Journal Home > Volume 15 , Issue 5
Nano Research 2022, 15(5): 4606-4612 https://doi.org/10.1007/s12274-022-4215-8
Research Article | Issue | Published: 27 February 2022

Dehydro-Diels–Alder reaction and diamondization of bowl-shaped clusters C18Te3Br4(Bu-O)6

Show Author's Information Jinbo Zhang1,2,  Manli Ma1,  Rong Zhou1,  Hongqiang Chu1,  Xue Wang1,  Shaojie Wang2,  Huhu Tian3,4,  Zhipeng Yan5,  Mingtao Li6,  Zhongyan Wu7,  Bin Li7,  Jiafeng Yan7,  Lan Anh Thi Nguyen7,  Rongxing Cao1,  Guoqing Wu1,  Xianghua Zeng1,  Hao-Li Zhang3( ),  Jaeyong Kim7( ),  Lin Wang2( ),  Yongjun Tian2
College of Physical Science and Technology, Yangzhou University, Yangzhou 225002, China
Center for High Pressure Science (CHiPS), State Key Laboratory of Metastable Materials Science and Technology, Yanshan University, Qinhuangdao 066004, China
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
Baotou Research Institute of Rare Earths, Baotou 014000, China
Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen 518055, China
Center for High Pressure Science and Technology Advanced Research, Shanghai 201203, China
Department of Physics, and High Pressure Research Center, Hanyang University, Seoul 04763, Republic of Korea
Keywords:
high-pressure, polycyclic aromatic hydrocarbons, dehydro-Diels–Alder reaction, diamondization
Topics:
Nanoclusters
Cite this article:
Zhang J, Ma M, Zhou R, et al. Dehydro-Diels–Alder reaction and diamondization of bowl-shaped clusters C18Te3Br4(Bu-O)6. Nano Research, 2022, 15(5): 4606-4612. https://doi.org/10.1007/s12274-022-4215-8
Download citation
EndNote(RIS)
BibTeX

932

Views

110

Downloads

Citations

3

Crossref

3

WoS

3

Scopus

0

CSCD

Abstract Full text Electronic supplementary material About this article

Dehydro-Diels–Alder (DDA) reaction is a textbook reaction for preparing six-membered rings in solution but is scarcely seen in solid-state synthesis. In this work, using multiple characterization techniques, we demonstrate that the bowl-shaped clusters C18Te3Br4(Bu-O)6 might experience a DDA reaction at room temperature and high pressure between 5.5 and 7.4 GPa. Above 17.0 GPa, it is found that the bonding conversion from the intramolecular sp2 to the intermolecular sp3 occurred, in the form of pressure-induced diamondization. The recovered samples from 20.0 and 36.1 GPa showed incomplete reversibility, while the decompression-induced graphitization of glassy carbon was observed during decompression from 46.5 GPa. The electrochemical impedance spectroscopy results indicated that the transport properties changed from grain boundary dominant to grain dominant due to the DDA reaction and the grain boundary effect disappeared as the intermolecular sp3 bonding building-up and carrier transmission channel formation above 17.0 GPa. The results in this study open a new route to construct the crystalline carbon materials with different transport properties.


menu
Abstract
Full text
Outline
Electronic supplementary material
About this article

Dehydro-Diels–Alder reaction and diamondization of bowl-shaped clusters C18Te3Br4(Bu-O)6

Show Author's information Jinbo Zhang1,2, Manli Ma1, Rong Zhou1, Hongqiang Chu1, Xue Wang1, Shaojie Wang2, Huhu Tian3,4, Zhipeng Yan5, Mingtao Li6, Zhongyan Wu7, Bin Li7, Jiafeng Yan7, Lan Anh Thi Nguyen7, Rongxing Cao1, Guoqing Wu1, Xianghua Zeng1, Hao-Li Zhang3( ), Jaeyong Kim7( ), Lin Wang2( ), Yongjun Tian2
College of Physical Science and Technology, Yangzhou University, Yangzhou 225002, China
Center for High Pressure Science (CHiPS), State Key Laboratory of Metastable Materials Science and Technology, Yanshan University, Qinhuangdao 066004, China
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
Baotou Research Institute of Rare Earths, Baotou 014000, China
Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen 518055, China
Center for High Pressure Science and Technology Advanced Research, Shanghai 201203, China
Department of Physics, and High Pressure Research Center, Hanyang University, Seoul 04763, Republic of Korea

Abstract

Dehydro-Diels–Alder (DDA) reaction is a textbook reaction for preparing six-membered rings in solution but is scarcely seen in solid-state synthesis. In this work, using multiple characterization techniques, we demonstrate that the bowl-shaped clusters C18Te3Br4(Bu-O)6 might experience a DDA reaction at room temperature and high pressure between 5.5 and 7.4 GPa. Above 17.0 GPa, it is found that the bonding conversion from the intramolecular sp2 to the intermolecular sp3 occurred, in the form of pressure-induced diamondization. The recovered samples from 20.0 and 36.1 GPa showed incomplete reversibility, while the decompression-induced graphitization of glassy carbon was observed during decompression from 46.5 GPa. The electrochemical impedance spectroscopy results indicated that the transport properties changed from grain boundary dominant to grain dominant due to the DDA reaction and the grain boundary effect disappeared as the intermolecular sp3 bonding building-up and carrier transmission channel formation above 17.0 GPa. The results in this study open a new route to construct the crystalline carbon materials with different transport properties.

Keywords: high-pressure, polycyclic aromatic hydrocarbons, dehydro-Diels–Alder reaction, diamondization

References(72)

1

Wang, Z. R.; Yu, F.; Xie, J.; Zhao, J. F.; Zou, Y.; Wang, Z. P.; Zhang, Q. C. Insights into the control of optoelectronic properties in mixed-stacking charge-transfer complexes. Chem.—Eur. J. 2020, 26, 3578–3585.
DOI Google Scholar
2

Dong, H. L.; Zhu, H. F.; Meng, Q.; Gong, X.; Hu, W. P. Organic photoresponse materials and devices. Chem. Soc. Rev. 2012, 41, 1754–1808.
DOI Google Scholar
3

Sun, Y. G.; Wang, L.; Liu, Y. Z.; Ren, Y. Birnessite-type MnO2 nanosheets with layered structures under high pressure: Elimination of crystalline stacking faults and oriented laminar assembly. Small 2015, 11, 300–305.
DOI Google Scholar
4

Zhang, L. J.; Wang, Y. C.; Lv, J.; Ma, Y. M. Materials discovery at high pressures. Nat. Rev. Mater. 2017, 2, 17005.
DOI Google Scholar
5

Mao, H. K.; Chen, X. J.; Ding, Y.; Li, B.; Wang, L. Solids, liquids, and gases under high pressure. Rev. Mod. Phys. 2018, 90, 015007.
DOI Google Scholar
6

Ceppatelli, M.; Santoro, M.; Bini, R.; Schettino, V. High pressure reactivity of solid furan probed by infrared and Raman spectroscopy. J. Chem. Phys. 2003, 118, 1499–1506.
DOI Google Scholar
7

Sun, J. M.; Dong, X.; Wang, Y. J.; Li, K.; Zheng, H. Y.; Wang, L. J.; Cody, G. D.; Tulk, C. A.; Molaison, J. J.; Lin, X. H. et al. Pressure-induced polymerization of acetylene: Structure-directed stereoselectivity and a possible route to graphane. Angew. Chem., Int. Ed. 2017, 56, 6553–6557.
DOI Google Scholar
8

Zhao, X. M.; Zhong, G. H.; Zhang, J.; Huang, Q. W.; Goncharov, A. F.; Lin, H. Q.; Chen, X. J. Combined experimental and computational study of high-pressure behavior of triphenylene. Sci. Rep. 2016, 6, 25600.
DOI Google Scholar
9

Ray, P.; Gray, J. L.; Badding, J. V.; Lueking, A. D. High-pressure reactivity of triptycene probed by Raman spectroscopy. J. Phys. Chem. B 2016, 120, 11035–11042.
DOI Google Scholar
10

Ciabini, L.; Santoro, M.; Bini, R.; Schettino, V. High pressure reactivity of solid benzene probed by infrared spectroscopy. J. Chem. Phys. 2002, 116, 2928–2935.
DOI Google Scholar
11

Ke, F.; Chen, Y. B.; Yin, K. T.; Yan, J. J.; Zhang, H. Z.; Liu, Z. X.; Tse, J. S.; Wu, J. Q.; Mao, H. K.; Chen, B. Large bandgap of pressurized trilayer graphene. Proc. Natl. Acad. Sci. USA 2019, 116, 9186–9190.
DOI Google Scholar
12

Samanta, S.; Lee, M.; Kim, D. S.; Kim, J.; Wang, L. High-pressure triggered quantum tunneling tuning through classical percolation in a single nanowire of a binary composite. Nano Res. 2019, 12, 1333–1338.
DOI Google Scholar
13

Ciabini, L.; Santoro, M.; Gorelli, F. A.; Bini, R.; Schettino, V.; Raugei, S. Triggering dynamics of the high-pressure benzene amorphization. Nat. Mater. 2007, 6, 39–43.
DOI Google Scholar
14

Wang, Y. J.; Wang, L. J.; Zheng, H. Y.; Li, K.; Andrzejewski, M.; Hattori, T.; Sano-Furukawa, A.; Katrusiak, A.; Meng, Y. F.; Liao, F. H. et al. Phase transitions and polymerization of C6H6–C6F6 cocrystal under extreme conditions. J. Phys. Chem. C 2016, 120, 29510–29519.
DOI Google Scholar
15

Wang, Y. J.; Dong, X.; Tang, X. Y.; Zheng, H. Y.; Li, K.; Lin, X. H.; Fang, L. M.; Sun, G. A.; Chen, X. P.; Xie, L. et al. Pressure-induced Diels–Alder reactions in C6H6–C6F6 cocrystal towards graphane structure. Angew. Chem., Int. Ed. 2019, 58, 1468–1473.
DOI Google Scholar
16

Aust, R. B.; Bentley, W. H.; Drickamer, H. G. Behavior of fused-ring aromatic hydrocarbons at very high pressure. J. Chem. Phys. 1964, 41, 1856–1864.
DOI Google Scholar
17

Davydov, V. A.; Rakhmanina, A. V.; Agafonov, V.; Narymbetov, B.; Boudou, J. P.; Szwarc, H. Conversion of polycyclic aromatic hydrocarbons to graphite and diamond at high pressures. Carbon 2004, 42, 261–269.
DOI Google Scholar
18

Wang, L.; Liu, B. B.; Li, H.; Yang, W. G.; Ding, Y.; Sinogeikin, S. V.; Meng, Y.; Liu, Z. X.; Zeng, X. C.; Mao, W. L. Long-range ordered carbon clusters: A crystalline material with amorphous building blocks. Science 2012, 337, 825–828.
DOI Google Scholar
19

Li, B.; Zhang, J. B.; Yan, Z. P.; Feng, M. N.; Yu, Z. H.; Wang, L. Pressure-induced dimerization of C60 at room temperature as revealed by an in situ spectroscopy study using an infrared laser. Crystals 2020, 10, 182.
DOI Google Scholar
20

Pei, C. Y.; Feng, M. N.; Yang, Z. X.; Yao, M. G.; Yuan, Y.; Li, X.; Hu, B. W.; Shen, M.; Chen, B.; Sundqvist, B. et al. Quasi 3D polymerization in C60 bilayers in a fullerene solvate. Carbon 2017, 124, 499–505.
DOI Google Scholar
21

Wang, L.; Liu, B.; Liu, D.; Hou, Y.; Yao, M.; Zou, G.; Li, H.; Luo, C.; Li, Y.; Liu, J. High pressure studies of nano/sub-micrometer C70 rods. Chin. Phys. C: High Energy Phys. Nucl. Phys. 2005, 29, 112–115.
Google Scholar
22

Chen, J. Y.; Kim, M.; Yoo, C. S. High structural stability of single wall carbon nanotube under quasi-hydrostatic high pressures. Chem. Phys. Lett. 2009, 479, 91–94.
DOI Google Scholar
23

Iizumi, Y.; Liu, Z.; Suenaga, K.; Okada, S.; Higashibayashi, S.; Sakurai, H.; Okazaki, T. Molecular arrangements of corannulene and sumanene in single-walled carbon nanotubes. ChemNanoMat 2018, 4, 557–561.
DOI Google Scholar
24

Okazaki, T.; Iizumi, Y.; Okubo, S.; Kataura, H.; Liu, Z.; Suenaga, K.; Tahara, Y.; Yudasaka, M.; Okada, S.; Iijima, S. Coaxially stacked coronene columns inside single-walled carbon nanotubes. Angew. Chem., Int. Ed. 2011, 50, 4853–4857.
DOI Google Scholar
25

Alvarez, L.; Le Parc, R.; Jourdain, V.; Dennler, S.; Bantignies, J. L.; Sauvajol, J. L.; Rose, J. A.; Scott, L. T. Temperature dependence and pressure dependence of the vibrational properties of corannulene. Phys. Status Solidi (B) 2008, 245, 2261–2263.
DOI Google Scholar
26

Du, M. R.; Dong, J. J.; Zhang, Y.; Yang, X. G.; Li, Z. P.; Wang, M. C.; Liu, R.; Liu, B.; Zhou, Q. J.; Wei, T. et al. Vibrational properties and polymerization of corannulene under pressure, probed by Raman and infrared spectroscopies. J. Phys. Chem. C 2019, 123, 23674–23681.
DOI Google Scholar
27

Hanson, J. C.; Nordman, C. E. The crystal and molecular structure of corannulene, C20H10. Acta Cryst. B 1976, 32, 1147–1153.
DOI Google Scholar
28

Shang, Y. C.; Liu, Z. D.; Dong, J. J.; Yao, M. G.; Yang, Z. X.; Li, Q. J.; Zhai, C. G.; Shen, F. R.; Hou, X. Y.; Wang, L. et al. Ultrahard bulk amorphous carbon from collapsed fullerene. Nature 2021, 599, 599–604.
DOI Google Scholar
29

Tang, H.; Yuan, X. H.; Cheng, Y.; Fei, H. Z.; Liu, F. Y.; Liang, T.; Zeng, Z. D.; Ishii, T.; Wang, M. S.; Katsura, T. et al. Synthesis of paracrystalline diamond. Nature 2021, 599, 605–610.
DOI Google Scholar
30

Li, X. X.; Zhu, Y. T.; Shao, J. F.; Wang, B. L.; Zhang, S. X.; Shao, Y. L.; Jin, X. J.; Yao, X. J.; Fang, R.; Shao, X. F. Non-pyrolytic, large-scale synthesis of trichalcogenasumanene: A two-step approach. Angew. Chem., Int. Ed. 2014, 53, 535–538.
DOI Google Scholar
31

Wang, S. T.; Li, X. X.; Hou, X. Q.; Sun, Y. T.; Shao, X. F. Tritellurasumanene: Ultrasound assisted one-pot synthesis and extended valence adducts with bromine. Chem. Commun. 2016, 52, 14486–14489.
DOI Google Scholar
32

McCormick, T. M.; Jahnke, A. A.; Lough, A. J.; Seferos, D. S. Tellurophenes with delocalized π-systems and their extended valence adducts. J. Am. Chem. Soc. 2012, 134, 3542–3548.
DOI Google Scholar
33

Mao, H. K.; Xu, J.; Bell, P. M. Calibration of the ruby pressure gauge to 800 kbar under quasi-hydrostatic conditions. J. Geophys. Res.:Solid Earth 1986, 91, 4673–4676.
DOI Google Scholar
34

Rahman, S.; Saqib, H.; Zhang, J. B.; Errandonea, D.; Menéndez, C.; Cazorla, C.; Samanta, S.; Li, X. D.; Lu, J. L.; Wang, L. Pressure-induced structural and semiconductor-semiconductor transitions in Co0.5Mg0.5Cr2O4. Phys. Rev. B 2018, 97, 174102.
DOI Google Scholar
35

Prescher, C.; Prakapenka, V. B. DIOPTAS: A program for reduction of two-dimensional X-ray diffraction data and data exploration. High Press. Res. 2015, 35, 223–230.
DOI Google Scholar
36

Dischler, B.; Bubenzer, A.; Koidl, P. Bonding in hydrogenated hard carbon studied by optical spectroscopy. Solid State Commun. 1983, 48, 105–108.
DOI Google Scholar
37

Dischler, B; Bubenzer, A.; Koidl, P. Hard carbon coatings with low optical absorption. Appl. Phys. Lett. 1983, 42, 636–638.
DOI Google Scholar
38

Zhang, P. J.; Tang, X. Y.; Wang, Y. D.; Wang, X.; Gao, D. X.; Li, Y. P.; Zheng, H. Y.; Wang, Y. J.; Wang, X. X.; Fu, R. Q. et al. Distance-selected topochemical dehydro-Diels–Alder reaction of 1, 4-diphenylbutadiyne toward crystalline graphitic nanoribbons. J. Am. Chem. Soc. 2020, 142, 17662–17669.
DOI Google Scholar
39

Chanyshev, A. D.; Litasov, K. D.; Shatskiy, A. F.; Ohtani, E. In situ X-ray diffraction study of decomposition of polycyclic aromatic hydrocarbons at pressures of 7–15 GPa: Implication to fluids under the Earth’ s and planetary environments. Chem. Geol. 2015, 405, 39–47.
DOI Google Scholar
40

Kvashnin, A. G.; Chernozatonskii, L. A.; Yakobson, B. I.; Sorokin, P. B. Phase diagram of quasi-two-dimensional carbon, from graphene to diamond. Nano Lett. 2014, 14, 676–681.
DOI Google Scholar
41

Mimura, K.; Toyama, S.; Sugitani, K. Shock-induced dehydrogenation of polycyclic aromatic hydrocarbons with or without serpentine: Implications for planetary accretion. Earth Planet. Sci. Lett. 2005, 232, 143–156.
DOI Google Scholar
42

Sun, B.; Dreger, Z. A.; Gupta, Y. M. High-pressure effects in pyrene crystals: Vibrational spectroscopy. J. Phys. Chem. A 2008, 112, 10546–10551.
DOI Google Scholar
43

Schindler, T. L.; Vohra, Y. K. A micro-Raman investigation of high-pressure quenched graphite. J. Phys.:Condens. Matter 1996, 8, 3963.
DOI Google Scholar
44

Ferrari, A. C.; Robertson, J. Interpretation of Raman spectra of disordered and amorphous carbon. Phys. Rev. B 2000, 61, 14095–14107.
DOI Google Scholar
45

Goncharov, A. F.; Makarenko, I. N.; Stishov, S. M. Graphite at pressures up to 55 GPa: Optical properties and Raman scattering-amorphous carbon. Sov. Phys. JETP 1989, 69, 380–381.
Google Scholar
46

Wang, Y. J.; Panzik, J. E.; Kiefer, B.; Lee, K. K. M. Crystal structure of graphite under room-temperature compression and decompression. Sci. Rep. 2012, 2, 520.
DOI Google Scholar
47

Yao, M. G.; Xiao, J. P.; Fan, X. H.; Liu, R.; Liu, B. B. Transparent, superhard amorphous carbon phase from compressing glassy carbon. Appl. Phys. Lett. 2014, 104, 021916.
DOI Google Scholar
48

Barboza, A. P. M.; Guimaraes, M. H. D.; Massote, D. V. P.; Campos, L. C.; Neto, N. M. B.; Cancado, L. G.; Lacerda, R. G.; Chacham, H.; Mazzoni, M. S. C.; Neves, B. R. A. Room-temperature compression-induced diamondization of few-layer graphene. Adv. Mater. 2011, 23, 3014–3017.
DOI Google Scholar
49

Shiell, T. B.; McCulloch, D. G.; McKenzie, D. R.; Field, M. R.; Haberl, B.; Boehler, R.; Cook, B. A.; de Tomas, C.; Suarez-Martinez, I.; Marks, N. A. et al. Graphitization of glassy carbon after compression at room temperature. Phys. Rev. Lett. 2018, 120, 215701.
DOI Google Scholar
50

Lim, J.; Yoo, C. S. Intercalation of solid hydrogen into graphite under pressures. Appl. Phys. Lett. 2016, 109, 051905.
DOI Google Scholar
51

Lin, Y.; Zhang, L.; Mao, H. K.; Chow, P.; Xiao, Y. M.; Baldini, M.; Shu, J. F.; Mao, W. L. Amorphous diamond: A high-pressure superhard carbon allotrope. Phys. Rev. Lett. 2011, 107, 175504.
DOI Google Scholar
52

Clark, S. M.; Jeon, K. J.; Chen, J. Y.; Yoo, C. S. Few-layer graphene under high pressure: Raman and X-ray diffraction studies. Solid State Commun. 2013, 154, 15–18.
DOI Google Scholar
53

Garbarczyk, J. E.; Wasiucionek, M.; Machowski, P.; Jakubowski, W. Transition from ionic to electronic conduction in silver–vanadate–phosphate glasses. Solid State Ion. 1999, 119, 9–14.
DOI Google Scholar
54

Tuller, H. L. Ionic conduction in nanocrystalline materials. Solid State Ion. 2000, 131, 143–157.
DOI Google Scholar
55

Miller, E. D.; Nesting, D. C.; Badding, J. V. Quenchable transparent phase of carbon. Chem. Mater. 1997, 9, 18–22.
DOI Google Scholar
56

Wu, J. H.; Wang, S. Y.; Lei, Z. W.; Guan, R. N.; Chen, M. Q.; Du, P. W.; Lu, Y. L.; Cao, R. G.; Yang, S. F. Pomegranate-like C60@cobalt/nitrogen-codoped porous carbon for high-performance oxygen reduction reaction and lithium-sulfur battery. Nano Res. 2021, 14, 2596–2605.
DOI Google Scholar
57

Soler-Piña, F. J.; Hernández-Rentero, C.; Caballero, A.; Morales, J.; Canales-Vázquez, J. Highly graphitized carbon nanosheets with embedded Ni nanocrystals as anode for Li-ion batteries. Nano Res. 2020, 13, 86–94.
DOI Google Scholar
58

Li, G. C.; Yin, Z. L.; Dai, Y. Q.; You, B. Z.; Guo, H. J.; Wang, Z. X.; Yan, G. C.; Liu, Y.; Wang, J. X. Graphitic nanorings for super-long lifespan lithium-ion capacitors. Nano Res. 2020, 13, 2909–2916.
DOI Google Scholar
59

Li, H. Y.; Zhang, L. H.; Li, L.; Wu, C. W.; Huo, Y. J.; Chen, Y.; Liu, X. J.; Ke, X. X.; Luo, J.; Van Tendeloo, G. Two-in-one solution using insect wings to produce graphene–graphite films for efficient electrocatalysis. Nano Res. 2019, 12, 33–39.
DOI Google Scholar
60

Zhao, X. W.; Wu, Y. Z.; Wang, Y. S.; Wu, H. S.; Yang, Y. W.; Wang, Z. P.; Dai, L. X.; Shang, Y. Y.; Cao, A. Y. High-performance Li-ion batteries based on graphene quantum dot wrapped carbon nanotube hybrid anodes. Nano Res. 2020, 13, 1044–1052.
DOI Google Scholar
61

Mao, W. L.; Mao, H. K.; Eng, P. J.; Trainor, T. P.; Newville, M.; Kao, C. C.; Heinz, D. L.; Shu, J. F.; Meng, Y.; Hemley, R. J. Bonding changes in compressed superhard graphite. Science 2003, 302, 425–427.
DOI Google Scholar
62

Harris, P. J. F. Fullerene-related structure of commercial glassy carbons. Philos. Mag. 2004, 84, 3159–3167.
DOI Google Scholar
63

Townsend, S. J.; Lenosky, T. J.; Muller, D. A.; Nichols, C. S.; Elser, V. Negatively curved graphitic sheet model of amorphous carbon. Phys. Rev. Lett. 1992, 69, 921–924.
DOI Google Scholar
64

Martin, J. W.; Slavchov, R. I.; Yapp, E. K. Y.; Akroyd, J.; Mosbach, S.; Kraft, M. The polarization of polycyclic aromatic hydrocarbons curved by pentagon incorporation: The role of the flexoelectric dipole. J. Phys. Chem. C 2017, 121, 27154–27163.
DOI Google Scholar
65

Wentorf, R. H. Jr. The behavior of some carbonaceous materials at very high pressures and high temperatures. J. Phys. Chem. 1965, 69, 3063–3069.
DOI Google Scholar
66

Compagnini, G.; Calcagno, L.; Foti, G. Hydrogen effect on atomic configuration of keV-ion-irradiated carbon. Phys. Rev. Lett. 1992, 69, 454–457.
DOI Google Scholar
67

Martins, L. G. P.; Matos, M. J. S.; Paschoal, A. R.; Freire, P. T. C.; Andrade, N. F.; Aguiar, A. L.; Kong, J.; Neves, B. R. A.; de Oliveira, A. B.; Mazzoni, M. S. C. et al. Raman evidence for pressure-induced formation of diamondene. Nat. Commun. 2017, 8, 96.
DOI Google Scholar
68

Gao, Y.; Ma, Y. Z.; An, Q.; Levitas, V.; Zhang, Y. Y.; Feng, B.; Chaudhuri, J.; Goddard III, W. A. Shear driven formation of nano-diamonds at sub-gigapascals and 300 K. Carbon 2019, 146, 364–368.
DOI Google Scholar
69

Dong, J. J.; Yao, Z.; Yao, M. G.; Li, R.; Hu, K.; Zhu, L. Y.; Wang, Y.; Sun, H. H.; Sundqvist, B.; Yang, K. et al. Decompression-induced diamond formation from graphite sheared under pressure. Phys. Rev. Lett. 2020, 124, 065701.
DOI Google Scholar
70

Solopova, N. A.; Dubrovinskaia, N.; Dubrovinsky, L. Raman spectroscopy of glassy carbon up to 60 GPa. Appl. Phys. Lett. 2013, 102, 121909.
DOI Google Scholar
71

Jackson, B. R.; Trout, C. C.; Badding, J. V. UV Raman analysis of the C: H network formed by compression of benzene. Chem. Mater. 2003, 15, 1820–1824.
DOI Google Scholar
72

Fujikawa, T.; Preda, D. V.; Segawa, Y.; Itami, K.; Scott, L. T. Corannulene-helicene hybrids: Chiral π-systems comprising both bowl and helical motifs. Org. Lett. 2016, 18, 3992–3995.
DOI Google Scholar
File
12274_2022_4215_MOESM1_ESM.pdf (282.8 KB)
Publication history
Copyright
Acknowledgements

Publication history

Received: 29 December 2021
Revised: 05 February 2022
Accepted: 07 February 2022
Published: 27 February 2022
Issue date: May 2022

Copyright

© Tsinghua University Press 2022

Acknowledgements

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Nos. 52090020 and 11874076) and the National Research Foundation of Korea (Nos. 2016K1A4A3914691 and 2018R1DA1B070498).

Return