Naphthalene Bis(4,8-diamino-1,5-dicarboxyl)amide Building Block for Semiconducting Polymers.
We report a new naphthalene bis(4,8-diamino-1,5-dicarboxyl)amide (NBA) building block for polymeric semiconductors. Computational modeling suggests that regio-connectivity at the 2,6- or 3,7-NBA positions strongly modulates polymer backbone torsion and, therefore, intramolecular π-conjugation and ag...
| Publicado en: | Journal of the American Chemical Society Vol. 139; no. 41; pp. 14356 - 14360 |
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| Autores principales: | , , , , , , , |
| Formato: | Artículo |
| Publicado: |
American Chemical Society
10/18/2017
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| Materias: | |
| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=hlh&AN=125891785&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 125891785 longDbName: Humanities International Complete uiTag: AN controlInfo: bkinfo: jinfo: jid: 00027863 ACS jtl: Journal of the American Chemical Society issn: 00027863 maglogo: N pubinfo: dt: 10/18/2017 vid: 139 iid: 41 pid: 997 pub: American Chemical Society artinfo: ui: 125891785 10.1021/jacs.7b07750 ppf: 14356 ppct: 4 formats: tig: atl: Naphthalene Bis(4,8-diamino-1,5-dicarboxyl)amide Building Block for Semiconducting Polymers. aug: au: Eckstein, Brian J. Melkonyan, Ferdinand S. Manley, Eric F. Fabiano, Simone Mouat, Aidan R. Chen, Lin X. Facchetti, Antonio Marks, Tobin J. affil: Department of Chemistry and the Materials Research Center, and the Argonne-Northwestern Solar Energy Research Center, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States Chemical Sciences and Engineering Division, Argonne National Laboratory, 9700 South Cass Avenue, Lemont, Illinois 60439, United States Laboratory of Organic Electronics, Department of Science and Technology, Linköping University, Norrköping SE-60174, Sweden Flexterra Corporation, 8025 Lamon Avenue, Skokie, Illinois 60077, United States Department of Materials Science and Engineering and the Materials Research Center, and the Argonne-Northwestern Solar Energy Research Center, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States su: Naphthalene Naphthyl compounds Organic semiconductors X-ray diffraction Polymers sug: subj: Naphthalene Naphthyl compounds Organic semiconductors X-ray diffraction Polymers ab: We report a new naphthalene bis(4,8-diamino-1,5-dicarboxyl)amide (NBA) building block for polymeric semiconductors. Computational modeling suggests that regio-connectivity at the 2,6- or 3,7-NBA positions strongly modulates polymer backbone torsion and, therefore, intramolecular π-conjugation and aggregation. Optical, electrochemical, and X-ray diffraction characterization of 3,7- and 2,6-dithienyl-substituted NBA molecules and corresponding isomeric NBAbithiophene copolymers P1 and P2, respectively, reveals the key role of regio-connectivity. Charge transport measurements demonstrate that while the twisted 3,7- NDA-based P1 is a poor semiconductor, the planar 2,6- functionalized NBA polymers (P2-P4) exhibit ambipolarity, with μe and μh of up to 0.39 and 0.32 cm2/(V·s), respectively. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2017 holdings: @attributes: islocal: N |
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