Synthesis of a Helical Bilayer Nanographene |
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Authors: | Dr Paul J Evans Dr Jiangkun Ouyang Dr Ludovic Favereau Dr Jeanne Crassous Dr Israel Fernández Dr Josefina Perles Prof?Dr Nazario Martín |
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Institution: | 1. www.nazariomartingroup.com
0000-0003-3016-579X
Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Madrid, Spain;2. Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS—, Univ. Rennes, Rennes Cedex, France;3. Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Madrid, Spain;4. Single Crystal X-ray Diffraction Laboratory, Interdepartmental Research Service (SIdI), Universidad Autónoma de Madrid, Madrid, Spain;5. IMDEA-Nanociencia, C/Faraday, Madrid, Spain |
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Abstract: | 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. |
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Keywords: | arenes bilayer graphene chirality helicenes nanographene |
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