Bithiophenesulfonamide Building Block for π-Conjugated Donor-Acceptor Semiconductors

Ferdinand S. Melkonyan; Wei Zhao; Martin Drees; Nicholas D. Eastham; Matthew J. Leonardi; Melanie R. Butler; Zhihua Chen; Xinge Yu; Robert P.H. Chang; Mark A. Ratner; Antonio F. Facchetti; Tobin J. Marks

doi:10.1021/jacs.6b03498

Bithiophenesulfonamide Building Block for π-Conjugated Donor-Acceptor Semiconductors

Ferdinand S. Melkonyan, Wei Zhao, Martin Drees, Nicholas D. Eastham, Matthew J. Leonardi, Melanie R. Butler, Zhihua Chen, Xinge Yu, Robert P.H. Chang, Mark A. Ratner, Antonio F. Facchetti^*, Tobin J. Marks

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

53 Scopus citations

Abstract

We report here π-conjugated small molecules and polymers based on the new π-acceptor building block, bithiophenesulfonamide (BTSA). Molecular orbital computations and optical, electrochemical, and crystal structure analyses illuminate the architecture and electronic structure of the BTSA unit versus other acceptor building blocks. Field-effect transistors and photovoltaic cells demonstrate that BTSA is a promising unit for the construction of π-conjugated semiconducting materials.

Original language	English (US)
Pages (from-to)	6944-6947
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	22
DOIs	https://doi.org/10.1021/jacs.6b03498
State	Published - Jun 8 2016

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/jacs.6b03498

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title = "Bithiophenesulfonamide Building Block for π-Conjugated Donor-Acceptor Semiconductors",

abstract = "We report here π-conjugated small molecules and polymers based on the new π-acceptor building block, bithiophenesulfonamide (BTSA). Molecular orbital computations and optical, electrochemical, and crystal structure analyses illuminate the architecture and electronic structure of the BTSA unit versus other acceptor building blocks. Field-effect transistors and photovoltaic cells demonstrate that BTSA is a promising unit for the construction of π-conjugated semiconducting materials.",

author = "Melkonyan, {Ferdinand S.} and Wei Zhao and Martin Drees and Eastham, {Nicholas D.} and Leonardi, {Matthew J.} and Butler, {Melanie R.} and Zhihua Chen and Xinge Yu and Chang, {Robert P.H.} and Ratner, {Mark A.} and Facchetti, {Antonio F.} and Marks, {Tobin J.}",

note = "Funding Information: This research was supported in part by 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; F.S.M.), the ANSER Center (N.D.E. and M.J.L.), an Energy Frontier Research Center funded by the U.S. DOE, Office of Science, Office of Basic Energy Sciences under Award DE-SC0001059, and the Northwestern University Materials Research Science and Engineering Center under NSF Grant DMR-1121262 (X.Y., M.R.B.). M.R.B. was an NSF Predoctoral Fellow and M.J.L. an NDSEG Fellow. Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = jun,

day = "8",

doi = "10.1021/jacs.6b03498",

language = "English (US)",

volume = "138",

pages = "6944--6947",

journal = "Journal of the American Chemical Society",

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T1 - Bithiophenesulfonamide Building Block for π-Conjugated Donor-Acceptor Semiconductors

AU - Melkonyan, Ferdinand S.

AU - Zhao, Wei

AU - Drees, Martin

AU - Eastham, Nicholas D.

AU - Leonardi, Matthew J.

AU - Butler, Melanie R.

AU - Chen, Zhihua

AU - Yu, Xinge

AU - Chang, Robert P.H.

AU - Ratner, Mark A.

AU - Facchetti, Antonio F.

AU - Marks, Tobin J.

N1 - Funding Information: This research was supported in part by 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; F.S.M.), the ANSER Center (N.D.E. and M.J.L.), an Energy Frontier Research Center funded by the U.S. DOE, Office of Science, Office of Basic Energy Sciences under Award DE-SC0001059, and the Northwestern University Materials Research Science and Engineering Center under NSF Grant DMR-1121262 (X.Y., M.R.B.). M.R.B. was an NSF Predoctoral Fellow and M.J.L. an NDSEG Fellow. Publisher Copyright: © 2016 American Chemical Society.

PY - 2016/6/8

Y1 - 2016/6/8

N2 - We report here π-conjugated small molecules and polymers based on the new π-acceptor building block, bithiophenesulfonamide (BTSA). Molecular orbital computations and optical, electrochemical, and crystal structure analyses illuminate the architecture and electronic structure of the BTSA unit versus other acceptor building blocks. Field-effect transistors and photovoltaic cells demonstrate that BTSA is a promising unit for the construction of π-conjugated semiconducting materials.

AB - We report here π-conjugated small molecules and polymers based on the new π-acceptor building block, bithiophenesulfonamide (BTSA). Molecular orbital computations and optical, electrochemical, and crystal structure analyses illuminate the architecture and electronic structure of the BTSA unit versus other acceptor building blocks. Field-effect transistors and photovoltaic cells demonstrate that BTSA is a promising unit for the construction of π-conjugated semiconducting materials.

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Bithiophenesulfonamide Building Block for π-Conjugated Donor-Acceptor Semiconductors

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ASJC Scopus subject areas

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CCDC 1817194: Experimental Crystal Structure Determination

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Bithiophenesulfonamide Building Block for π-Conjugated Donor-Acceptor Semiconductors

Abstract

ASJC Scopus subject areas

UN SDGs

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CCDC 1817194: Experimental Crystal Structure Determination

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