Jump to main content
Jump to site search


N-Cyanoimine as an electron-withdrawing functional group for organic semiconductors: example of dihydroindacenodithiophene positional isomers

Author affiliations

Abstract

Manipulating frontier molecular orbitals by chemical design is one of the chief aspects of organic electronics. For applications in the field of n-type organic field-effect transistors (OFET), depressing the LUMO energy level is particularly important to ensure efficient charge injection. In this work, we report the incorporation of electron-withdrawing cyanoimine functional groups on the bridges of dihydroindacenodithiophene regioisomers. Cyanoimines are barely known in the field of organic electronics but herein have been found to be highly efficient in depressing the LUMO energy level of an organic semiconductor and can thus be envisaged as an attractive alternative to widely known electron-withdrawing units such as dicyanovinylene. This work focuses on a detailed structure–property relationship study, including the incorporation in n-type OFETs, of two dihydroindacenodithiophene regioisomers bearing two cyanoimine groups either in a syn- or an anti-configuration. As far as we know, this work is only the second example reported to date on N-cyanoimines incorporated in n-type OFETs, and shows the potential of these functional groups in organic electronics.

Graphical abstract: N-Cyanoimine as an electron-withdrawing functional group for organic semiconductors: example of dihydroindacenodithiophene positional isomers

Back to tab navigation

Supplementary files

Publication details

The article was received on 28 Aug 2018, accepted on 11 Oct 2018 and first published on 15 Oct 2018


Article type: Paper
DOI: 10.1039/C8TC04313B
Citation: J. Mater. Chem. C, 2018, Advance Article
  •   Request permissions

    N-Cyanoimine as an electron-withdrawing functional group for organic semiconductors: example of dihydroindacenodithiophene positional isomers

    J. Peltier, B. Heinrich, B. Donnio, O. Jeannin, J. Rault-Berthelot, E. Jacques and C. Poriel, J. Mater. Chem. C, 2018, Advance Article , DOI: 10.1039/C8TC04313B

Search articles by author

Spotlight

Advertisements