A Highly Warped Heptagon-Containing sp 2 Carbon Scaffold via Vinylnaphthyl π-Extension

A new strategy is demonstrated for the synthesis of warped, negatively curved, all-sp -carbon π-scaffolds. Multifold C-C coupling reactions are used to transform a polyaromatic borinic acid into a saddle-shaped polyaromatic hydrocarbon (2) bearing two heptagonal rings. Notably, this Schwarzite subst...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-11, Vol.58 (46), p.16504-16507
Main Authors: Farrell, Jeffrey M, Grande, Vincenzo, Schmidt, David, Würthner, Frank
Format: Article
Language:English
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Summary:A new strategy is demonstrated for the synthesis of warped, negatively curved, all-sp -carbon π-scaffolds. Multifold C-C coupling reactions are used to transform a polyaromatic borinic acid into a saddle-shaped polyaromatic hydrocarbon (2) bearing two heptagonal rings. Notably, this Schwarzite substructure is synthesized in only two steps from an unfunctionalized alkene. A highly warped structure of 2 was revealed by X-ray crystallographic studies and pronounced flexibility of this π-scaffold was ascertained by experimental and computational studies. Compound 2 exhibits excellent solubility, visible range absorption and fluorescence, and readily undergoes two reversible one-electron oxidations at mild potentials.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201909975