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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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Bibliographic Details
Main Authors: Ludwig, Philipp (Author) , Rominger, Frank (Author) , Freudenberg, Jan (Author) , Bunz, Uwe H. F. (Author)
Format: Article (Journal)
Language:English
Published: 05 January 2024
In: Angewandte Chemie. International edition
Year: 2024, Volume: 63, Issue: 13, Pages: 1-5
ISSN:1521-3773
DOI:10.1002/anie.202316902
Online Access: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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Author Notes:Philipp Ludwig, Frank Rominger, Jan Freudenberg and Uwe H.F. Bunz
Description
Summary: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.
Item Description:Gesehen am 22.02.2024
Physical Description:Online Resource
ISSN:1521-3773
DOI:10.1002/anie.202316902

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