A Highly Warped Heptagon-Containing sp2 Carbon Scaffold via Vinylnaphthyl π-Extension.

摘要: A new strategy is demonstrated for the synthesis of warped, negatively curved, all-sp2 -carbon π-scaffolds. Multifold C-C coupling reactions are used to transform a polyaromatic borinic acid into saddle-shaped hydrocarbon (2) bearing two heptagonal rings. Notably, this Schwarzite substructure synthesized in only steps from an unfunctionalized alkene. highly warped structure 2 was revealed by X-ray crystallographic studies and pronounced flexibility π-scaffold ascertained experimental computational studies. Compound exhibits excellent solubility, visible range absorption fluorescence, readily undergoes reversible one-electron oxidations at mild potentials.