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dc.contributor.authorÖzdemir, Resul
dc.contributor.authorPark, Sangyun
dc.contributor.authorDeneme, İbrahim
dc.contributor.authorPark, Yonghan
dc.contributor.authorZorlu, Yunus
dc.contributor.authorArdic Alidağı, Hüsniye
dc.contributor.authorHarmandar, Kevser
dc.contributor.authorKim, Choongik
dc.contributor.authorUsta, Hakan
dc.date.accessioned2019-06-25T07:59:39Z
dc.date.available2019-06-25T07:59:39Z
dc.date.issued2018en_US
dc.identifier.citationOrg. Chem. Front., 2018,5, 2912-2924en_US
dc.identifier.otherDOI:10.1039/C8QO00856F
dc.identifier.urihttp://acikerisim.agu.edu.tr/xmlui/handle/20.500.12573/16
dc.description.abstractThe design and synthesis of novel electron-deficient and solution-processable polycyclic aromatic hydrocarbons offers great opportunities for the development of low-cost and large-area (opto)electronics. Although (trialkylsilyl)ethynyl (R3Si–C C–) has emerged as a very popular unit to solubilize organic semiconductors, it has been applied only to a limited class of materials that are mostly substituted on short molecular axes. Herein, two novel solution-processable indenofluorenebased semiconductors, TIPS-IFDK and TIPS-IFDM, bearing (triisopropylsilyl)ethynyl end units at 2,8-positions (long molecular axis substitution) were synthesized, and their single-crystal structures, optoelectronic properties, solution-sheared thin-film morphologies/microstructures, and n-channel field-effect responses were studied. In accordance with the DFT calculations, the HOMO/LUMO energies of the new compounds are found to be -5.77/-3.65 eV and -5.84/-4.18 eV for TIPS-IFDK and TIPS-IFDM, respectively, reflecting the high electron deficiency of the new ?-backbones. Both semiconductors exhibit slightly S-shaped molecular frameworks with highly coplanar IFDK/IFDM ?-cores, and they form slipped ?-stacked one-dimensional (1-D) columnar motifs in the solid state. However, substantial differences in the degree of ?–? interactions and stacking distances (4.04 Å vs. 3.47 Å) were observed between TIPS-IFDK and TIPS-IFDM as a result of carbonyl vs. dicyanovinylene functionalization, which results in a three orders of magnitude variation in the charge carrier mobility of the corresponding thin films. Top-contact/bottom-gate OFETs fabricated via solution-shearing TIPS-IFDM yielded one of the best performances in the (trialkylsilyl)ethynyl literature (µe = 0.02 cm2 V-1 s -1 , Ion/Ioff = 107–108 , and VT ~ 2 V under ambient atmosphere) for a 1-D polycrystalline semiconductor microstructure. To the best of our knowledge, the molecules presented here are the first examples of n-type semiconductors substituted with (trialkylsilyl)ethynyl groups on their long molecular axes.en_US
dc.language.isoengen_US
dc.publisherRoyal Society of Chemistryen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.titleTriisopropylsilylethynyl-substituted indenofluorenes: carbonyl versus dicyanovinylene functionalization in one-dimensional molecular crystals and solution-processed n-channel OFETsen_US
dc.typearticleen_US
dc.contributor.departmentAGÜ, Mühendislik Fakültesi, Malzeme Bilimi ve Nanoteknoloji Mühendisliği Bölümüen_US
dc.contributor.institutionauthor
dc.identifier.doi10.1039/C8QO00856F
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US


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