Issue 14, 2019

Wave-shaped polycyclic hydrocarbons with controlled aromaticity

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.

Graphical abstract: Wave-shaped polycyclic hydrocarbons with controlled aromaticity

Supplementary files

Article information

Article type
Edge Article
Submitted
04 Dec. 2018
Accepted
27 Febr. 2019
First published
28 Febr. 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 4025-4031

Wave-shaped polycyclic hydrocarbons with controlled aromaticity

J. Ma, K. Zhang, K. S. Schellhammer, Y. Fu, H. Komber, C. Xu, A. A. Popov, F. Hennersdorf, J. J. Weigand, S. Zhou, W. Pisula, F. Ortmann, R. Berger, J. Liu and X. Feng, Chem. Sci., 2019, 10, 4025 DOI: 10.1039/C8SC05416A

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