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Diels-Alder reactivity of triisopropylsilyl ethynyl substituted acenes

We investigated the Diels-Alder reaction of 6,13-bis(triisopropylsilylethynyl)pentacene (1) with small dienophiles such as (bridged) dihydronaphthalenes/cyclohexenes that yielded adducts at the central ring, the other dienophiles predominantly or exclusively attacked the unsubstituted off-center rin...

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Bibliographic Details
Main Authors: Jester, Fabian (Author) , Kaczun, Tobias (Author) , Maier, Steffen (Author) , Meiners, Paul (Author) , Weigold, Svenja (Author) , Rominger, Frank (Author) , Dreuw, Andreas (Author) , Freudenberg, Jan (Author) , Bunz, Uwe H. F. (Author)
Format: Article (Journal)
Language:English
Published: January 9, 2025
In: Chemistry - a European journal
Year: 2025, Volume: 31, Issue: 2, Pages: 1-6
ISSN:1521-3765
DOI:10.1002/chem.202403522
Online Access:Resolving-System, kostenfrei, Volltext: https://doi.org/10.1002/chem.202403522
Verlag, kostenfrei, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202403522
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Author Notes:Fabian Jester, Tobias Kaczun, Steffen Maier, Paul Meiners, Svenja Weigold, Frank Rominger, Andreas Dreuw, Jan Freudenberg, and Uwe H.F. Bunz
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Summary:We investigated the Diels-Alder reaction of 6,13-bis(triisopropylsilylethynyl)pentacene (1) with small dienophiles such as (bridged) dihydronaphthalenes/cyclohexenes that yielded adducts at the central ring, the other dienophiles predominantly or exclusively attacked the unsubstituted off-center ring. The difference in regioselectivity was investigated by DFT calculations. Apart from dispersion interactions, it is due to the steric demand of the dienophiles, which need to fit in between the silylethynyl substituents to react at the central ring. Epoxynaphthalene adducts of 1 as well as its anthracene and tetracene congeners were deoxygenated, easily furnishing triarenobarrelenes with TIPS-ethynyl substituents at the bridgeheads, attractive building blocks for porous solids and higher acene-based trimers.
Item Description:Online veröffentlicht: 17. Oktober 2024
Gesehen am 13.03.2025
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.202403522

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