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Title Helical nanographenes containing an azulene unit: Synthesis, crystal structures, and properties
Date 22.12.2019
Number 57165
Abstract Three unprecedented helical nanographenes (1, 2, and 3) containing an azulene unit are synthesized. The resultant helical structures are unambiguously confirmed by X–ray crystallographic analysis. The embedded azulene unit in 2 possesses a record–high twisting degree (16.1°) as a result of the contiguous steric repulsion at the helical inner rim. Structural analysis in combination with theoretical calculations reveals that these helical nanographenes manifest a global aromatic structure, while the inner azulene unit exhibits weak antiaromatic character. Furthermore, UV/Vis–spectral measurements reveal that superhelicenes 2 and 3 possess narrow energy gaps (2: 1.88 eV; 3: 2.03 eV), as corroborated by cyclic voltammetry and supported by density functional theory (DFT) calculations. The stable oxidized and reduced states of 2 and 3 are characterized by in–situ EPR/Vis–NIR spectroelectrochemistry. Our study provides a novel synthetic strategy for helical nanographenes containing azulene units as well as their associated structures and physical properties.
URL https://doi.org/10.1002/ANGE.201914716
Publisher Angewandte Chemie
Identifier
Citation Angewandte Chemie (2019) Early view
DOI https://doi.org/10.1002/ANGE.201914716
Authors Ma, J. ; Fu, Y. ; Dmitrieva, E. ; Liu, F. ; Komber, H. ; Hennersdorf, F. ; Popov, A. A. ; Weigand, J. J. ; Liu, J. ; Feng, X.
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