Preparation and characterization of new bioinspired molecules for organic electronics

Jan Richtár

Brno University of Technology, Faculty of Chemistry

In the present proposal we consider naturally occurring organic nitrogen-rich materials, as a
promising environmentally friendly electron-transporting materials for organic-electronic devices.

Our attention is focused on the synthesis of the pyrazine type of molecules depicted on picture 1.
The new pyrazine approach consists of two different building blocks (R, A) arranged in original
manner. Part A represents the strong electron-withdrawing diimide functional groups. Their highly
extended π-conjugated structure produce strong π−π intermolecular interaction, and the controllable
physicochemical properties by introducing a variety of alkyl chains on the N-position in diimide
group [1]. On the other hand, R represents more sophisticated construction of aromatic and
heteroaromatic fragments for increasing the electron-accepting abilities through expansion of
π-system. In order to ensure the delicious tailoring of desired molecules, fragment R can be
modified by polyaromatic and polyheteroaromatic compounds containing electron-donating as well as
electron-withdrawing groups.

  Picture 1: Scheme of the synthesis of the target compounds. Central ring represent the pyrazine
 building block. A – electron-accepting diimide moiety. R – aromatic and heteroaromatic fragments.

Novel bioinspired-materials topic spreads the wide experience of our multidisciplinary team on the
field of preparation and characterization of smart organic systems [2,3].

References:

[1] Vasimalla S.; et al. Chem. Mater. 2014, 26, 4030-4037.

[2] Krajčovič J.; et al. Journal of Luminescence 2015, 167, 222-226.

[3] Krajčovič, J.; et al. Journal of Luminescence 2016, 2016, 175, 94-99.