Indolo-naphthyridine-6,13-dione thiophene building block for conjugated polymer electronics: Molecular origin of ultrahigh n-type mobility

Kealan J. Fallon; Nilushi Wijeyasinghe; Eric F. Manley; Stoichko D. Dimitrov; Syeda A. Yousaf; Raja S. Ashraf; Warren Duffy; Anne A.Y. Guilbert; David M.E. Freeman; Mohammed Al-Hashimi; Jenny Nelson; James R. Durrant; Lin X. Chen; Iain McCulloch; Tobin J. Marks; Tracey M. Clarke; Thomas D. Anthopoulos; Hugo Bronstein

doi:10.1021/acs.chemmater.6b03671

Indolo-naphthyridine-6,13-dione thiophene building block for conjugated polymer electronics: Molecular origin of ultrahigh n-type mobility

Kealan J. Fallon, Nilushi Wijeyasinghe, Eric F. Manley, Stoichko D. Dimitrov, Syeda A. Yousaf, Raja S. Ashraf, Warren Duffy, Anne A.Y. Guilbert, David M.E. Freeman, Mohammed Al-Hashimi, Jenny Nelson, James R. Durrant, Lin X. Chen, Iain McCulloch, Tobin J. Marks, Tracey M. Clarke, Thomas D. Anthopoulos, Hugo Bronstein^*

^*Corresponding author for this work

Physical Sciences and Engineering

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

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Abstract

Herein, we present the synthesis and characterization of four conjugated polymers containing a novel chromophore for organic electronics based on an indigoid structure. These polymers exhibit extremely small band gaps of ∼1.2 eV, impressive crystallinity, and extremely high n-type mobility exceeding 3 cm² V s^-1. The n-type charge carrier mobility can be correlated with the remarkably high crystallinity along the polymer backbone having a correlation length in excess of 20 nm. Theoretical analysis reveals that the novel polymers have highly rigid nonplanar geometries demonstrating that backbone planarity is not a prerequisite for either narrow band gap materials or ultrahigh mobilities. Furthermore, the variation in backbone crystallinity is dependent on the choice of comonomer. OPV device efficiencies up to 4.1% and charge photogeneration up to 1000 nm are demonstrated, highlighting the potential of this novel chromophore class in high-performance organic electronics.

Original language	English (US)
Pages (from-to)	8366-8378
Number of pages	13
Journal	Chemistry of Materials
Volume	28
Issue number	22
DOIs	https://doi.org/10.1021/acs.chemmater.6b03671
State	Published - Nov 22 2016

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering
Materials Chemistry

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Fallon, K. J., Wijeyasinghe, N., Manley, E. F., Dimitrov, S. D., Yousaf, S. A., Ashraf, R. S., Duffy, W., Guilbert, A. A. Y., Freeman, D. M. E., Al-Hashimi, M., Nelson, J., Durrant, J. R., Chen, L. X., McCulloch, I., Marks, T. J., Clarke, T. M., Anthopoulos, T. D., & Bronstein, H. (2016). Indolo-naphthyridine-6,13-dione thiophene building block for conjugated polymer electronics: Molecular origin of ultrahigh n-type mobility. Chemistry of Materials, 28(22), 8366-8378. https://doi.org/10.1021/acs.chemmater.6b03671

@article{fe4c26135cb84677a4f92b93bf04457d,

title = "Indolo-naphthyridine-6,13-dione thiophene building block for conjugated polymer electronics: Molecular origin of ultrahigh n-type mobility",

abstract = "Herein, we present the synthesis and characterization of four conjugated polymers containing a novel chromophore for organic electronics based on an indigoid structure. These polymers exhibit extremely small band gaps of ∼1.2 eV, impressive crystallinity, and extremely high n-type mobility exceeding 3 cm2 V s-1. The n-type charge carrier mobility can be correlated with the remarkably high crystallinity along the polymer backbone having a correlation length in excess of 20 nm. Theoretical analysis reveals that the novel polymers have highly rigid nonplanar geometries demonstrating that backbone planarity is not a prerequisite for either narrow band gap materials or ultrahigh mobilities. Furthermore, the variation in backbone crystallinity is dependent on the choice of comonomer. OPV device efficiencies up to 4.1% and charge photogeneration up to 1000 nm are demonstrated, highlighting the potential of this novel chromophore class in high-performance organic electronics.",

author = "Fallon, {Kealan J.} and Nilushi Wijeyasinghe and Manley, {Eric F.} and Dimitrov, {Stoichko D.} and Yousaf, {Syeda A.} and Ashraf, {Raja S.} and Warren Duffy and Guilbert, {Anne A.Y.} and Freeman, {David M.E.} and Mohammed Al-Hashimi and Jenny Nelson and Durrant, {James R.} and Chen, {Lin X.} and Iain McCulloch and Marks, {Tobin J.} and Clarke, {Tracey M.} and Anthopoulos, {Thomas D.} and Hugo Bronstein",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = nov,

day = "22",

doi = "10.1021/acs.chemmater.6b03671",

language = "English (US)",

volume = "28",

pages = "8366--8378",

journal = "Chemistry of Materials",

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Fallon, KJ, Wijeyasinghe, N, Manley, EF, Dimitrov, SD, Yousaf, SA, Ashraf, RS, Duffy, W, Guilbert, AAY, Freeman, DME, Al-Hashimi, M, Nelson, J, Durrant, JR, Chen, LX, McCulloch, I, Marks, TJ, Clarke, TM, Anthopoulos, TD & Bronstein, H 2016, 'Indolo-naphthyridine-6,13-dione thiophene building block for conjugated polymer electronics: Molecular origin of ultrahigh n-type mobility', Chemistry of Materials, vol. 28, no. 22, pp. 8366-8378. https://doi.org/10.1021/acs.chemmater.6b03671

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T1 - Indolo-naphthyridine-6,13-dione thiophene building block for conjugated polymer electronics

T2 - Molecular origin of ultrahigh n-type mobility

AU - Fallon, Kealan J.

AU - Wijeyasinghe, Nilushi

AU - Manley, Eric F.

AU - Dimitrov, Stoichko D.

AU - Yousaf, Syeda A.

AU - Ashraf, Raja S.

AU - Duffy, Warren

AU - Guilbert, Anne A.Y.

AU - Freeman, David M.E.

AU - Al-Hashimi, Mohammed

AU - Nelson, Jenny

AU - Durrant, James R.

AU - Chen, Lin X.

AU - McCulloch, Iain

AU - Marks, Tobin J.

AU - Clarke, Tracey M.

AU - Anthopoulos, Thomas D.

AU - Bronstein, Hugo

PY - 2016/11/22

Y1 - 2016/11/22

N2 - Herein, we present the synthesis and characterization of four conjugated polymers containing a novel chromophore for organic electronics based on an indigoid structure. These polymers exhibit extremely small band gaps of ∼1.2 eV, impressive crystallinity, and extremely high n-type mobility exceeding 3 cm2 V s-1. The n-type charge carrier mobility can be correlated with the remarkably high crystallinity along the polymer backbone having a correlation length in excess of 20 nm. Theoretical analysis reveals that the novel polymers have highly rigid nonplanar geometries demonstrating that backbone planarity is not a prerequisite for either narrow band gap materials or ultrahigh mobilities. Furthermore, the variation in backbone crystallinity is dependent on the choice of comonomer. OPV device efficiencies up to 4.1% and charge photogeneration up to 1000 nm are demonstrated, highlighting the potential of this novel chromophore class in high-performance organic electronics.

AB - Herein, we present the synthesis and characterization of four conjugated polymers containing a novel chromophore for organic electronics based on an indigoid structure. These polymers exhibit extremely small band gaps of ∼1.2 eV, impressive crystallinity, and extremely high n-type mobility exceeding 3 cm2 V s-1. The n-type charge carrier mobility can be correlated with the remarkably high crystallinity along the polymer backbone having a correlation length in excess of 20 nm. Theoretical analysis reveals that the novel polymers have highly rigid nonplanar geometries demonstrating that backbone planarity is not a prerequisite for either narrow band gap materials or ultrahigh mobilities. Furthermore, the variation in backbone crystallinity is dependent on the choice of comonomer. OPV device efficiencies up to 4.1% and charge photogeneration up to 1000 nm are demonstrated, highlighting the potential of this novel chromophore class in high-performance organic electronics.

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VL - 28

SP - 8366

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JO - Chemistry of Materials

JF - Chemistry of Materials

IS - 22

ER -

Indolo-naphthyridine-6,13-dione thiophene building block for conjugated polymer electronics: Molecular origin of ultrahigh n-type mobility

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