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

doi:10.1021/jacs.7b07750

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

J Am Chem Soc. 2017 Oct 18;139(41):14356-14359. doi: 10.1021/jacs.7b07750. Epub 2017 Oct 4.

Authors

Brian J Eckstein¹, Ferdinand S Melkonyan¹, Eric F Manley^{1

2}, Simone Fabiano^{1

3}, Aidan R Mouat¹, Lin X Chen^{1

2}, Antonio Facchetti^{1

4}, Tobin J Marks^{1

5}

Affiliations

¹ 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.
² Chemical Sciences and Engineering Division, Argonne National Laboratory , 9700 South Cass Avenue, Lemont, Illinois 60439, United States.
³ Laboratory of Organic Electronics, Department of Science and Technology, Linköping University , Norrköping SE-60174, Sweden.
⁴ Flexterra Corporation , 8025 Lamon Avenue, Skokie, Illinois 60077, United States.
⁵ 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.

PMID: 28948782
DOI: 10.1021/jacs.7b07750

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 μ_e and μ_h of up to 0.39 and 0.32 cm²/(V·s), respectively.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, Non-U.S. Gov't