%0 Journal Article %1 Farrell_2019 %A Farrell, Jeffrey M. %A Grande, Vincenzo %A Schmidt, David %A Würthner, Frank %D 2019 %I Wiley %J Angew. Chem. Int. Ed. %K myown %N 46 %P 16504 –16507 %R 10.1002/anie.201909975 %T A Highly Warped Heptagon-Containing sp² Carbon Scaffold via Vinylnaphthyl π-Extension %U https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201909975 %V 58 %X Abstract: A new strategy is demonstrated for the synthesis of warped, negatively curved, all-sp2-carbon p-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 p-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.

@article{Farrell_2019, abstract = {Abstract: A new strategy is demonstrated for the synthesis of warped, negatively curved, all-sp2-carbon p-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 p-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.}, added-at = {2019-11-12T13:49:36.000+0100}, author = {Farrell, Jeffrey M. and Grande, Vincenzo and Schmidt, David and Würthner, Frank}, biburl = {https://www.bibsonomy.org/bibtex/2a0bf8c4955f6995199408092bc835613/wuerthner_group}, doi = {10.1002/anie.201909975}, interhash = {cb50a8eceb2f6800e66cf5935bc8a69c}, intrahash = {a0bf8c4955f6995199408092bc835613}, journal = {Angew. Chem. Int. Ed.}, keywords = {myown}, month = sep, number = 46, pages = {16504 –16507}, publisher = {Wiley}, timestamp = {2020-06-29T13:59:50.000+0200}, title = {A Highly Warped Heptagon-Containing sp² Carbon Scaffold via Vinylnaphthyl π-Extension}, url = {https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201909975}, volume = 58, year = 2019 }