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Journal Articles

Pressure-induced Diels-Alder reactions in C$$_{6}$$H$$_{6}$$ - C$$_{6}$$F$$_{6}$$ cocrystal towards graphane structure

Wang, Y.*; Dong, X.*; Tang, X.*; Zheng, H.*; Li, K.*; Lin, X.*; Fang, L.*; Sun, G.*; Chen, X.*; Xie, L.*; et al.

Angewandte Chemie; International Edition, 58(5), p.1468 - 1473, 2019/01

 Times Cited Count:29 Percentile:79.84(Chemistry, Multidisciplinary)

Pressure-induced polymerization (PIP) of aromatics is a novel method to construct sp$$^{3}$$-carbon frameworks, and nanothreads with diamond-like structures were synthesized by compressing benzene and its derivatives. Here by compressing benzene-hexafluorobenzene cocrystal(CHCF), we identified H-F-substituted graphane with a layered structure in the PIP product. Based on the crystal structure determined from the in situ neutron diffraction and the intermediate products identified by the gas chromatography-mass spectrum, we found that at 20 GPa CHCF forms tilted columns with benzene and hexafluorobenzene stacked alternatively, which leads to a [4+2] polymer, and then transfers to short-range ordered hydrogenated-fluorinated graphane. The reaction process contains [4+2] Diels-Alder, retro-Diels-Alder, and 1-1' coupling, and the former is the key reaction in the PIP. Our studies confirmed the elemental reactions of the CHCF for the first time, which provides a novel insight into the PIP of aromatics.

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