Impact of Chirality on Hydrogen-Bonded Supramolecular Assemblies and Photoconductivity of Diketopyrrolopyrrole Derivatives |
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Authors: | Dr Swann Militzer Nozomi Nishimura Nelson Ricardo Ávila-Rovelo Dr Wakana Matsuda Duncan Schwaller Dr Philippe J Mésini Prof Shu Seki Dr Amparo Ruiz-Carretero |
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Institution: | 1. CNRS, UPR22, University of Strasbourg, Institute Charles Sadron, 23 Rue du Loess, 67000 Strasbourg Cedex 2, France;2. Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan |
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Abstract: | Hydrogen bonds can efficiently guide the self-assembly of organic materials, enabling to tune the properties of the aggregation processes. In the case of π-conjugated materials, several parameters such as temperature, concentration and solvent can be used to modify the aggregation state while tuning the optoelectronic properties. Chirality can be included within the impacting parameters due to the differences in molecular packing. Here, chiral and achiral thiophene-capped diketopyrrolopyrrole derivatives were designed and synthesized containing amide bonds, with the aim to study the interplay between chiral assemblies and their stabilization through hydrogen-bonding. Differences in aggregation properties were observed with spectroscopy and microscopy, and a contactless microwave-based technique was used to study their intrinsic charge carrier mobility. The positive role of hydrogen-bonding has been highlighted and the differences between chiral and achiral compounds have been elucidated. |
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Keywords: | diketopyrrolopyrrole hydrogen-bonding organic electronics self-assembly supramolecular chirality |
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