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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| Main Authors: | , , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
April 2025
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| In: |
Helvetica chimica acta
Year: 2025, Volume: 108, Issue: 4, Pages: 1-7 |
| ISSN: | 1522-2675 |
| DOI: | 10.1002/hlca.202400161 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/hlca.202400161 Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/10.1002/hlca.202400161 
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| Author Notes: | Philipp Ludwig, Paul Kilian, Patrick Mayerhofer, Nikolai Hippchen, Frank Rominger, Jan Freudenberg, and Uwe H.F. Bunz |
| Summary: | 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. |
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| Item Description: | Online veröffentlicht: 28. November 2024 Gesehen am 25.09.2025 |
| Physical Description: | Online Resource |
| ISSN: | 1522-2675 |
| DOI: | 10.1002/hlca.202400161 |