Helical Bilayer Nonbenzenoid Nanographene Bearing a [10]Helicene with Two Embedded Heptagons

Yang L, Ju YY, Medel MAA, Fu Y, Komber H, Dmitrieva E, Zhang JJ, Obermann S, Campana AGG, Ma J, Feng X (2023)

Publication Type: Journal article

Publication year: 2023

Journal

Angewandte Chemie International Edition Wiley

Book Volume: 62

Article Number: e202216193

Journal Issue: 4

DOI: 10.1002/anie.202216193

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.

Involved external institutions

Technische Universität Dresden DE Germany (DE) Xiamen University CN China (CN) Universidad de Granada ES Spain (ES) Leibniz-Institut für Polymerforschung Dresden e. V. DE Germany (DE) Leibniz-Institut für Festkörper- und Werkstoffforschung Dresden e.V. (IFW) / Leibniz Institute for Solid State and Materials Research Dresden DE Germany (DE)

How to cite

APA:

Yang, L., Ju, Y.-Y., Medel, M.A.A., Fu, Y., Komber, H., Dmitrieva, E.,... Feng, X. (2023). Helical Bilayer Nonbenzenoid Nanographene Bearing a [10]Helicene with Two Embedded Heptagons. Angewandte Chemie International Edition, 62(4). https://doi.org/10.1002/anie.202216193

MLA:

Yang, Lin, et al. "Helical Bilayer Nonbenzenoid Nanographene Bearing a [10]Helicene with Two Embedded Heptagons." Angewandte Chemie International Edition 62.4 (2023).

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