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Issue 34, 2015
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Diketopyrrolopyrrole (DPP) functionalized tetrathienothiophene (TTA) small molecules for organic thin film transistors and photovoltaic cells

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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.

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

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Supplementary files

Article information


Submitted
12 May 2015
Accepted
31 Jul 2015
First published
03 Aug 2015

J. Mater. Chem. C, 2015,3, 8932-8941
Article type
Paper
Author version available

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

N. Zhou, S. Vegiraju, X. Yu, E. F. Manley, M. R. Butler, M. J. Leonardi, P. Guo, W. Zhao, Y. Hu, K. Prabakaran, R. P. H. Chang, M. A. Ratner, L. X. Chen, A. Facchetti, M. Chen and T. J. Marks, J. Mater. Chem. C, 2015, 3, 8932
DOI: 10.1039/C5TC01348H

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