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

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

Northwestern University

Research output: Contribution to journal › Article

16 Citations (Scopus)

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.

Original language	English
Pages (from-to)	14356-14359
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	41
DOIs	https://doi.org/10.1021/jacs.7b07750
Publication status	Published - Oct 18 2017

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ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Cite this

Eckstein, B. J., Melkonyan, F. S., Manley, E. F., Fabiano, S., Mouat, A. R., Chen, L. X., Facchetti, A., & Marks, T. J. (2017). Naphthalene Bis(4,8-diamino-1,5-dicarboxyl)amide Building Block for Semiconducting Polymers. Journal of the American Chemical Society, 139(41), 14356-14359. https://doi.org/10.1021/jacs.7b07750

Naphthalene Bis(4,8-diamino-1,5-dicarboxyl)amide Building Block for Semiconducting Polymers. / Eckstein, Brian J.; Melkonyan, Ferdinand S.; Manley, Eric F.; Fabiano, Simone; Mouat, Aidan R.; Chen, Lin X.; Facchetti, Antonio; Marks, Tobin J.

In: Journal of the American Chemical Society, Vol. 139, No. 41, 18.10.2017, p. 14356-14359.

Research output: Contribution to journal › Article

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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.",

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AU - Fabiano, Simone

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AU - Facchetti, Antonio

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Access to Document

10.1021/jacs.7b07750