Revisiting Kekulene: Synthesis and Single-Molecule Imaging

[Image: see text] 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 re...

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Autores principales: Pozo, Iago, Majzik, Zsolt, Pavliček, Niko, Melle-Franco, Manuel, Guitián, Enrique, Peña, Diego, Gross, Leo, Pérez, Dolores
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6786662/
https://www.ncbi.nlm.nih.gov/pubmed/31525873
http://dx.doi.org/10.1021/jacs.9b07926
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author Pozo, Iago
Majzik, Zsolt
Pavliček, Niko
Melle-Franco, Manuel
Guitián, Enrique
Peña, Diego
Gross, Leo
Pérez, Dolores
author_facet Pozo, Iago
Majzik, Zsolt
Pavliček, Niko
Melle-Franco, Manuel
Guitián, Enrique
Peña, Diego
Gross, Leo
Pérez, Dolores
author_sort Pozo, Iago
collection PubMed
description [Image: see text] 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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spelling pubmed-67866622019-10-11 Revisiting Kekulene: Synthesis and Single-Molecule Imaging Pozo, Iago Majzik, Zsolt Pavliček, Niko Melle-Franco, Manuel Guitián, Enrique Peña, Diego Gross, Leo Pérez, Dolores J Am Chem Soc [Image: see text] 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. American Chemical Society 2019-09-17 2019-10-02 /pmc/articles/PMC6786662/ /pubmed/31525873 http://dx.doi.org/10.1021/jacs.9b07926 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Pozo, Iago
Majzik, Zsolt
Pavliček, Niko
Melle-Franco, Manuel
Guitián, Enrique
Peña, Diego
Gross, Leo
Pérez, Dolores
Revisiting Kekulene: Synthesis and Single-Molecule Imaging
title Revisiting Kekulene: Synthesis and Single-Molecule Imaging
title_full Revisiting Kekulene: Synthesis and Single-Molecule Imaging
title_fullStr Revisiting Kekulene: Synthesis and Single-Molecule Imaging
title_full_unstemmed Revisiting Kekulene: Synthesis and Single-Molecule Imaging
title_short Revisiting Kekulene: Synthesis and Single-Molecule Imaging
title_sort revisiting kekulene: synthesis and single-molecule imaging
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6786662/
https://www.ncbi.nlm.nih.gov/pubmed/31525873
http://dx.doi.org/10.1021/jacs.9b07926
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