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.
%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
}