Low and High Molecular Mass Dithienopyrrole-Naphthalene Bisimide Donor-Acceptor Compounds: Synthesis, Electrochemical and Spectroelectrochemical Behaviour

Renata Rybakiewicz; Eric D Glowacki; Lukasz Skorka; Sandra Pluczyk; Pawel Zassowski; Dogukan Hazar Apaydin; Mieczyslaw Lapkowski; Malgorzata Zagorska; Adam Pron

doi:10.1002/chem.201604672

Low and High Molecular Mass Dithienopyrrole-Naphthalene Bisimide Donor-Acceptor Compounds: Synthesis, Electrochemical and Spectroelectrochemical Behaviour

Chemistry. 2017 Feb 24;23(12):2839-2851. doi: 10.1002/chem.201604672. Epub 2017 Jan 30.

Authors

Affiliations

¹ Cardinal Stefan Wyszynski University, Faculty of Mathematics and Natural Sciences, School of Exact Sciences, Woycickiego 1/3, 01-938, Warsaw, Poland.
² Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664, Warsaw, Poland.
³ Department of Science and Technology, Campus Norrköping, Linköpings Universitet, Bredgatan 33, 601 74, Norrköping, Sweden.
⁴ Silesian University of Technology, Faculty of Chemistry, Strzody 9, 44-100, Gliwice, Poland.
⁵ Linz Institute for Organic Solar Cells (LIOS), Physical Chemistry, Johannes Kepler Universität, Altenbergerstrasse 69, Linz, Austria.
⁶ Centre of Polymer and Carbon Materials, Polish Academy of Sciences, M. Curie-Sklodowska 34, 41-819, Zabrze, Poland.

PMID: 28059477
DOI: 10.1002/chem.201604672

Abstract

Two low molecular weight electroactive donor-acceptor-donor (DAD)-type molecules are reported, namely naphthalene bisimide (NBI) symmetrically core-functionalized with dithienopyrrole (NBI-(DTP)₂ ) and an asymmetric core-functionalized naphthalene bisimide with dithienopyrrole (DTP) substituent on one side and 2-ethylhexylamine on the other side (NBI-DTP-NHEtHex). Both compounds are characterized by low optical bandgaps (1.52 and 1.65 eV, respectively). NBI-(DTP)₂ undergoes oxidative electropolymerization giving the electroactive polymer of ambipolar character. Its two-step reversible reduction and oxidation is corroborated by complementary EPR and UV/Vis-NIR spectroelectrochemical investigations. The polymer turned out to be electrochemically active not only in aprotic solvents but also in aqueous electrolytes, showing a distinct photocathodic current attributed to proton reduction. Additionally, poly(NBI-(DTP)₂ ) was successfully tested as a photodiode material.

Keywords: dithienopyrrole; electrochemistry; naphthalene bisimide; photodiode; polymerization.