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

Kotwica, Kamil; Kostyuchenko, Anastasia S.; Data, Przemyslaw; Marszalek, Tomasz; Skorka, Lukasz; Jaroch, Tomasz; Kacka, Sylwia; Zagorska, Malgorzata; Nowakowski, Robert; Monkman, Andrew P.; Fisyuk, Alexander S.; Pisula, Wojciech; Pron, Adam

doi:10.1002/chem.201600984

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

Kotwica, Kamil; Kostyuchenko, Anastasia S.; Data, Przemyslaw; Marszalek, Tomasz; Skorka, Lukasz; Jaroch, Tomasz; Kacka, Sylwia; Zagorska, Malgorzata; Nowakowski, Robert; Monkman, Andrew P.; Fisyuk, Alexander S.; Pisula, Wojciech; Pron, Adam

Authors

Kamil Kotwica

Anastasia S. Kostyuchenko

Przemyslaw Data

Tomasz Marszalek

Lukasz Skorka

Tomasz Jaroch

Sylwia Kacka

Malgorzata Zagorska

Robert Nowakowski

Professor Andrew Monkman a.p.monkman@durham.ac.uk
Professor

Alexander S. Fisyuk

Wojciech Pisula

Adam Pron

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.

Citation

Kotwica, K., Kostyuchenko, A. S., Data, P., Marszalek, T., Skorka, L., Jaroch, T., …Pron, A. (2016). Star-Shaped Conjugated Molecules with Oxa- or Thiadiazole Bithiophene Side Arms. Chemistry - A European Journal, 22(33), 11795-11806. https://doi.org/10.1002/chem.201600984

Journal Article Type	Article
Online Publication Date	Jul 12, 2016
Publication Date	Aug 8, 2016
Deposit Date	May 16, 2017
Publicly Available Date	Aug 11, 2017
Journal	Chemistry - A European Journal
Print ISSN	0947-6539
Electronic ISSN	1521-3765
Publisher	Wiley
Peer Reviewed	Peer Reviewed
Volume	22
Issue	33
Pages	11795-11806
DOI	https://doi.org/10.1002/chem.201600984

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Copyright Statement
This is the peer reviewed version of the following article: K. Kotwica, A. S. Kostyuchenko, P. Data, T. Marszalek, L. Skorka, T. Jaroch, S. Kacka, M. Zagorska, R. Nowakowski, A. P. Monkman, A. S. Fisyuk, W. Pisula, A. Pron, Star-Shaped Conjugated Molecules with Oxa- or Thiadiazole Bithiophene Side Arms. Chemistry - A European Journal 2016, 22(33): 11795-11806, which has been published in final form at https://doi.org/10.1002/chem.201600984. This article may be used for non-commercial purposes in accordance With Wiley-VCH Terms and Conditions for self-archiving.