TY - JOUR
T1 - Naphthalene Bis(4,8-diamino-1,5-dicarboxyl)amide Building Block for Semiconducting Polymers
AU - Eckstein, Brian J.
AU - Melkonyan, Ferdinand S.
AU - Manley, Eric F.
AU - Fabiano, Simone
AU - Mouat, Aidan R.
AU - Chen, Lin X.
AU - Facchetti, Antonio
AU - Marks, Tobin J.
N1 - Funding Information:
This research was supported in part by Argonne-Northwestern Solar Energy Research (ANSER) Center, an Energy Frontier Research Center funded by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences, under Award Number DE-SC0001059 (B.J.E., polymer synthesis), and by AFOSR grant FA9550-15-1-0044 (A.F., synthetic design). F.S.M. was supported by award 70NANB14H012 from U.S. Department of Commerce, and E.F.M. by Qatar NPRP grant 7-286-1-046. This work was performed with financial assistance under award 70NANB14H012 from the U.S. Department of Commerce, National Institute of Standards and Technology, as part of the Center for Hierarchical Materials Design (CHiMaD). A.F. thanks the Shenzhen Peacock Plan project (KQTD20140630110339343) for financial support. S.F. thanks VINNOVA (2015-04859) and the Swedish Research Council (2016-03979) for financial support.
PY - 2017/10/18
Y1 - 2017/10/18
N2 - 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 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 μe and μh of up to 0.39 and 0.32 cm2/(V·s), respectively.
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 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 μe and μh of up to 0.39 and 0.32 cm2/(V·s), respectively.
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U2 - 10.1021/jacs.7b07750
DO - 10.1021/jacs.7b07750
M3 - Article
C2 - 28948782
AN - SCOPUS:85031758979
VL - 139
SP - 14356
EP - 14359
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 41
ER -