A one-pot synthesis of oligo(arylene–ethynylene)-molecular wires and their use in the further verification of molecular circuit laws

A convenient two-step, one-pot synthesis of oligo(arylene–ethynylene) (OAE) type molecular wires in yields up to 70% via situ desilylation protected bis(alkynes) Me3SiC?CArC?CSiMe3 (Ar = 2,5-thienyl, 1,4-naphthylene, 9,10-anthrylene) and subsequent Sonogashira cross-coupling with S-(4-iodophenyl) ethanethiolate, 4-iodothioanisole, or 5-bromo-3,3-dimethyl-2,3-dihydrobenzo[b]thiophene is described. The avoids the manipulation sensitive terminal dialkynes (HC?CArC?CH), whilst general approach presented has some advantages over alternative synthetic strategies based on coupling aryl dihalides (XArX) by avoiding multi-step preparation purification alkynes S-(4-ethynylphenyl) 4-ethynylthioanisole 5-ethynyl 3,3-dimethyl-2,3-dihydrobenzo[b]thiophene. conductance resulting thiolate thioether functionalised OAE been determined using scanning tunneling microscope break junction (STM-BJ) methods. trends do not track simply degree aromaticity core despite rather similar lengths. Rather, STM-BJ data are better correlated nature anchor group, highlighting important role electrode–molecule electron transport a junction. experimental good agreement recently described quantum circuit rules, further potential for these relationships be used as predictive tools electronics research.