Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors
Głowacki, Eric Daniel
White, Matthew Schuette
Sariciftci, Niyazi Serdar
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CitationGłowacki, Eric Daniel, Halime Coskun, Martin A. Blood-Forsythe, Uwe Monkowius, Lucia Leonat, Marek Grzybowski, Daniel Gryko, Matthew Schuette White, Alán Aspuru-Guzik, and Niyazi Serdar Sariciftci. 2014. “Hydrogen-Bonded Diketopyrrolopyrrole (DPP) Pigments as Organic Semiconductors.” Organic Electronics 15 (12) (December): 3521–3528. doi:10.1016/j.orgel.2014.09.038.
AbstractDiketopyrrolopyrroles (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 Hbonded crystal lattice supports close and relatively cofacial p–p 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.
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