Issue 19, 2017

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

Abstract

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 cm2 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.

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

Supplementary files

Article information

Article type
Paper
Submitted
22 Nov 2016
Accepted
13 Apr 2017
First published
13 Apr 2017

J. Mater. Chem. C, 2017,5, 4716-4723

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

A. Kovalenko, C. Yumusak, P. Heinrichova, S. Stritesky, L. Fekete, M. Vala, M. Weiter, N. S. Sariciftci and J. Krajcovic, J. Mater. Chem. C, 2017, 5, 4716 DOI: 10.1039/C6TC05076J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements