A Family of Superhelicenes: Easily Tunable, Chiral Nanographenes by Merging Helicity with Planar π Systems

We designed a straightforward synthetic route towards a full-fledged family of pi-extended helicenes: superhelicenes. They have two hexa-peri-hexabenzocoronenes (HBCs) in common that are connected via a central five-membered ring. By means of structurally altering this 5-membered ring, we realized a versatile library of molecular building blocks. Not only the superhelicene structure, but also their features are tuned with ease. In-depth physico-chemical characterizations served as a proof of concept thereof. The superhelicene enantiomers were separated, their circular dichroism was measured in preliminary studies and concluded with an enantiomeric assignment. Our work was rounded-off by crystal structure analyses. Mixed stacks of M- and P-isomers led to twisted molecular wires. Using such stacks, charge-carrier mobilities were calculated, giving reason to expect outstanding hole transporting properties.

Automated summary

A straightforward synthetic route was designed to create a family of pi-extended helicenes called superhelicenes. By altering the 5-membered ring, a versatile library of molecular building blocks was realized, allowing for easy tuning of both structure and features. Physico-chemical characterizations confirmed the concept, showing potential for outstanding hole transporting properties in charge-carrier mobilities.