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A Family of Superhelicenes: Easily Tunable, Chiral Nanographenes by Merging Helicity with Planar π Systems
Author(s) -
Reger David,
Haines Philipp,
Amsharov Konstantin Y.,
Schmidt Julia A.,
Ullrich Tobias,
Bönisch Simon,
Hampel Frank,
Görling Andreas,
Nelson Jenny,
Jelfs Kim E.,
Guldi Dirk M.,
Jux Norbert
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202103253
Subject(s) - ring (chemistry) , enantiomer , planar , circular dichroism , helicity , chemistry , crystallography , materials science , stereochemistry , physics , computer science , organic chemistry , computer graphics (images) , particle physics
We designed a straightforward synthetic route towards a full‐fledged family of π‐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.