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

Abstract

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 KChTP
Monika Góra,,
- Chair Of Polymer Chemistry And Technology
, Sandra Pluczyk - [Politechnika Śląska]
Sandra Pluczyk,,
-
- Politechnika Śląska
, Paweł Zassowski - [Politechnika Śląska]
Paweł Zassowski,,
-
- Politechnika Śląska
, Wojciech Krzywiec KChTP
Wojciech Krzywiec,,
- Chair Of Polymer Chemistry And Technology
, Małgorzata Zagórska KChTP
Małgorzata Zagórska,,
- Chair Of Polymer Chemistry And Technology
, Józef Mieczkowski - [Faculty of Chemistry (WChUW) [Uniwersytet Warszawski (UW)]]
Józef Mieczkowski,,
-
- Wydział Chemii
, Mieczysław Łapkowski - [Politechnika Śląska]
Mieczysław Łapkowski,,
-
- Politechnika Śląska
, Adam Proń KChTP
Adam Proń,,
- Chair Of Polymer Chemistry And Technology
Journal seriesSynthetic Metals, ISSN 0379-6779
Issue year2016
Vol216
Pages75-82
Publication size in sheets0.5
Keywords in EnglishDiketopyrrolopyrrole derivatives; Donor-acceptor semiconductors; EPR spectroelectrochemistry; Radical anions; Radical cations; UV-vis spectroelectrochemistry; ESR spectroscopy
DOIDOI:10.1016/j.synthmet.2015.09.012
URL http://www.sciencedirect.com/science/article/pii/S0379677915300898
Languageen angielski
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1-s2.0-S0379677915300898-main.pdf 2.48 MB
Score (nominal)30
ScoreMinisterial score = 30.0, 28-11-2017, ArticleFromJournal
Ministerial score (2013-2016) = 30.0, 28-11-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 2.435 (2) - 2016=2.165 (5)
Citation count*4 (2018-06-17)
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