Authors
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Yang, L. ; Ju, Y.-Y. ; Medel, M.A. ; Fu, Y. ; Komber, H. ; Dmitrieva, E. ; Zhang, J.-J. ; Obermann, S. ; Campaña, A.G. ; Ma, J. ; Feng, X.
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Title
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Helical bilayer nonbenzenoid nanographene bearing a [10]helicene with two embedded heptagons
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Date
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06.01.2023
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Number
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60722
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Abstract
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The precision synthesis of helical bilayer nanographenes (NGs) with new topology is of substantial interest due to 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 tailed-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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Publisher
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Angewandte Chemie - International Edition
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Wikidata
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Citation
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Angewandte Chemie - International Edition 62 (2023) e202216193
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DOI
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https://doi.org/10.1002/ANIE.202216193
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Tags
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