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

Brian J. Eckstein, Ferdinand S. Melkonyan*, Eric F. Manley, Simone Fabiano, Aidan R. Mouat, Lin X. Chen, Antonio Facchetti, Tobin J. Marks

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

43 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)14356-14359
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number41
DOIs
StatePublished - Oct 18 2017

Funding

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.

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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