synthesis and characterisation is described of six diaryltetrayne derivatives [Ar-(C?C)4-Ar] with Ar=4-NO2-C 6H4- (NO24), 4-NH(Me)C6H 4- (NHMe4), 4-NMe2C6H4- (NMe 24), 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. Lay anchor: Oligoynes with a range of terminal functional groups, for example, benzo[b]thiophene (BTh4; see figure) have been synthesised. The charge transport characteristics of oligoynes in single-molecular junctions anchored between gold electrodes were studied. With careful choice of the anchor group oligoynes are shown to be a viable family of stable molecular wires for molecular-electronics applications.
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Reference:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem