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Authors Ma, J. ; Schellhammer, K. S. ; Fu, Y. ; Komber, H. ; Xu, C. ; Popov, A. A. ; Hennersdorf, F. ; Weigand, J. J. ; Zhou, S. ; Pisula, W. ; Ortmann, F. ; Berger, R. ; Liu, J. ; Feng, X.
Title Wave-shaped polycyclic hydrocarbons with controlled aromaticity
Date 13.05.2019
Number 55285
Abstract Controlling the aromaticity and electronic properties of curved p-conjugated systems has been increasingly attractive for the development of novel functional materials for organic electronics. Herein, we demonstrate an efficient synthesis of two novel wave-shaped polycyclic hydrocarbons (PHs) 1 and 2 with 64 p-electrons. Among them, the wave-shaped p-conjugated carbon skeleton of 2 is unambiguously revealed by single-crystal X-ray crystallography analysis. The wave-shaped geometry is induced by steric congestion in the cove and fjord regions. Remarkably, the aromaticity of these two structural isomers can be tailored by the annulated direction of cyclopenta[b]fluorene units. Isomer 1 (Eoptg = 1.13 eV) behaves as a closed-shell compound with weakly antiaromatic feature, whereas its structural isomer 2 displays a highly stable tetraradical character (y0 = 0.23; y1 = 0.22; t1/2 = 91 days) with a narrow optical energy gap of 0.96 eV. Moreover, the curved PH 2 exhibits remarkable ambipolar charge transport in solution-processed organic thin-film transistors. Our research provides a new insight into the design and synthesis of stable functional curved aromatics with multiradical characters.
Publisher Chemical Science
Wikidata
Citation Chemical Science 10 (2019) 4025-4031
DOI https://doi.org/10.1039/C8SC05416A
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