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dc.contributor.authorOzdemir, Resul
dc.contributor.authorAhn, Kyunghan
dc.contributor.authorDeneme, Ibrahim
dc.contributor.authorZorlu, Yunus
dc.contributor.authorKim, Dojun
dc.contributor.authorKim, Myung-Gil
dc.contributor.authorUsta, Hakan
dc.date.accessioned2021-01-25T09:01:28Z
dc.date.available2021-01-25T09:01:28Z
dc.date.issued2020en_US
dc.identifier.issn2050-7526
dc.identifier.issn2050-7534
dc.identifier.urihttps://doi.org/10.1039/d0tc02945a
dc.identifier.urihttps://hdl.handle.net/20.500.12573/473
dc.descriptionH. U., R. O., and I. D. acknowledge support from the Scientific and Technological Research Council of Turkey (TUBITAK) grant number 216M430. M.-G. K. and K. A. acknowledge support from the National Research Foundation of Korea (NRF) grant number 2016K2A9A1A06924256. We thank Prof. E. Mutlugun and A. F. Yazici for their help with the photoluminescence measurements.en_US
dc.description.abstractDiacene-fused thienothiophenes (DAcTTs) have provided an excellent pi-framework for the development of high mobility p-type molecular semiconductors in the past decade. However, n-type DAcTTs are rare and their electron transport characteristics remain largely unexplored. Herein, a series of functionalized low LUMO (lowest unoccupied molecular orbital) [1]benzothieno[3,2-b][1]benzothiophene (BTBT)-based small molecules, D(C7CO)-BTBT, C7CO-BTBT-CC(CN)(2)C-7, and D(C7CC(CN)(2))-BTBT, have been developed. Detailed structural, physicochemical, optoelectronic, and single-crystal characterization were performed. The new molecules exhibit large optical band gaps (similar to 2.8-3.1 eV) and highly stabilized (-Delta E-LUMO = 1.2-1.4 eV)/pi-delocalized LUMOs as compared to p-type DAcTTs. Symmetric functionalization is found to be important to enable strong intermolecular interactions in the solid-state. All molecules exhibit alternately stacked layers of "F-BTBT-F" and "S" (F: functional group/S: substituent) with strong herringbone-like interactions (2.8-3.6 angstrom distances) between pi-cores. While carbonyls, regardless of the substituent, adopt nearly coplanar pi-backbones with BTBT, dicyanovinylenes are found to be twisted (47.5 degrees). The conformational difference at the molecular level has unusual effects on the pi-electron deficiencies, frontier molecular orbital energetics, thermal/photophysical properties, and pi-electronic structures. Dicyanovinylenes at the 2,7 positions, despite twisted conformations, are shown for the first time to yield good electron transport in DAcTTs. The D(C7CC(CN)(2))-BTBT thin film exhibits large 2D plate-like crystalline grains (similar to 1-2 mu m sizes) of terraced islands and becomes a rare example of an n-type DAcTT in organic field-effect transistors (OFETs). Although a stabilized/pi-delocalized LUMO, largely governed by functional groups and intramolecular twists, is essential for electron transport, our findings suggest that it should be combined with proper substituents to yield a favorable three-dimensional BTBT/functional group pi-electronic structure and a low intramolecular reorganization energy. Combined with our first n-type DAcTT semiconductor D(PhFCO)-BTBT, a molecular library with systematically varied chemical structures has been studied herein for the first time for low LUMO DAcTTs. The molecular engineering perspectives presented in this study may give unique insights into the design of novel electron transporting thienoacenes for unconventional optoelectronics.en_US
dc.description.sponsorshipTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) 216M430 National Research Foundation of Korea 2016K2A9A1A06924256en_US
dc.language.isoengen_US
dc.publisherROYAL SOC CHEMISTRY, THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLANDen_US
dc.relation.isversionof10.1039/d0tc02945aen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectFIELD-EFFECT TRANSISTORSen_US
dc.subjectTHIN-FILM TRANSISTORSen_US
dc.subjectHIGH-ELECTRON-MOBILITYen_US
dc.subjectN-TYPEen_US
dc.subjectHIGH-PERFORMANCEen_US
dc.subjectORGANIC SEMICONDUCTORSen_US
dc.subjectDESIGN STRATEGIESen_US
dc.subjectQUANTUM DOTSen_US
dc.subjectOLIGOMERSen_US
dc.subjectTURN-ONen_US
dc.titleEngineering functionalized low LUMO [1]benzothieno[3,2-b][1]benzothiophenes (BTBTs): unusual molecular and charge transport propertiesen_US
dc.typearticleen_US
dc.contributor.departmentAGÜ, Mühendislik Fakültesi, Malzeme Bilimi ve Nanoteknoloji Mühendisliği Bölümüen_US
dc.contributor.authorID0000-0002-7957-110Xen_US
dc.identifier.volumeVolume: 8en_US
dc.identifier.issue43en_US
dc.identifier.startpage15253en_US
dc.identifier.endpage15267en_US
dc.relation.journalJOURNAL OF MATERIALS CHEMISTRY Cen_US
dc.relation.tubitak216M430
dc.relation.publicationcategoryMakale - Uluslararası - Editör Denetimli Dergien_US


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