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Synthesis of a Helical Bilayer Nanographene
Author(s) -
Evans Paul J.,
Ouyang Jiangkun,
Favereau Ludovic,
Crassous Jeanne,
Fernández Israel,
Perles Josefina,
Martín Nazario
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201800798
Subject(s) - helicene , bilayer , materials science , bilayer graphene , linker , rigidity (electromagnetism) , crystallography , graphene , nanotechnology , chemistry , membrane , molecule , organic chemistry , composite material , biochemistry , computer science , operating system
A rigid, inherently chiral bilayer nanographene has been synthesized as both the racemate and enantioenriched M isomer (with 93 % ee ) in three steps from established helicenes. This folded nanographene is composed of two hexa‐ peri ‐hexabenzocoronene layers fused to a [10]helicene, with an interlayer distance of 3.6 Å as determined by X‐ray crystallography. The rigidity of the helicene linker forces the layers to adopt a nearly aligned AA‐stacked conformation, rarely observed in few‐layer graphene. By combining the advantages of nanographenes and helicenes, we have constructed a bilayer system of 30 fused benzene rings that is also chiral, rigid, and remains soluble in common organic solvents. We present this as a molecular model system of bilayer graphene, with properties of interest in a variety of potential applications.