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

Research output: Contribution to journalArticle

15 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 μe and μh of up to 0.39 and 0.32 cm2/(V·s), respectively.

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

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Semiconducting polymers
Semiconductors
Naphthalene
Amides
Polymers
Semiconductor materials
X-Ray Diffraction
Torsional stress
Charge transfer
Agglomeration
Copolymers
X ray diffraction
Molecules
naphthalene

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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 journalArticle

Eckstein, BJ, Melkonyan, FS, Manley, EF, Fabiano, S, Mouat, AR, Chen, LX, Facchetti, A & Marks, TJ 2017, 'Naphthalene Bis(4,8-diamino-1,5-dicarboxyl)amide Building Block for Semiconducting Polymers', Journal of the American Chemical Society, vol. 139, no. 41, pp. 14356-14359. https://doi.org/10.1021/jacs.7b07750
Eckstein, Brian J. ; Melkonyan, Ferdinand S. ; Manley, Eric F. ; Fabiano, Simone ; Mouat, Aidan R. ; Chen, Lin X. ; Facchetti, Antonio ; Marks, Tobin J. / Naphthalene Bis(4,8-diamino-1,5-dicarboxyl)amide Building Block for Semiconducting Polymers. In: Journal of the American Chemical Society. 2017 ; Vol. 139, No. 41. pp. 14356-14359.
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