Low and High Molecular Mass Dithienopyrrole-Naphthalene Bisimide Donor-Acceptor Compounds: Synthesis, Electrochemical and Spectroelectrochemical Behaviour
2017 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 23, no 12, 2839-2851 p.Article in journal (Refereed) Published
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 corefunctionalized 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 electropolymeriza-tion 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.
Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH , 2017. Vol. 23, no 12, 2839-2851 p.
electrochemistry; dithienopyrrole; polymerization; naphthalene bisimide; photodiode
IdentifiersURN: urn:nbn:se:liu:diva-136343DOI: 10.1002/chem.201604672ISI: 000395774300016PubMedID: 28059477OAI: oai:DiVA.org:liu-136343DiVA: diva2:1087892
Funding Agencies|Polish-Norwegian Research Programme [Pol-Nor/210704/43/2013]; National Centre of Science in Poland (NCN) [2015/17/B/ST5/00179]; Doktoris-scholarship program for an innovative Silesia; European Union within European Social Fund; Wroclaw Centre for Networking and Supercomputing, WCSS, Wroclaw, Poland ; Austrian FWF [TRP 294-N19]; Knut and Alice Wallenberg foundation-Centre for Molecular Medicine2017-04-102017-04-102017-04-10