Helical Bilayer Nonbenzenoid Nanographene Bearing a [10]Helicene with Two Embedded Heptagons |
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| Authors: | Lin Yang Dr Yang-Yang Ju Dr Miguel A Medel Dr Yubin Fu Dr Hartmut Komber Dr Evgenia Dmitrieva Dr Jin-Jiang Zhang Sebastian Obermann Prof?Dr Araceli G Campaña Dr Ji Ma Prof?Dr Xinliang Feng |
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| Institution: | 1. Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany;2. State Key Laboratory for Physical Chemistry of Solid Surfaces, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 China;3. Departamento de Química Orgánica, Unidad de Excelencia de Química (UEQ)., Facultad de Ciencias., Universidad de Granada, 18071 Granada, Spain;4. Leibniz-Institut für Polymerforschung Dresden e.V., Hohe Straße 6, 01069 Dresden, Germany;5. Leibniz Institute for Solid State and Materials Research, Helmholtzstr. 20, 01069 Dresden, Germany |
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| Abstract: | The precision synthesis of helical bilayer nanographenes (NGs) with new topology is of substantial interest because of their exotic physicochemical properties. However, helical bilayer NGs bearing non-hexagonal rings remain synthetically challenging. Here we present the efficient synthesis of the first helical bilayer nonbenzenoid nanographene ( HBNG1 ) from a tailor-made azulene-embedded precursor, which contains a novel 10]helicene backbone with two embedded heptagons. Single-crystal X-ray analysis reveals its highly twisted bilayer geometry with a record small interlayer distance of 3.2 Å among the reported helical bilayer NGs. Notably, the close interlayer distance between the two layers offers intramolecular through-space conjugation as revealed by in situ spectroelectrochemistry studies together with DFT simulations. Furthermore, the chiroptical properties of the P/M enantiomers of HBNG1 are also evaluated by circular dichroism and circularly polarized luminescence. |
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| Keywords: | Bilayer Chirality Helicene Heptagon Nanographene |
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