Stabilization of acenes: 'Geländer'-pentacenes
We report soluble tetrakis-biphenyl substituted pentacenes comprised of sp2 carbons and synthesized from pentacene-5,7,12,14-tetraone. Intramolecular Yamamoto coupling of two tetrakis(chlorobiphenylyl)pentacenes yields helical, doubly wrapped pentacenes, in which the quaterphenylene units solubilize...
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| Hauptverfasser: | , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
05 January 2024
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| In: |
Angewandte Chemie. International edition
Year: 2024, Jahrgang: 63, Heft: 13, Pages: 1-5 |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.202316902 |
| Online-Zugang: | Verlag, kostenfrei, Volltext: https://doi.org/10.1002/anie.202316902 Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.202316902 
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| Verfasserangaben: | Philipp Ludwig, Frank Rominger, Jan Freudenberg and Uwe H.F. Bunz |
| Zusammenfassung: | We report soluble tetrakis-biphenyl substituted pentacenes comprised of sp2 carbons and synthesized from pentacene-5,7,12,14-tetraone. Intramolecular Yamamoto coupling of two tetrakis(chlorobiphenylyl)pentacenes yields helical, doubly wrapped pentacenes, in which the quaterphenylene units solubilize the pentacenes and shield their central anthracene units to an unprecedented degree. The criss-cross-bridged pentacenes resist (photo)oxidation, Diels-Alder reactions and are much less reactive than TIPS-ethynylated pentacene. Extension of this concept might provide access to the larger acenes. |
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| Beschreibung: | Gesehen am 22.02.2024 |
| Beschreibung: | Online Resource |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.202316902 |