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Stability of shielded pentacenes under ambient conditions

The stabilization of pentacene through variation of substituents serves as a test bed to access stable organic semiconductors, transferable to the larger soluble acenes and azaacenes. Pentacene is stable enough for derivatization via wet-chemistry but sufficiently labile to test its (induced) (photo...

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Hauptverfasser: Ludwig, Philipp (VerfasserIn) , Kilian, Paul (VerfasserIn) , Mayerhofer, Patrick (VerfasserIn) , Hippchen, Nikolai (VerfasserIn) , Rominger, Frank (VerfasserIn) , Freudenberg, Jan (VerfasserIn) , Bunz, Uwe H. F. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: April 2025
In: Helvetica chimica acta
Year: 2025, Jahrgang: 108, Heft: 4, Pages: 1-7
ISSN:1522-2675
DOI:10.1002/hlca.202400161
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/hlca.202400161
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/10.1002/hlca.202400161
Volltext
Verfasserangaben:Philipp Ludwig, Paul Kilian, Patrick Mayerhofer, Nikolai Hippchen, Frank Rominger, Jan Freudenberg, and Uwe H.F. Bunz
Beschreibung
Zusammenfassung:The stabilization of pentacene through variation of substituents serves as a test bed to access stable organic semiconductors, transferable to the larger soluble acenes and azaacenes. Pentacene is stable enough for derivatization via wet-chemistry but sufficiently labile to test its (induced) (photo)decomposition. In this article, we describe the synthesis of shielded pentacenes, either via covalent jacketing with ester macrocycles or via steric shielding with biphenylyl substituents, together with attempts to access a bis(ortho-quaterphenyl) substituted Geländer pentacene. The photostability of the pentacenes is assessed under ambient conditions (air, light) to simulate handling under typical laboratory conditions and put into perspective with reference compounds, such as TIPS-ethynylated, ether-jacketed or our previously reported Geländer pentacenes.
Beschreibung:Online veröffentlicht: 28. November 2024
Gesehen am 25.09.2025
Beschreibung:Online Resource
ISSN:1522-2675
DOI:10.1002/hlca.202400161

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