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Triptycene end-capped quinoxalinophenanthrophenazines (QPPs): Influence of substituents and conditions on aggregation in the solid state

Triptycene end-capped quinoxalinophenanthrophenazine reveals a coplanar arrangement with a high overlap of the π planes. Four structurally related model compounds bearing electron-withdrawing or -donating groups were synthesized, and their optoelectronic properties were characterized by using cyclov...

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Hauptverfasser: Ueberricke, Lucas (VerfasserIn) , Holub, Daniel (VerfasserIn) , Kranz, Julian (VerfasserIn) , Rominger, Frank (VerfasserIn) , Elstner, Marcus (VerfasserIn) , Mastalerz, Michael (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 18 June 2019
In: Chemistry - a European journal
Year: 2019, Jahrgang: 25, Heft: 47, Pages: 11121-11134
ISSN:1521-3765
DOI:10.1002/chem.201902002
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201902002
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201902002
Volltext
Verfasserangaben:Lucas Ueberricke, Daniel Holub, Julian Kranz, Frank Rominger, Marcus Elstner, Michael Mastalerz
Beschreibung
Zusammenfassung:Triptycene end-capped quinoxalinophenanthrophenazine reveals a coplanar arrangement with a high overlap of the π planes. Four structurally related model compounds bearing electron-withdrawing or -donating groups were synthesized, and their optoelectronic properties were characterized by using cyclovoltammetry, absorption- and emission spectroscopy as well as theoretical calculations. The directional robustness of the triptycene end-capping of these compounds was tested by using single-crystal X-ray diffraction. The impact of solvents and crystallization conditions has also been investigated. In total, 17 single-crystal structures were obtained. Each structure was evaluated for its potential charge-transfer capability taking into account the overall molecular packing, solvent enclathration and the structural overlap of the π planes of adjacent molecules. For this purpose, charge-transfer integrals were also calculated for every π-stacked dimer.
Beschreibung:Gesehen am 19.03.2020
Beschreibung:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201902002

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