%0 Journal Article %T Novel electron-deficient oligo(phenyleneethynylene) derivatives for molecular electronics %+ Institut des Sciences Chimiques de Rennes (ISCR) %+ Université frères Mentouri Constantine I (UMC) %A Kitouni, R. %A Selvanathan, P. %A Galangau, Olivier %A Norel, L. %A Ouarda, B. %A Rigaut, S. %Z ANR-12-BS07-0010-01, ANR, Agence Nationale de la Recherche %Z MHEandSR, Ministry of Higher Education and Scientific Research %Z CNRS, Centre National de la Recherche Scientifique %< avec comité de lecture %@ 0039-7911 %J Synthetic Communications %I Taylor & Francis: STM, Behavioural Science and Public Health Titles %V 48 %N 9 %P 1052-1059 %8 2018 %D 2018 %R 10.1080/00397911.2018.1434205 %K Sonogashira coupling tetrafluorobenzene %K oligo(phenylethylene) %K molecular electronics %K Dinitrobenzene %Z Chemical SciencesJournal articles %X This work reports synthesis and characterizations of two new electron-poor “oligo(phenyleneethynylene) (OPE) type” molecular wires for fundamental studies of electron transport in molecular junctions. These OPE derivatives display three aromatic rings functionalized (i) with NO2 (OPN) or fluorine (OPF) groups on the central aryl core and (ii) with the requisite protected thiolate anchoring groups on the lateral rings at both ends. We show that the moderately effective Sonogashira couplings can give access to such rare electrodeficient molecules but are unfortunately associated with significant side reactions. We detail the choice of adequate reaction conditions to allow the recovery of suitable amounts of compounds bearing several strongly electron-withdrawing substituents on their central ring for further study of the physical properties. © 2018 Taylor and Francis. %G English %L hal-01809163 %U https://univ-rennes.hal.science/hal-01809163 %~ UNIV-RENNES1 %~ CNRS %~ INSA-RENNES %~ ENSC-RENNES %~ ISCR %~ SCR_OMC2012 %~ ISCR-OMC %~ STATS-UR1 %~ UR1-SPM %~ INC-CNRS %~ UR1-UFR-SPM %~ UR1-HAL %~ UR1-SDLM %~ TEST-UR-CSS %~ UNIV-RENNES %~ INSA-GROUPE %~ TEST-HALCNRS %~ ANR %~ UR1-MMS %~ TEST2-HALCNRS