Adamantane substitutions: a path to high-performing, soluble, versatile and sustainable organic semiconducting materials

Novel ethyladamantyl solubilization side groups were found to induce π–π interactions between the conjugated cores through adamantyl–adamantyl stacking in soluble diketopyrrolopyrrole (DPP) derivatives. The closeness of the DPP cores amplifies charge transfer in the material, as far as the π–π inter...

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Published in:Journal of materials chemistry. C, Materials for optical and electronic devices Materials for optical and electronic devices, 2017, Vol.5 (19), p.4716-4723
Main Authors: Kovalenko, Alexander, Yumusak, Cigdem, Heinrichova, Patricie, Stritesky, Stanislav, Fekete, Ladislav, Vala, Martin, Weiter, Martin, Sariciftci, Niyazi Serdar, Krajcovic, Jozef
Format: Article
Language:English
Subjects:
Charge transfer
Crystallinity
Derivatives
Imides
Purification
Solubilization
Stacking
Sustainability
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Summary:Novel ethyladamantyl solubilization side groups were found to induce π–π interactions between the conjugated cores through adamantyl–adamantyl stacking in soluble diketopyrrolopyrrole (DPP) derivatives. The closeness of the DPP cores amplifies charge transfer in the material, as far as the π–π interaction is a dominant charge-hopping pathway. As a result, tenfold enhancement of hole mobilities exceeding those obtained for insoluble derivatives was reached. Moreover, due to high crystallinity and co-planarity of the conjugated cores, electron transfer was preserved with a mobility of 0.2 cm 2 V −1 s −1 for dithiophene-DPP. At the same time, the material remained soluble, which is a significant advantage for purification and processing. This approach can be universally applied for many types of semiconducting organic materials containing the imide motif, where solubilization is achieved by side-group substitution.
ISSN:2050-7526
2050-7534
DOI:10.1039/C6TC05076J