Star-Shaped Conjugated Molecules with Oxa- or Thiadiazole Bithiophene Side Arms

Kamil Kotwica , Anastasia Kostyuchenko , Przemysław Data , Tomasz Marszałek , Łukasz Skórka , Tomasz Jaroch , Sylwia Kacka , Małgorzata Zagórska , Robert Nowakowski , Andrew P. Monkman , Aaleksander S. Fisyuk , Wojciech Pisula , Adam Proń

Abstract

Star-shaped conjugated molecules, consisting of a benzene central unit symmetrically trisubstituted with either oxa- or thiadiazole bithiophene groups, were synthesized as promising molecules and building blocks for application in (opto)electronics and electrochromic devices. Their optical (Eg(opt)) as well as electrochemical (Eg(electro)) band gaps depended on the type of the side arm and the number of solubilizing alkyl substituents. Oxadiazole derivatives showed Eg(opt) slightly below 3 eV and by 0.2 eV larger than those determined for thiadiazole-based compounds. The presence of alkyl substituents in the arms additionally lowered the band gap. The obtained compounds were efficient electroluminophores in guest/host-type light-emitting diodes. They also showed a strong tendency to self-organize in monolayers deposited on graphite, as evidenced by scanning tunneling microscopy. The structural studies by X-ray scattering revealed the formation of supramolecular columnar stacks in which the molecules were organized. Differences in macroscopic alignment in the specimen indicated variations in the self-assembly mechanism between the molecules. The compounds as trifunctional monomers were electrochemically polymerized to yield the corresponding polymer network. As shown by UV/Vis-NIR spectroelectrochemical studies, these networks exhibited reversible electrochromic behavior both in the oxidation and in the reduction modes. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Author Kamil Kotwica KChTP
Kamil Kotwica,,
- Chair Of Polymer Chemistry And Technology
, Anastasia Kostyuchenko
Anastasia Kostyuchenko,,
-
, Przemysław Data
Przemysław Data,,
-
, Tomasz Marszałek
Tomasz Marszałek,,
-
, Łukasz Skórka KChTP
Łukasz Skórka,,
- Chair Of Polymer Chemistry And Technology
, Tomasz Jaroch - Institute of Physical Chemistry Polish Academy of Sciences (IChF PAN)
Tomasz Jaroch,,
-
, Sylwia Kacka KChTP
Sylwia Kacka,,
- Chair Of Polymer Chemistry And Technology
, Małgorzata Zagórska KChTP
Małgorzata Zagórska,,
- Chair Of Polymer Chemistry And Technology
, Robert Nowakowski - Institute of Physical Chemistry Polish Academy of Sciences (IChF PAN)
Robert Nowakowski,,
-
, Andrew P. Monkman
Andrew P. Monkman,,
-
et al.
Journal seriesChemistry-A European Journal, ISSN 0947-6539
Issue year2016
Vol22
No33
Pages11795-11806
Publication size in sheets0.55
Keywords in Englishelectron transport; host–guest systems; self-assembly; semiconductors; supramolecular chemistry
DOIDOI:10.1002/chem.201600984
URL https://www.scopus.com/inward/record.uri?eid=2-s2.0-84979902021&doi=10.1002%2fchem.201600984&partnerID=40&md5=ba810b83cd3c07e74c27c0789a0bb0b2
Languageen angielski
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wdpb_publikacje_pliki_plik_publikacja_2893_org.pdf (file archived - login or check accessibility on faculty) wdpb_publikacje_pliki_plik_publikacja_2893_org.pdf 1.49 MB
Score (nominal)40
ScoreMinisterial score = 40.0, 28-11-2017, ArticleFromJournal
Ministerial score (2013-2016) = 40.0, 28-11-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 5.317 (2) - 2016=5.184 (5)
Citation count*9 (2018-02-19)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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