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Updated: Feb 18, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
On-Surface Annulation Reaction Cascade for the Selective Synthesis of Diindenopyrene
Frank Eisenhut1, Thomas Lehmann1, Andreas Viertel2
1Institute for Materials Science, Max Bergmann Center of Biomaterials, and Center for Advancing Electronics Dresden, TU Dresden , 01069 Dresden, Germany.
Abstract:
We investigated the thermally induced on-surface cyclization of 4,10-bis(2'-bromo-4'-methylphenyl)-1,3-dimethylpyrene to form the previously unknown, nonalternant polyaromatic hydrocarbon diindeno[1,2,3-cd:1',2',3'-mn]pyrene on Au(111) using scanning tunneling microscopy and spectroscopy. The observed unimolecular reaction involves thermally induced debromination followed by selective ring closure to fuse the neighboring benzene moieties via a five-membered ring. The structure of the product has been verified experimentally as well as theoretically. Our results demonstrate that on-surface reactions give rise to unusual chemical reactivities and selectivities and provide access to nonalternant polyaromatic molecules.
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