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

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30 Citations (Scopus)

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 languageEnglish
Pages (from-to)8932-8941
Number of pages10
JournalJournal of Materials Chemistry C
Volume3
Issue number34
DOIs
Publication statusPublished - Jul 31 2015

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ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Chemistry

Cite this

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