EPR and UV-vis spectroelectrochemical studies of diketopyrrolopyrroles disubstituted with alkylated thiophenes

Monika Góra , Sandra Pluczyk , Paweł Zassowski , Wojciech Krzywiec , Małgorzata Zagórska , Józef Mieczkowski , Mieczysław Łapkowski , Adam Proń


EPR and UV-vis spectroelectrochemical behavior of a series of ambipolar donor-acceptor-donor (DAD) compounds, consisting of a diketopyrrolopyrrole (DPP) central unit symmetrically disubstituted with mono-, bi- and terthiophene, is reported. All derivatives studied undergo a reversible reduction to radical anions at E ca. -1.55V to ca. -1.65V vs Fc/Fc+. Electrochemically generated radical anions are sufficiently stable to be detected at RT. Two-step oxidation of these compounds involves the formation of radical cations in the first step followed by their transformation into spinless dications in the second one. The formed radical cations are detectable at RT, however, contrary to the case of radical anions they yield unresolved EPR spectra. The potential of their formation depends on the length of D segment decreasing from ca. 0.50V vs Fc/Fc+ for monothiophene disubstituted DPP to ca. 0.25V in the case of the terthiophene derivative. Combining differential pulse voltammetry with EPR and UV-vis spectroelectrochemistry allows for unequivocal identification of all new, electrochemically induced UV-vis bands to particular forms of the studied molecules (radical anions, radical cations or dications). Both electrochemical reduction and electrochemical oxidation processes involve profound and distinctly different spectral changes in the visible range of the spectrum. Since they are reversible, the studied compounds can be considered as promising multicolor electrochromophores. © 2015 Elsevier Ltd.
Author Monika Góra (FC / CPCT)
Monika Góra,,
- Chair Of Polymer Chemistry And Technology
, Sandra Pluczyk - [Silesian University of Technology (PolSL)]
Sandra Pluczyk,,
- Politechnika Śląska
, Paweł Zassowski - [Silesian University of Technology (PolSL)]
Paweł Zassowski,,
- Politechnika Śląska
, Wojciech Krzywiec (FC / CPCT)
Wojciech Krzywiec,,
- Chair Of Polymer Chemistry And Technology
, Małgorzata Zagórska (FC / CPCT)
Małgorzata Zagórska,,
- Chair Of Polymer Chemistry And Technology
, Józef Mieczkowski - [Faculty of Chemistry (WChUW) [University of Warsaw (UW)]]
Józef Mieczkowski,,
- Wydział Chemii
, Mieczysław Łapkowski - [Politechnika Śląska]
Mieczysław Łapkowski,,
- Politechnika Śląska
, Adam Proń (FC / CPCT)
Adam Proń,,
- Chair Of Polymer Chemistry And Technology
Journal seriesSynthetic Metals, ISSN 0379-6779
Issue year2016
Publication size in sheets0.5
Keywords in EnglishDiketopyrrolopyrrole derivatives; Donor-acceptor semiconductors; EPR spectroelectrochemistry; Radical anions; Radical cations; UV-vis spectroelectrochemistry; ESR spectroscopy
ASJC Classification2505 Materials Chemistry; 2506 Metals and Alloys; 2210 Mechanical Engineering; 2211 Mechanics of Materials; 3104 Condensed Matter Physics; 2504 Electronic, Optical and Magnetic Materials
URL http://www.sciencedirect.com/science/article/pii/S0379677915300898
Languageen angielski
1-s2.0-S0379677915300898-main.pdf 2.48 MB
Score (nominal)30
Score sourcejournalList
ScoreMinisterial score = 30.0, 25-07-2020, ArticleFromJournal
Ministerial score (2013-2016) = 30.0, 25-07-2020, ArticleFromJournal
Publication indicators WoS Citations = 9; Scopus Citations = 7; GS Citations = 11.0; Scopus SNIP (Source Normalised Impact per Paper): 2016 = 0.764; WoS Impact Factor: 2016 = 2.435 (2) - 2016=2.165 (5)
Citation count*12 (2020-10-19)
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