Wave-shaped polycyclic hydrocarbons with controlled aromaticity

Ma J, Zhang K, Schellhammer KS, Fu Y, Komber H, Xu C, Popov AA, Hennersdorf F, Weigand JJ, Zhou S, Pisula W, Ortmann F, Berger R, Liu J, Feng X (2019)

Publication Type: Journal article

Publication year: 2019

Journal

Chemical Science Royal Society of Chemistry

Book Volume: 10

Pages Range: 4025-4031

Journal Issue: 14

DOI: 10.1039/C8SC05416A

Abstract

Controlling the aromaticity and electronic properties of curved π-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 π-electrons. Among them, the wave-shaped π-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.

Involved external institutions

Technische Universität Dresden DE Germany (DE) Max-Planck-Institut für Polymerforschung (MPI-P) / Max Planck Institute for Polymer Research DE Germany (DE) Leibniz-Institut für Polymerforschung Dresden e. V. DE Germany (DE) Helmholtz-Zentrum Dresden-Rossendorf (HZDR) 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:

Ma, J., Zhang, K., Schellhammer, K.S., Fu, Y., Komber, H., Xu, C.,... Feng, X. (2019). Wave-shaped polycyclic hydrocarbons with controlled aromaticity. Chemical Science, 10(14), 4025-4031. https://doi.org/10.1039/C8SC05416A

MLA:

Ma, Ji, et al. "Wave-shaped polycyclic hydrocarbons with controlled aromaticity." Chemical Science 10.14 (2019): 4025-4031.

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