Revisiting Kekulene: Synthesis and Single-Molecule Imaging | Zendy

Iago Pozo | Zendy; Zsolt Majzik | Zendy; Niko Pavliček | Zendy; Manuel MelleFranco | Zendy; Enrique Guitián | Zendy; Diego Peña | Zendy; Leo Groß | Zendy; Dolores Pérez | Zendy

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Revisiting Kekulene: Synthesis and Single-Molecule Imaging

Author(s) -

Iago Pozo,

Zsolt Majzik,

Niko Pavliček,

Manuel MelleFranco,

Enrique Guitián,

Diego Peña,

Leo Groß,

Dolores Pérez

Publication year - 2019

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.9b07926

Subject(s) - chemistry , synthon , molecule , computational chemistry , nanotechnology , stereochemistry , organic chemistry , materials science

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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