Diketopyrrolopyrrole (DPP) functionalized tetrathienothiophene (TTA) small molecules for organic thin film transistors and photovoltaic cells

Nanjia Zhou; Sureshraju Vegiraju; Xinge Yu; Eric F. Manley; Melanie R. Butler; Matthew J. Leonardi; Peijun Guo; Wei Zhao; Yan Hu; Kumaresan Prabakaran; Robert P H Chang; Mark A. Ratner; Lin X. Chen; Antonio Facchetti; Ming Chou Chen; Tobin J. Marks

doi:10.1039/c5tc01348h

Diketopyrrolopyrrole (DPP) functionalized tetrathienothiophene (TTA) small molecules for organic thin film transistors and photovoltaic cells

Nanjia Zhou, Sureshraju Vegiraju, Xinge Yu, Eric F. Manley, Melanie R. Butler, Matthew J. Leonardi, Peijun Guo, Wei Zhao, Yan Hu, Kumaresan Prabakaran, Robert P H Chang, Mark A. Ratner, Lin X. Chen, Antonio Facchetti^*, Ming Chou Chen, Tobin J. Marks

^*Corresponding author for this work

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

47 Scopus citations

Abstract

Two novel π-conjugated small molecules based on the electron-deficient diketopyrrolopyrrole (DPP) and the electron-rich fused tetrathienoacene (TTA) frameworks are synthesized and characterized. As verified in the bandgap compression of these chromophores by electrochemistry and density functional theory (DFT) computation, these DPP-TAA derivatives exhibit substantial conjugation and ideal MO energetics for light absorption. The large fused TTA core and strong intermolecular SS interactions enforce excellent molecular planarity, favoring a close-packed thin film morphologies for efficient charge transport, as indicated by grazing incidence wide angle X-ray scattering (GIWAXS), atomic force microscopy (AFM), and transmission electron microscopy (TEM) analysis. Top-gate/bottom-contact thin film transistors based on these systems exhibit hole mobilities approaching 0.1 cm² V^-1 s^-1. Organic photovoltaic cells based on DDPP-TTAR:PC₇₁BM blends achieve power conversion efficiencies (PCE) > 4% by systematic morphology tuning and judicious solvent additive selection.

Original language	English (US)
Pages (from-to)	8932-8941
Number of pages	10
Journal	Journal of Materials Chemistry C
Volume	3
Issue number	34
DOIs	https://doi.org/10.1039/c5tc01348h
State	Published - Jul 31 2015

ASJC Scopus subject areas

General Chemistry
Materials Chemistry

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Zhou, N., Vegiraju, S., Yu, X., Manley, E. F., Butler, M. R., Leonardi, M. J., Guo, P., Zhao, W., Hu, Y., Prabakaran, K., Chang, R. P. H., Ratner, M. A., Chen, L. X., Facchetti, A., Chen, M. C., & Marks, T. J. (2015). Diketopyrrolopyrrole (DPP) functionalized tetrathienothiophene (TTA) small molecules for organic thin film transistors and photovoltaic cells. Journal of Materials Chemistry C, 3(34), 8932-8941. https://doi.org/10.1039/c5tc01348h

@article{8881d1ec99c9432c82ffa64e1a3d2bfd,

title = "Diketopyrrolopyrrole (DPP) functionalized tetrathienothiophene (TTA) small molecules for organic thin film transistors and photovoltaic cells",

abstract = "Two novel π-conjugated small molecules based on the electron-deficient diketopyrrolopyrrole (DPP) and the electron-rich fused tetrathienoacene (TTA) frameworks are synthesized and characterized. As verified in the bandgap compression of these chromophores by electrochemistry and density functional theory (DFT) computation, these DPP-TAA derivatives exhibit substantial conjugation and ideal MO energetics for light absorption. The large fused TTA core and strong intermolecular SS interactions enforce excellent molecular planarity, favoring a close-packed thin film morphologies for efficient charge transport, as indicated by grazing incidence wide angle X-ray scattering (GIWAXS), atomic force microscopy (AFM), and transmission electron microscopy (TEM) analysis. Top-gate/bottom-contact thin film transistors based on these systems exhibit hole mobilities approaching 0.1 cm2 V-1 s-1. Organic photovoltaic cells based on DDPP-TTAR:PC71BM blends achieve power conversion efficiencies (PCE) > 4% by systematic morphology tuning and judicious solvent additive selection.",

author = "Nanjia Zhou and Sureshraju Vegiraju and Xinge Yu and Manley, {Eric F.} and Butler, {Melanie R.} and Leonardi, {Matthew J.} and Peijun Guo and Wei Zhao and Yan Hu and Kumaresan Prabakaran and Chang, {Robert P H} and Ratner, {Mark A.} and Chen, {Lin X.} and Antonio Facchetti and Chen, {Ming Chou} and Marks, {Tobin J.}",

note = "Publisher Copyright: {\textcopyright} 2015 The Royal Society of Chemistry.",

year = "2015",

month = jul,

day = "31",

doi = "10.1039/c5tc01348h",

language = "English (US)",

volume = "3",

pages = "8932--8941",

journal = "Journal of Materials Chemistry C",

issn = "2050-7534",

publisher = "Royal Society of Chemistry",

number = "34",

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Zhou, N, Vegiraju, S, Yu, X, Manley, EF, Butler, MR, Leonardi, MJ, Guo, P, Zhao, W, Hu, Y, Prabakaran, K, Chang, RPH , Ratner, MA , Chen, LX, Facchetti, A, Chen, MC & Marks, TJ 2015, 'Diketopyrrolopyrrole (DPP) functionalized tetrathienothiophene (TTA) small molecules for organic thin film transistors and photovoltaic cells', Journal of Materials Chemistry C, vol. 3, no. 34, pp. 8932-8941. https://doi.org/10.1039/c5tc01348h

TY - JOUR

T1 - Diketopyrrolopyrrole (DPP) functionalized tetrathienothiophene (TTA) small molecules for organic thin film transistors and photovoltaic cells

AU - Zhou, Nanjia

AU - Vegiraju, Sureshraju

AU - Yu, Xinge

AU - Manley, Eric F.

AU - Butler, Melanie R.

AU - Leonardi, Matthew J.

AU - Guo, Peijun

AU - Zhao, Wei

AU - Hu, Yan

AU - Prabakaran, Kumaresan

AU - Chang, Robert P H

AU - Ratner, Mark A.

AU - Chen, Lin X.

AU - Facchetti, Antonio

AU - Chen, Ming Chou

AU - Marks, Tobin J.

PY - 2015/7/31

Y1 - 2015/7/31

N2 - Two novel π-conjugated small molecules based on the electron-deficient diketopyrrolopyrrole (DPP) and the electron-rich fused tetrathienoacene (TTA) frameworks are synthesized and characterized. As verified in the bandgap compression of these chromophores by electrochemistry and density functional theory (DFT) computation, these DPP-TAA derivatives exhibit substantial conjugation and ideal MO energetics for light absorption. The large fused TTA core and strong intermolecular SS interactions enforce excellent molecular planarity, favoring a close-packed thin film morphologies for efficient charge transport, as indicated by grazing incidence wide angle X-ray scattering (GIWAXS), atomic force microscopy (AFM), and transmission electron microscopy (TEM) analysis. Top-gate/bottom-contact thin film transistors based on these systems exhibit hole mobilities approaching 0.1 cm2 V-1 s-1. Organic photovoltaic cells based on DDPP-TTAR:PC71BM blends achieve power conversion efficiencies (PCE) > 4% by systematic morphology tuning and judicious solvent additive selection.

AB - Two novel π-conjugated small molecules based on the electron-deficient diketopyrrolopyrrole (DPP) and the electron-rich fused tetrathienoacene (TTA) frameworks are synthesized and characterized. As verified in the bandgap compression of these chromophores by electrochemistry and density functional theory (DFT) computation, these DPP-TAA derivatives exhibit substantial conjugation and ideal MO energetics for light absorption. The large fused TTA core and strong intermolecular SS interactions enforce excellent molecular planarity, favoring a close-packed thin film morphologies for efficient charge transport, as indicated by grazing incidence wide angle X-ray scattering (GIWAXS), atomic force microscopy (AFM), and transmission electron microscopy (TEM) analysis. Top-gate/bottom-contact thin film transistors based on these systems exhibit hole mobilities approaching 0.1 cm2 V-1 s-1. Organic photovoltaic cells based on DDPP-TTAR:PC71BM blends achieve power conversion efficiencies (PCE) > 4% by systematic morphology tuning and judicious solvent additive selection.

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DO - 10.1039/c5tc01348h

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JO - Journal of Materials Chemistry C

JF - Journal of Materials Chemistry C

IS - 34

ER -

Diketopyrrolopyrrole (DPP) functionalized tetrathienothiophene (TTA) small molecules for organic thin film transistors and photovoltaic cells

Abstract

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