title: Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors.
abstract: Diketopyrrolopyrroles (DPPs) have recently gained attention as building-blocks for organic semiconducting polymers and small molecules, however the semiconducting properties of their hydrogen-bonded (H-bonded) pigment forms have not been explored. Herein we report on the performance of three archetypical H-bonded DPP pigments, which show ambipolar carrier mobilities in the range 0.01-0.06 cm2/V s in organic field-effect transistors. Their semiconducting properties are correlated with crystal structure, where an H-bonded crystal lattice supports close and relatively cofacial π-π stacking. To better understand transport in these systems, density functional theory calculations were carried out, indicating theoretical maximum ambipolar mobility values of ∼0.3 cm2/V s. Based on these experimental and theoretical results, H-bonded DPPs represent a viable alternative to more established DPP-containing polymers and small molecules where H-bonding is blocked by N-alkylation.
authors: Linz Institute for Organic Solar Cells (LIOS), Physical Chemistry, Johannes Kepler University, Linz, Austria.
authors: Eric Daniel
authors: ED
authors: Głowacki
authors: Linz Institute for Organic Solar Cells (LIOS), Physical Chemistry, Johannes Kepler University, Linz, Austria.
authors: Halime
authors: H
authors: Coskun
authors: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, USA.
authors: Martin A
authors: MA
authors: Blood-Forsythe
authors: Institute of Inorganic Chemistry, Johannes Kepler University, Linz, Austria.
authors: Uwe
authors: U
authors: Monkowius
authors: Linz Institute for Organic Solar Cells (LIOS), Physical Chemistry, Johannes Kepler University, Linz, Austria.
authors: Lucia
authors: L
authors: Leonat
authors: Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland.
authors: Marek
authors: M
authors: Grzybowski
authors: Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland.
authors: Daniel
authors: D
authors: Gryko
authors: Linz Institute for Organic Solar Cells (LIOS), Physical Chemistry, Johannes Kepler University, Linz, Austria.
authors: Matthew Schuette
authors: MS
authors: White
authors: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, USA.
authors: Alán
authors: A
authors: Aspuru-Guzik
authors: Linz Institute for Organic Solar Cells (LIOS), Physical Chemistry, Johannes Kepler University, Linz, Austria.
authors: Niyazi Serdar
authors: NS
authors: Sariciftci
keywords: DFT calculations; Diketopyrrolopyrrole; Hydrogen-bonding; Organic field-effect transistors; Organic pigments
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