Revisiting Kekulene: Synthesis and Single-Molecule Imaging
Pozo, Iago; Majzik, Zsolt; Pavlicek, Niko; Melle-Franco, Manuel; Guitian, Enrique; Pena, Diego; Gross, Leo; Perez, Dolores
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
2019
VL / 141 - BP / 15488 - EP / 15493
abstract
Four decades after the first (and only) reported synthesis of kekulene, this emblematic cycloarene has been obtained again through an improved route involving the construction of a key synthetic intermediate, 5,6,8,9-tetrahydrobenzo[m]tetraphene, by means of a double Diels-Alder reaction between styrene and a versatile benzodiyne synthon. Ultra-high-resolution AFM imaging of single molecules of kekulene and computational calculations provide additional support for a molecular structure with a significant degree of bond localization in accordance with the resonance structure predicted by the Clar model.
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