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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 S•••S 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.

Authors:
 [1];  [2];  [3];  [3];  [3];  [3];  [1];  [4];  [4];  [2];  [1];  [3];  [3];  [5];  [2];  [6]
  1. Department of Materials Science and Engineering and Argonne Northwestern Solar Energy Research Center (ANSER); Northwestern University; Evanston, USA
  2. Department of Chemistry; National Central University; Taiwan, Republic of China
  3. Department of Chemistry and the Materials Research Center; the Argonne-Northwestern Solar Energy Research Center; Northwestern University; Evanston, USA
  4. Polyera Corporation; Skokie, USA
  5. Department of Chemistry and the Materials Research Center; the Argonne-Northwestern Solar Energy Research Center; Northwestern University; Evanston, USA; Polyera Corporation
  6. Department of Materials Science and Engineering and Argonne Northwestern Solar Energy Research Center (ANSER); Northwestern University; Evanston, USA; Department of Chemistry and the Materials Research Center; the Argonne-Northwestern Solar Energy Research Center
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC) (United States). Argonne-Northwestern Solar Energy Research Center (ANSER)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1370803
DOE Contract Number:
SC0001059
Resource Type:
Journal Article
Resource Relation:
Journal Name: Journal of Materials Chemistry. C; Journal Volume: 3; Journal Issue: 34; Related Information: ANSER partners with Northwestern University (lead); Argonne National Laboratory; University of Chicago; University of Illinois, Urbana-Champaign; Yale University
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 14 SOLAR ENERGY; catalysis (homogeneous), catalysis (heterogeneous), solar (photovoltaic), solar (fuels), photosynthesis (natural and artificial), bio-inspired, hydrogen and fuel cells, electrodes - solar, defects, charge transport, spin dynamics, membrane, materials and chemistry by design, optics, synthesis (novel materials), synthesis (self-assembly)

Citation Formats

Zhou, Nanjia, Vegiraju, Sureshraju, Yu, Xinge, Manley, Eric F., Butler, Melanie R., Leonardi, Matthew J., Guo, Peijun, Zhao, Wei, Hu, Yan, Prabakaran, Kumaresan, Chang, Robert P. H., Ratner, Mark A., Chen, Lin X., Facchetti, Antonio, Chen, Ming-Chou, and Marks, Tobin J.. Diketopyrrolopyrrole (DPP) functionalized tetrathienothiophene (TTA) small molecules for organic thin film transistors and photovoltaic cells. United States: N. p., 2015. Web. doi:10.1039/C5TC01348H.
Zhou, Nanjia, Vegiraju, Sureshraju, Yu, Xinge, Manley, Eric F., Butler, Melanie R., Leonardi, Matthew J., Guo, Peijun, Zhao, Wei, Hu, Yan, Prabakaran, Kumaresan, Chang, Robert P. H., Ratner, Mark A., Chen, Lin X., Facchetti, Antonio, Chen, Ming-Chou, & Marks, Tobin J.. Diketopyrrolopyrrole (DPP) functionalized tetrathienothiophene (TTA) small molecules for organic thin film transistors and photovoltaic cells. United States. doi:10.1039/C5TC01348H.
Zhou, Nanjia, Vegiraju, Sureshraju, Yu, Xinge, Manley, Eric F., Butler, Melanie R., Leonardi, Matthew J., Guo, Peijun, Zhao, Wei, Hu, Yan, Prabakaran, Kumaresan, Chang, Robert P. H., Ratner, Mark A., Chen, Lin X., Facchetti, Antonio, Chen, Ming-Chou, and Marks, Tobin J.. Thu . "Diketopyrrolopyrrole (DPP) functionalized tetrathienothiophene (TTA) small molecules for organic thin film transistors and photovoltaic cells". United States. doi:10.1039/C5TC01348H.
@article{osti_1370803,
title = {Diketopyrrolopyrrole (DPP) functionalized tetrathienothiophene (TTA) small molecules for organic thin film transistors and photovoltaic cells},
author = {Zhou, Nanjia and Vegiraju, Sureshraju and Yu, Xinge and Manley, Eric F. and Butler, Melanie R. and Leonardi, Matthew J. and Guo, Peijun and Zhao, Wei and Hu, Yan and Prabakaran, Kumaresan and Chang, Robert P. H. and Ratner, Mark A. and Chen, Lin X. and Facchetti, Antonio and Chen, Ming-Chou and Marks, Tobin J.},
abstractNote = {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 S•••S 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.},
doi = {10.1039/C5TC01348H},
journal = {Journal of Materials Chemistry. C},
number = 34,
volume = 3,
place = {United States},
year = {Thu Jan 01 00:00:00 EST 2015},
month = {Thu Jan 01 00:00:00 EST 2015}
}