Functionalized isothianaphthene monomers that promote quinoidal character in donor-acceptor copolymers for organic photovoltaics

Jessica D. Douglas; Gianmarco Griffini; Thomas W. Holcombe; Eric P. Young; Olivia P. Lee; Mark S. Chen; Jean Frechet

doi:10.1021/ma300589k

Functionalized isothianaphthene monomers that promote quinoidal character in donor-acceptor copolymers for organic photovoltaics

Jessica D. Douglas, Gianmarco Griffini, Thomas W. Holcombe, Eric P. Young, Olivia P. Lee, Mark S. Chen, Jean Frechet

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

50 Scopus citations

Abstract

A series of low band gap isothianaphthene-based (ITN) polymers with various electron-withdrawing substituents and intrinsic quinoidal character were synthesized, characterized, and tested in organic photovoltaic (OPV) devices. The three investigated ITN cores contained either ester, imide, or nitrile functionalities and were each synthesized in only four linear steps. The relative electron-withdrawing strength of the three substituents on the ITN moiety was evaluated and correlated to the optical and electronic properties of ITN-based copolymers. The ester- and imide-containing p-type polymers reached device efficiencies as high as 3% in bulk heterojunction blends with phenyl C 61-butyric acid methyl ester (PC 61BM), while the significantly electron-deficient nitrile-functionalized polymer behaved as an n-type material with an efficiency of 0.3% in bilayer devices with poly(3-(4-n-octyl)phenylthiophene) (POPT). © 2012 American Chemical Society.

Original language	English (US)
Pages (from-to)	4069-4074
Number of pages	6
Journal	Macromolecules
Volume	45
Issue number	10
DOIs	https://doi.org/10.1021/ma300589k
State	Published - May 3 2012

ASJC Scopus subject areas

Materials Chemistry
Organic Chemistry
Polymers and Plastics
Inorganic Chemistry

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10.1021/ma300589k

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@article{a42bd0060bfc4f60a3811f90b5d350be,

title = "Functionalized isothianaphthene monomers that promote quinoidal character in donor-acceptor copolymers for organic photovoltaics",

abstract = "A series of low band gap isothianaphthene-based (ITN) polymers with various electron-withdrawing substituents and intrinsic quinoidal character were synthesized, characterized, and tested in organic photovoltaic (OPV) devices. The three investigated ITN cores contained either ester, imide, or nitrile functionalities and were each synthesized in only four linear steps. The relative electron-withdrawing strength of the three substituents on the ITN moiety was evaluated and correlated to the optical and electronic properties of ITN-based copolymers. The ester- and imide-containing p-type polymers reached device efficiencies as high as 3% in bulk heterojunction blends with phenyl C 61-butyric acid methyl ester (PC 61BM), while the significantly electron-deficient nitrile-functionalized polymer behaved as an n-type material with an efficiency of 0.3% in bilayer devices with poly(3-(4-n-octyl)phenylthiophene) (POPT). {\textcopyright} 2012 American Chemical Society.",

author = "Douglas, {Jessica D.} and Gianmarco Griffini and Holcombe, {Thomas W.} and Young, {Eric P.} and Lee, {Olivia P.} and Chen, {Mark S.} and Jean Frechet",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported in part by the Director, Office of Science, Office of Basic Energy Sciences, Material Sciences and Engineering Division, of the U.S. Department of Energy under Contract DE-AC02-05CH11231 and the Frechet {"}Various Donors{"} gift fund for the support of research in new materials. G.G. thanks Fondazione Banca del Monte di Lombardia, T.W.H. thanks the National Science Foundation, and M.S.C. thanks the Camille and Henry Dreyfus Postdoctoral Program in Environmental Chemistry for fellowships. The authors also thank Professors Robert Bergman and Peter Vollhardt for helpful discussions.",

year = "2012",

month = may,

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doi = "10.1021/ma300589k",

language = "English (US)",

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pages = "4069--4074",

journal = "Macromolecules",

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publisher = "American Chemical Society",

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T1 - Functionalized isothianaphthene monomers that promote quinoidal character in donor-acceptor copolymers for organic photovoltaics

AU - Douglas, Jessica D.

AU - Griffini, Gianmarco

AU - Holcombe, Thomas W.

AU - Young, Eric P.

AU - Lee, Olivia P.

AU - Chen, Mark S.

AU - Frechet, Jean

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported in part by the Director, Office of Science, Office of Basic Energy Sciences, Material Sciences and Engineering Division, of the U.S. Department of Energy under Contract DE-AC02-05CH11231 and the Frechet "Various Donors" gift fund for the support of research in new materials. G.G. thanks Fondazione Banca del Monte di Lombardia, T.W.H. thanks the National Science Foundation, and M.S.C. thanks the Camille and Henry Dreyfus Postdoctoral Program in Environmental Chemistry for fellowships. The authors also thank Professors Robert Bergman and Peter Vollhardt for helpful discussions.

PY - 2012/5/3

Y1 - 2012/5/3

N2 - A series of low band gap isothianaphthene-based (ITN) polymers with various electron-withdrawing substituents and intrinsic quinoidal character were synthesized, characterized, and tested in organic photovoltaic (OPV) devices. The three investigated ITN cores contained either ester, imide, or nitrile functionalities and were each synthesized in only four linear steps. The relative electron-withdrawing strength of the three substituents on the ITN moiety was evaluated and correlated to the optical and electronic properties of ITN-based copolymers. The ester- and imide-containing p-type polymers reached device efficiencies as high as 3% in bulk heterojunction blends with phenyl C 61-butyric acid methyl ester (PC 61BM), while the significantly electron-deficient nitrile-functionalized polymer behaved as an n-type material with an efficiency of 0.3% in bilayer devices with poly(3-(4-n-octyl)phenylthiophene) (POPT). © 2012 American Chemical Society.

AB - A series of low band gap isothianaphthene-based (ITN) polymers with various electron-withdrawing substituents and intrinsic quinoidal character were synthesized, characterized, and tested in organic photovoltaic (OPV) devices. The three investigated ITN cores contained either ester, imide, or nitrile functionalities and were each synthesized in only four linear steps. The relative electron-withdrawing strength of the three substituents on the ITN moiety was evaluated and correlated to the optical and electronic properties of ITN-based copolymers. The ester- and imide-containing p-type polymers reached device efficiencies as high as 3% in bulk heterojunction blends with phenyl C 61-butyric acid methyl ester (PC 61BM), while the significantly electron-deficient nitrile-functionalized polymer behaved as an n-type material with an efficiency of 0.3% in bilayer devices with poly(3-(4-n-octyl)phenylthiophene) (POPT). © 2012 American Chemical Society.

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JO - Macromolecules

JF - Macromolecules

IS - 10

ER -

Functionalized isothianaphthene monomers that promote quinoidal character in donor-acceptor copolymers for organic photovoltaics

Abstract

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