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The Synthesis of Functionalised Diaryltetraynes and Their Transport Properties in Single‐Molecule Junctions
Author(s) -
Gulcur Murat,
MorenoGarcía Pavel,
Zhao Xiaotao,
Baghernejad Masoud,
Batsanov Andrei S.,
Hong Wenjing,
Bryce Martin R.,
Wandlowski Thomas
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304671
Subject(s) - molecule , conductance , chemistry , break junction , decomposition , quantum tunnelling , derivative (finance) , crystallography , stereochemistry , materials science , optoelectronics , physics , organic chemistry , financial economics , economics , condensed matter physics
The synthesis and characterisation is described of six diaryltetrayne derivatives [Ar‐(CC) 4 ‐Ar] with Ar=4‐NO 2 ‐C 6 H 4 ‐ ( NO 2 4 ), 4‐NH(Me)C 6 H 4 ‐ ( NHMe4 ), 4‐NMe 2 C 6 H 4 ‐ ( NMe 2 4 ), 4‐NH 2 ‐(2,6‐dimethyl)C 6 H 4 ‐ ( DMeNH 2 4 ), 5‐indolyl ( IN4 ) and 5‐benzothienyl ( BTh4 ). X‐ray molecular structures are reported for NO 2 4 , NHMe4 , DMeNH 2 4 , IN4 and BTh4 . The stability of the tetraynes has been assessed under ambient laboratory conditions (20 °C, daylight and in air): NO 2 4 and BTh4 are stable for at least six months without observable decomposition, whereas NHMe4 , NMe 2 4 , DMeNH 2 4 and IN4 decompose within a few hours or days. The derivative DMeNH 2 4 , with ortho ‐methyl groups partially shielding the tetrayne backbone, is considerably more stable than the parent compound with Ar=4‐NH 2 C 6 H 4 ( NH 2 4 ). 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.