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Helical thienothiophene (TT) and benzothieno–benzothiophene (BTBT) derivatives: synthesis, structural characterization and semiconducting properties

dc.rights.licenseopenen_US
dc.contributor.authorTALAMO, Maurizio Mastropasqua
dc.contributor.authorPOP, Flavia
dc.contributor.authorHUME, Paul
hal.structure.identifierLaboratoire de l'intégration, du matériau au système [IMS]
dc.contributor.authorABBAS, Mamatimin
hal.structure.identifierLaboratoire de l'intégration, du matériau au système [IMS]
dc.contributor.authorWANTZ, Guillaume
dc.contributor.authorAVARVARI, Narcis
dc.date.accessioned2022-08-26T08:30:10Z
dc.date.available2022-08-26T08:30:10Z
dc.date.issued2022-01-01
dc.identifier.issn2050-7526en_US
dc.identifier.otherhttps://www.rsc.org/suppdata/d2/tc/d2tc00861k/d2tc00861k1.pdfen_US
dc.identifier.urioai:crossref.org:10.1039/d2tc00861k
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/140591
dc.description.abstractEnThienothiophene (TT) and benzothieno–benzothiophene (BTBT) have been successfully included here in the helical backbone of helicene derivatives. The employed synthetic approach gives access in a controlled manner to both simple and double helicenic structures decorated with side alkyl chains to provide solubility. Whereas in the solid state structure the M and P forms of the mono-helicene stack in alternating rows of each enantiomer and show segregation between the aromatic and aliphatic parts, the crystal of the bis-helicene is formed of homochiral sheets of MM and PP enantiomers. These helical TT and BTBT materials have been tested as racemic mixtures in organic field-effect transistor (OFET) devices fabricated by both spin coating and vapour deposition. The bis-helicene derivative, in which crystal packing is dominated by π–π stacking interactions, behaves as a p-type semiconductor with a hole mobility of 3.5 × 10−5 cm2 V−1 s−1 in close agreement with the predicted value by DFT calculations. The OFETs of mono-helicene do not show charge transport despite the superior predicted mobility based on the crystal structure, suggesting that amorphous films suffer from a broader distribution of hole energies, which limits the number of thermally accessible hopping pathways. The benefits of embedding TT and BTBT units into helicenic structures in terms of synthetic strategy, structural variation and mobility pave the way for chiral semiconducting BTBT helicenes.
dc.language.isoENen_US
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dc.title.enHelical thienothiophene (TT) and benzothieno–benzothiophene (BTBT) derivatives: synthesis, structural characterization and semiconducting properties
dc.typeArticle de revueen_US
dc.identifier.doi10.1039/d2tc00861ken_US
dc.subject.halChimie/Matériauxen_US
bordeaux.journalJournal of Materials Chemistry Cen_US
bordeaux.page8034-8042en_US
bordeaux.volume10en_US
bordeaux.hal.laboratoriesLaboratoire d’Intégration du Matériau au Système (IMS) - UMR 5218en_US
bordeaux.issue20en_US
bordeaux.institutionUniversité de Bordeauxen_US
bordeaux.institutionBordeaux INPen_US
bordeaux.institutionCNRSen_US
bordeaux.peerReviewedouien_US
bordeaux.inpressnonen_US
bordeaux.import.sourcedissemin
hal.identifierhal-03761442
hal.version1
hal.date.transferred2022-08-26T08:30:12Z
hal.exporttrue
workflow.import.sourcedissemin
dc.rights.ccPas de Licence CCen_US
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Journal%20of%20Materials%20Chemistry%20C&rft.date=2022-01-01&rft.volume=10&rft.issue=20&rft.spage=8034-8042&rft.epage=8034-8042&rft.eissn=2050-7526&rft.issn=2050-7526&rft.au=TALAMO,%20Maurizio%20Mastropasqua&POP,%20Flavia&HUME,%20Paul&ABBAS,%20Mamatimin&WANTZ,%20Guillaume&rft.genre=article


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