Pressure-Induced Diels-Alder Reactions in C6H6-C6F6 Cocrystal towards Graphane Structure

Wang, Yajie; Dong, Xiao; Tang, Xingyu; Zheng, Haiyan; Li, Kuo; Lin, Xiaohuan; Fang, Leiming; Sun, Guang'ai; Chen, Xiping; Xie, Lei; Bull, Craig L.; Funnell, Nicholas P.; Hattori, Takanori; Sano-Furukawa, Asami; Chen, Jihua; Hensley, Dale K.; Cody, George D.; Ren, Yang; Lee, Hyun Hwi; Mao, Ho-kwang

doi:10.1002/anie.201813120

Title: Pressure-Induced Diels-Alder Reactions in C₆H₆-C₆F₆ Cocrystal towards Graphane Structure

Journal Article · 28 November 2018 · Angewandte Chemie (International Edition)

DOI: https://doi.org/10.1002/anie.201813120 · OSTI ID:1489507

^[1];

^[1]; Lin, Xiaohuan ^[1]; Fang, Leiming ^[2]; Sun, Guang'ai ^[2]; Chen, Xiping ^[2]; Xie, Lei ^[2];

^[3]; Funnell, Nicholas P. ^[3]; Hattori, Takanori ^[4]; Sano-Furukawa, Asami ^[4];

^[5];

^[5]; Cody, George D. ^[6]; Ren, Yang ^[7]; Lee, Hyun Hwi ^[8]; Mao, Ho-kwang ^[9]

Center for High Pressure Science and Technology Advanced Research, Beijing (China)
China Academy of Engineering Physics, Mianyang (China). Key Lab. of Neutron Physics and Inst. of Nuclear Physics and Chemistry
Science and Technology Facilities Council (STFC), Oxford (United Kingdom). Rutherford Appleton Lab., ISIS Neutron Source
Japan Atomic Energy Agency (JAEA), Tokai (Japan). J-PARC Center
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Science (CNMS)
Carnegie Inst. of Washington, Washington, DC (United States). Geophysical Lab.
Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Pohang Accelerator Lab. (PAL) (Korea, Republic of). POSTECH
Center for High Pressure Science and Technology Advanced Research, Beijing (China); Carnegie Inst. of Washington, Washington, DC (United States). Geophysical Lab.

Pressure-induced polymerization (PIP) of aromatics is a novel method to construct sp³-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. In conclusion, 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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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS); Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States). Spallation Neutron Source (SNS) and Center for Nanophase Materials Science (CNMS)

Sponsoring Organization:: National Natural Science Foundation of China (NNSFC); National Natural Science Foundation of China (NSFC); Science and Technology Facilities Council (STFC); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Scientific User Facilities Division

Grant/Contract Number:: AC02-06CH11357; AC05-00OR22725

OSTI ID:: 1489507

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Vol. 58; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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cycloaddition
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Title: Pressure-Induced Diels-Alder Reactions in C6H6-C6F6 Cocrystal towards Graphane Structure

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Title: Pressure-Induced Diels-Alder Reactions in C₆H₆-C₆F₆ Cocrystal towards Graphane Structure