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 › peer-review

18 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

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/jacs.7b07750

Fingerprint Dive into the research topics of 'Naphthalene Bis(4,8-diamino-1,5-dicarboxyl)amide Building Block for Semiconducting Polymers'. Together they form a unique fingerprint.

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 journal › Article › peer-review

@article{cfa1b5b75ccd42c9903378d28e021425,

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

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.",

author = "Eckstein, {Brian J.} and Melkonyan, {Ferdinand S.} and Manley, {Eric F.} and Simone Fabiano and Mouat, {Aidan R.} and Chen, {Lin X.} and Antonio Facchetti and Marks, {Tobin J}",

year = "2017",

month = oct,

day = "18",

doi = "10.1021/jacs.7b07750",

language = "English",

volume = "139",

pages = "14356--14359",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "41",

}

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

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.

UR - http://www.scopus.com/inward/record.url?scp=85031758979&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85031758979&partnerID=8YFLogxK

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 -