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Naphthalene Bis(4,8-diamino-1,5-dicarboxyl)amide Building Block for Semiconducting Polymers
Northwestern University, IL 60208 USA.
Northwestern University, IL 60208 USA.
Northwestern University, IL 60208 USA; Argonne National Lab, IL 60439 USA.
Linköping University, Department of Science and Technology, Physics and Electronics. Linköping University, Faculty of Science & Engineering. Northwestern University, IL 60208 USA.ORCID iD: 0000-0001-7016-6514
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2017 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 139, no 41, 14356-14359 p.Article in journal (Refereed) Published
Abstract [en]

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 pi-conjugation and aggregation. Optical, electrochemical, and X-ray diffraction characterization of 3,7- and 2,6-dithienyl-substituted NBA molecules and, corresponding isomeric NBA, bithiophene 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 mu(e) and mu(h) of up to 0.39 and 0.32 cm(2)/(V.s), respectively.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC , 2017. Vol. 139, no 41, 14356-14359 p.
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Condensed Matter Physics
Identifiers
URN: urn:nbn:se:liu:diva-142985DOI: 10.1021/jacs.7b07750ISI: 000413503300007PubMedID: 28948782OAI: oai:DiVA.org:liu-142985DiVA: diva2:1156541
Note

Funding Agencies|Argonne-Northwestern Solar Energy Research (ANSER) Center; Energy Frontier Research Center - U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences [DE-SC0001059]; AFOSR [FA9550-15-1-0044]; U.S. Department of Commerce [70NANB14H012]; Qatar NPRP [7-286-1-046]; U.S. Department of Commerce, National Institute of Standards and Technology, as part of the Center for Hierarchical Materials Design (CHiMaD) [70NANB14H012]; Shenzhen Peacock Plan project [KQTD20140630110339343]; VINNOVA [2015-04859]; Swedish Research Council [2016-03979]

Available from: 2017-11-13 Created: 2017-11-13 Last updated: 2017-11-13

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