%0 Journal Article %T Electron deficient dicyanovinylene-ladder-type pentaphenylene derivative for n-type Organic Field Effect Transistors %+ Institut d'Électronique et des Technologies du numéRique (IETR) %+ Institut des Sciences Chimiques de Rennes (ISCR) %A Jacques, Emmanuel %A Romain, Maxime %A Yassin, Ali %A Bebiche, Sarah %A Harnois, Maxime %A Mohammed-Brahim, Tayeb %A Rault-Berthelot, Joëlle %A Poriel, Cyril %< avec comité de lecture %@ 2050-7526 %J Journal of Materials Chemistry C %I Royal Society of Chemistry %V 2 %N 17 %P 3292-3302 %8 2014 %D 2014 %R 10.1039/C3TC31925C %Z Chemical Sciences/Material chemistryJournal articles %X A bridged pentaphenylene derivative functionalized with dicyanovinylene units LPP([double bond, length as m-dash]C(CN)2)2 has been designed, synthesized and characterized. The optical and electrochemical properties have been carefully studied through a combined experimental and theoretical approach and compared with those of two pentaphenylene derivatives bearing methylenes (LPP) or carbonyl (LPP([double bond, length as m-dash]O)2) on the bridgeheads. LPP([double bond, length as m-dash]C(CN)2)2 which possesses a very low LUMO level, ca. −4.02 eV, has been successfully used as an active layer in n-channel OFETs using the epoxy based photoresist SU-8 as a gate insulator. LPP([double bond, length as m-dash]C(CN)2)2 based n-channel OFETs show low voltage functioning (low gate-source and drain-source voltages), high ratio between the on and the off currents (2 × 105), interesting subthreshold swing (S = 1) and excellent stability under electrical stress and in a nitrogen atmosphere. More importantly, we have also shown that LPP([double bond, length as m-dash]C(CN)2)2 based n-channel OFETs present an excellent environmental stability. This work is to the best of our knowledge the first report on bridged pentaphenylene-based semiconductors in n-type OFETs and highlights the potential of such type of material to provide air stable OFETs. %G English %2 https://univ-rennes.hal.science/hal-01066947/document %2 https://univ-rennes.hal.science/hal-01066947/file/Electron_deficient_dicyanovinylene-ladder-type_accepted.pdf %L hal-01066947 %U https://univ-rennes.hal.science/hal-01066947 %~ UNIV-NANTES %~ UNIV-RENNES1 %~ CNRS %~ INSA-RENNES %~ ENSC-RENNES %~ IETR %~ ISCR %~ SCR_MACSE %~ IETR_DE %~ SCR_CTI %~ STATS-UR1 %~ UR1-SPM %~ INC-CNRS %~ UR1-UFR-SPM %~ UR1-HAL %~ UR1-MATH-STIC %~ UR1-SDLM %~ UR1-UFR-ISTIC %~ IETR-MM %~ TEST-UNIV-RENNES %~ TEST-UR-CSS %~ UNIV-RENNES %~ INSA-GROUPE %~ UR1-MATH-NUM %~ UR1-MMS %~ NANTES-UNIVERSITE %~ UNIV-NANTES-AV2022 %~ TEST2-HALCNRS