Pressure-Induced Polymerization of Polycyclic Arene-Perfluoroarene Cocrystals: Single Crystal X-ray Diffraction Studies, Reaction Kinetics, and Design of Columnar Hydrofluorocarbons

被引:66
作者
Friedrich, Alexandra [6 ]
Collings, Ines E. [1 ]
Dziubek, Kamil F. [2 ]
Fanetti, Samuele [2 ,3 ]
Radacki, Krzysztof [6 ]
Ruiz-Fuertes, Javier [4 ,5 ]
Pellicer-Porres, Julio [4 ]
Hanfland, Michael [1 ]
Sieh, Daniel [6 ]
Bini, Roberto [2 ,3 ,7 ]
Clark, Stewart J. [8 ]
Marder, Todd B. [6 ]
机构
[1] European Synchrotron Radiat Facil, F-38000 Grenoble, France
[2] LENS, European Lab Nonlinear Spect, I-50019 Florence, Italy
[3] Natl Res Council Italy, Inst Chem OrganoMetall Cpds, ICCOM CNR, I-50019 Florence, Italy
[4] Univ Valencia, Dept Fis Aplicada ICMUV, MALTA Consolider Team, Burjassot 46100, Spain
[5] Univ Cantabria, MALTA Consolider Team, DCITIMAC, Santander 39005, Spain
[6] Julius Maximilians Univ Wurzburg, Inst Anorgan Chem, D-97074 Wurzburg, Germany
[7] Univ Firenze, Dipartimento Chim Ugo Schiff, I-50019 Florence, Italy
[8] Univ Durham, Dept Phys, Sci Labs, South Rd, Durham DH1 3LE, England
基金
英国工程与自然科学研究理事会; 欧盟地平线“2020”;
关键词
1/1; COMPLEXES; PHASE-BEHAVIOR; AROMATIC-HYDROCARBONS; STACKING INTERACTIONS; OPTICAL-PROPERTIES; CHEMICAL-REACTIONS; TRANS-STILBENE; BENZENE I; OCTAFLUORONAPHTHALENE; HEXAFLUOROBENZENE;
D O I
10.1021/jacs.0c09021
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pressure-induced polymerization of aromatic compounds leads to novel materials containing sp(3) carbon-bonded networks. The choice of the molecular species and the control of their arrangement in the crystal structures via intermolecular interactions, such as the arene-perfluoroarene interaction, can enable the design of target polymers. We have investigated the crystal structure compression and pressure-induced polymerization reaction kinetics of two polycyclic 1:1 arene-perfluoroarene cocrystals, naphthalene/octafluoronaphthalene (NOFN) and anthracene/octafluoronaphthalene (AOFN), up to 25 and 30 GPa, respectively, using single-crystal synchrotron X-ray diffraction, infrared spectroscopy, and theoretical computations based on density-functional theory. Our study shows the remarkable pressure stability of the parallel arene-perfluoroarene pi-stacking arrangement and a reduction of the interplanar pi-stacking separations by ca. 19-22% before the critical reaction distance is reached. A further strong, discontinuous, and irreversible reduction along the stacking direction at 20 GPa in NOFN (18.8%) and 25 GPa in AOFN (8.7%) indicates the pressure-induced breakdown of pi-stacking by formation of a-bonded polymers. The association of the structural distortion with the occurrence of a chemical reaction is confirmed by a high-pressure kinetic study using infrared spectroscopy, indicating one-dimensional polymer growth. Structural predictions for the fully polymerized high-pressure phases consisting of highly ordered rods of hydrofluorocarbons are presented based on theoretical computations, which are in excellent agreement with the experimentally determined unit-cell parameters. We show that the polymerization takes place along the arene-perfluoroarene pi-stacking direction and that the lateral extension of the columns depends on the extension of the arene and perfluoroarene molecules.
引用
收藏
页码:18907 / 18923
页数:17
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