Helicene Aromaticity Deviates from the Clar Rule ‐ On the Electronic Dissimilarity of Large Isomeric Fibonacenes - Archive ouverte HAL Access content directly
Journal Articles Angewandte Chemie International Edition Year : 2024

Helicene Aromaticity Deviates from the Clar Rule ‐ On the Electronic Dissimilarity of Large Isomeric Fibonacenes

Abstract

This combined experimental and theoretical study illustrates the profound consequences of non‐planarity on the electronic properties of polycyclic arenes. Three isomeric [10]fibonacene tetraesters were synthesized through a robust and regiocontrolled Perkin/Mallory approach: a nearly planar [10]phenacene derivative, a moderately twisted [10]semicircle derivative, and a 3D non‐planar [10]helicene derivative. The photophysical properties of the 3D [10]helicene isomer were found to be dramatically different from the comparable ones of the [10]phenacene and [10]semicircle isomers. The aromatic properties of the [10]phenacene and [10]semicircle isomers conform well with their predictive Kekulé and Clar analyses, but the [10]helicene isomer deviates from these general topological rules, which appears to be a general phenomenon for [n]fibonacenes with n ≥ 9.
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Thursday, October 3, 2024
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Thursday, October 3, 2024
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Dates and versions

hal-04541582 , version 1 (10-04-2024)

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Ludmilla Sturm, Albert Artigas, Yoann Coquerel, Ivan Bechtold, Fabien Durola, et al.. Helicene Aromaticity Deviates from the Clar Rule ‐ On the Electronic Dissimilarity of Large Isomeric Fibonacenes. Angewandte Chemie International Edition, 2024, ⟨10.1002/anie.202403170⟩. ⟨hal-04541582⟩
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