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Low and High Molecular Mass Dithienopyrrole–Naphthalene Bisimide Donor–Acceptor Compounds: Synthesis, Electrochemical and Spectroelectrochemical Behaviour
Author(s) -
Rybakiewicz Renata,
Glowacki Eric D.,
Skorka Lukasz,
Pluczyk Sandra,
Zassowski Pawel,
Apaydin Dogukan Hazar,
Lapkowski Mieczyslaw,
Zagorska Malgorzata,
Pron Adam
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604672
Subject(s) - photochemistry , chemistry , substituent , naphthalene , ambipolar diffusion , electrochemistry , acceptor , molecule , cyclic voltammetry , polymer chemistry , organic chemistry , electrode , physics , plasma , quantum mechanics , condensed matter physics
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.