TY  - JOUR
A1  - Farrell, Jeffrey  M.
A1  - Grande, Vincenzo
A1  - Schmidt, David
A1  - Würthner, Frank
T1  - A Highly Warped Heptagon-Containing sp\(^2\) Carbon Scaffold via Vinylnaphthyl π-Extension
JF  - Angewandte Chemie International Edition
N2  - A new strategy is demonstrated for the synthesis of warped, negatively curved, all‐sp\(^2\)‐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.
KW  - arenes
KW  - carbon
KW  - C-C coupling
KW  - curvature
KW  - polycyclic aromatic hydrocarbons
Y1  - 2019
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-206682
VL  - 58
IS  - 46
ER  -