Abstract
AbstractA 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 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.
Highlights
A new strategy is demonstrated for the synthesis of warped, negatively curved, all-sp2-carbon p-scaffolds
Multifold CÀC coupling reactions are used to transform a polyaromatic borinic acid into a saddle-shaped polyaromatic hydrocarbon (2) bearing two heptagonal rings. This Schwarzite substructure is synthesized in only two steps from an unfunctionalized alkene
Extended 2D frameworks of sp2-hybridized carbon continue to provoke scientific attention for their fascinating chemical, electronic, magnetic and photophysical properties.[1]. Diverse structures such as graphene, polycyclic aromatic hydrocarbon (PAH) “nanographenes,” carbon nanotubes, and fullerenes have had a revolutionary impact on diverse fields such as photovoltaics, host-guest chemistry, and organic electronics
Summary
A new strategy is demonstrated for the synthesis of warped, negatively curved, all-sp2-carbon p-scaffolds. Inclusion of curvature has been identified as an intriguing way to manipulate electronics and to impart dynamic structural behavior in sp2 carbon frameworks.[2] Curved compounds often show improved solubility and fluorescence properties compared to their planar counterparts.
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