Naphthalene Bis(4,8-diamino-1,5-dicarboxyl)amide Building Block for Semiconducting Polymers

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]
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.

Melkonyan, Ferdinand S.Northwestern University, IL 60208 USA (författare)
Manley, Eric F.Northwestern University, IL 60208 USA; Argonne National Lab, IL 60439 USA (författare)
Fabiano, SimoneLinköpings universitet,Fysik och elektroteknik,Tekniska fakulteten,Northwestern University, IL 60208 USA(Swepub:liu)simfa84 (författare)
Moua, Aidan R.Northwestern University, IL 60208 USA (författare)
Chen, Lin X.Northwestern University, IL 60208 USA; Argonne National Lab, IL 60439 USA (författare)
Facchetti, AntonioNorthwestern University, IL 60208 USA; Flexterra Corp, IL 60077 USA (författare)
Marks, Tobin J.Northwestern University, IL 60208 USA (författare)
Northwestern University, IL 60208 USANorthwestern University, IL 60208 USA; Argonne National Lab, IL 60439 USA (creator_code:org_t)

Ingår i:Journal of the American Chemical Society: AMER CHEMICAL SOC139:41, s. 14356-143590002-78631520-5126

Av författaren/redakt...: Eckstein, Brian ...; Melkonyan, Ferdi ...; Manley, Eric F.; Fabiano, Simone; Moua, Aidan R.; Chen, Lin X.; visa fler...; Facchetti, Anton ...; Marks, Tobin J.; visa färre...

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