title: Low and High Molecular Mass Dithienopyrrole-Naphthalene Bisimide Donor-Acceptor Compounds: Synthesis, Electrochemical and Spectroelectrochemical Behaviour.
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)2undergoes 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.
authors.affiliation: Cardinal Stefan Wyszynski University, Faculty of Mathematics and Natural Sciences, School of Exact Sciences, Woycickiego 1/3, 01-938, Warsaw, Poland.|Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664, Warsaw, Poland.
authors.forename: Renata
authors.initials: R
authors.lastname: Rybakiewicz
authors.affiliation: Department of Science and Technology, Campus Norrköping, Linköpings Universitet, Bredgatan 33, 601 74, Norrköping, Sweden.
authors.forename: Eric D
authors.identifier: http://orcid.org/0000-0002-0280-8017
authors.initials: ED
authors.lastname: Glowacki
authors.affiliation: Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664, Warsaw, Poland.
authors.forename: Lukasz
authors.initials: L
authors.lastname: Skorka
authors.affiliation: Silesian University of Technology, Faculty of Chemistry, Strzody 9, 44-100, Gliwice, Poland.
authors.forename: Sandra
authors.initials: S
authors.lastname: Pluczyk
authors.affiliation: Silesian University of Technology, Faculty of Chemistry, Strzody 9, 44-100, Gliwice, Poland.
authors.forename: Pawel
authors.initials: P
authors.lastname: Zassowski
authors.affiliation: Linz Institute for Organic Solar Cells (LIOS), Physical Chemistry, Johannes Kepler Universität, Altenbergerstrasse 69, Linz, Austria.
authors.forename: Dogukan Hazar
authors.initials: DH
authors.lastname: Apaydin
authors.affiliation: Silesian University of Technology, Faculty of Chemistry, Strzody 9, 44-100, Gliwice, Poland.|Centre of Polymer and Carbon Materials, Polish Academy of Sciences, M. Curie-Sklodowska 34, 41-819, Zabrze, Poland.
authors.forename: Mieczyslaw
authors.initials: M
authors.lastname: Lapkowski
authors.affiliation: Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664, Warsaw, Poland.
authors.forename: Malgorzata
authors.initials: M
authors.lastname: Zagorska
authors.affiliation: Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664, Warsaw, Poland.
authors.forename: Adam
authors.initials: A
authors.lastname: Pron
keywords: dithienopyrrole; electrochemistry; naphthalene bisimide; photodiode; polymerization