najoNanosystems: Physics, Chemistry, MathematicsНаносистемы: физика, химия, математика2220-80542305-7971Университет ИТМО10.17586/2220-8054-2016-7-1-44-50najo-756Research ArticlePAPERS, PRESENTED AT THE CONFERENCEPAPERS, PRESENTED AT THE CONFERENCEIs graphane the most stable carbon monohydride?Is graphane the most stable carbon monohydride?KondrinM. V.KondrinM. V.

142190 Troitsk, Moscow

142190 Troitsk, Moscow

mkondrin@hppi.troitsk.ruBrazhkinV. V.BrazhkinV. V.

142190 Troitsk, Moscow

142190 Troitsk, Moscow

Institute for High Pressure Physics RASInstitute for High Pressure Physics RAS20161408202571Special Issue: Proceedings of the 12th Biennial International Conference “Advanced Carbon Nanostructures” (ACNS’2015)4450Copyright © Kondrin M.V., Brazhkin V.V., 20252025Kondrin M.V., Brazhkin V.V.Kondrin M.V., Brazhkin V.V.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://nanojournal.ifmo.ru/jour/article/view/756

We discuss a number of hydrocarbon structures whose cohesive energy is not worse than that of benzene and graphanes. These structures can be regarded as sublattices of known carbon structures so the strain exerted on the crystal lattice is minimal and caused mostly by the steric interactions of hydrogen atoms. Possible synthetic routes are proposed. Due to their exceptional mechanical, structural and electrical properties, these crystal structures may have utility as mechanical, optoelectronic or biological materials.

We discuss a number of hydrocarbon structures whose cohesive energy is not worse than that of benzene and graphanes. These structures can be regarded as sublattices of known carbon structures so the strain exerted on the crystal lattice is minimal and caused mostly by the steric interactions of hydrogen atoms. Possible synthetic routes are proposed. Due to their exceptional mechanical, structural and electrical properties, these crystal structures may have utility as mechanical, optoelectronic or biological materials.

graphanediamond monohydridehydrocarbonsnitrogenhigh pressuresgraphanediamond monohydridehydrocarbonsnitrogenhigh pressuresThe authors acknowledge financial support from the RSF (Grant No. 14-22-00093) and thank Y.B. Lebed for assistance and helpful discussions.ReferencesSluiter M. H. F., Kawazoe Y. Cluster expansion method for adsorption: Application to hydrogen chemisorption on graphene. Phys. Rev. B, 2003, 68 (8), P. 085410.Sluiter M. H. F., Kawazoe Y. Cluster expansion method for adsorption: Application to hydrogen chemisorption on graphene. Phys. Rev. B, 2003, 68 (8), P. 085410.Sofo J., Chaudhari A., Barber G. Graphane: A two-dimensional hydrocarbon. Phys. Rev. B, 2007, 75 (15), P. 153401.Sofo J., Chaudhari A., Barber G. Graphane: A two-dimensional hydrocarbon. Phys. Rev. B, 2007, 75 (15), P. 153401.Elias D. C., Nair R. R., Mohiuddin T. M. G., Morozov S. V., Blake P., Halsall M. P., Ferrari A. C., Boukhvalov D. W., Katsnelson M. I., Geim A. K., Novoselov K. S. Control of Graphene’s Properties by Reversible Hydrogenation: Evidence for Graphane. Science, 2009, 323 (5914), P. 610–613.Elias D. C., Nair R. R., Mohiuddin T. M. G., Morozov S. V., Blake P., Halsall M. P., Ferrari A. C., Boukhvalov D. W., Katsnelson M. I., Geim A. K., Novoselov K. S. Control of Graphene’s Properties by Reversible Hydrogenation: Evidence for Graphane. Science, 2009, 323 (5914), P. 610–613.Savini G., Ferrari A. C., Giustino F. First-Principles Prediction of Doped Graphane as a High-Temperature Electron-Phonon Superconductor. Phys. Rev. Lett., 2010, 105 (3), P. 037002.Savini G., Ferrari A. C., Giustino F. First-Principles Prediction of Doped Graphane as a High-Temperature Electron-Phonon Superconductor. Phys. Rev. Lett., 2010, 105 (3), P. 037002.Loktev V., Turkowski V. Possible High-Temperature Superconductivity in Multilayer Graphane: Can the Cuprates be Beaten? Journal of Low Temperature Physics, 2011, 164 (5-6), P. 264–271.Loktev V., Turkowski V. Possible High-Temperature Superconductivity in Multilayer Graphane: Can the Cuprates be Beaten? Journal of Low Temperature Physics, 2011, 164 (5-6), P. 264–271.Peng Q., Dearden A. K., Crean J., Han L., Liu S., Wen X., De S. New materials graphyne, graphdiyne, graphone, and graphane: review of properties, synthesis, and application in nanotechnology. Nanotechnology, Science and Applications, 2104, 7, P. 1–29.Peng Q., Dearden A. K., Crean J., Han L., Liu S., Wen X., De S. New materials graphyne, graphdiyne, graphone, and graphane: review of properties, synthesis, and application in nanotechnology. Nanotechnology, Science and Applications, 2104, 7, P. 1–29.Zhou C., Chen S., Lou J., Wang J., Yang Q., Liu C., Huang D., Zhu T. Graphene’s cousin: the present and future of graphane. Nanoscale Research Letters, 2014, 9 (1), P. 26.Zhou C., Chen S., Lou J., Wang J., Yang Q., Liu C., Huang D., Zhu T. Graphene’s cousin: the present and future of graphane. Nanoscale Research Letters, 2014, 9 (1), P. 26.Ciabini L., Gorelli F. A., Santoro M., Bini R., Schettino V., Mezouar M. High-pressure and high-temperature equation of state and phase diagram of solid benzene. Phys. Rev. B, 2005, 72 (9), P. 094108.Ciabini L., Gorelli F. A., Santoro M., Bini R., Schettino V., Mezouar M. High-pressure and high-temperature equation of state and phase diagram of solid benzene. Phys. Rev. B, 2005, 72 (9), P. 094108.Eaton P. E., Cole T. W. Cubane. Journal of the American Chemical Society, 1964, 86 (15), P. 3157–3158.Eaton P. E., Cole T. W. Cubane. Journal of the American Chemical Society, 1964, 86 (15), P. 3157–3158.Fleischer E. B. X-Ray Structure Determination of Cubane. Journal of the American Chemical Society, 1964, 86 (18), P. 3889–3890.Fleischer E. B. X-Ray Structure Determination of Cubane. Journal of the American Chemical Society, 1964, 86 (18), P. 3889–3890.Yildirim T., Gehring P., Neumann D., Eaton P., Emrick T. Unusual structure, phase transition, and dynamics of solid cubane. Phys. Rev. Lett., 1997, 78 (26), P. 4938–4941.Yildirim T., Gehring P., Neumann D., Eaton P., Emrick T. Unusual structure, phase transition, and dynamics of solid cubane. Phys. Rev. Lett., 1997, 78 (26), P. 4938–4941.Criegee R., Askani R. Octamethylsemibullvalene. Angewandte Chemie International Edition in English, 1968, 7 (7), P. 537–537.Criegee R., Askani R. Octamethylsemibullvalene. Angewandte Chemie International Edition in English, 1968, 7 (7), P. 537–537.Wen X.-D., Hoffmann R., Ashcroft N. W. Benzene under High Pressure: a Story of Molecular Crystals Transforming to Saturated Networks, with a Possible Intermediate Metallic Phase. Journal of the American Chemical Society, 2011, 133 (23), P. 9023–9035.Wen X.-D., Hoffmann R., Ashcroft N. W. Benzene under High Pressure: a Story of Molecular Crystals Transforming to Saturated Networks, with a Possible Intermediate Metallic Phase. Journal of the American Chemical Society, 2011, 133 (23), P. 9023–9035.Fitzgibbons T. C., Guthrie M., shi Xu E., Crespi V. H., Davidowski S. K., Cody G. D., Alem N., Badding J. V. Benzene-derived carbon nanothreads. Nature Materials, 2015, 14, P. 43–47.Fitzgibbons T. C., Guthrie M., shi Xu E., Crespi V. H., Davidowski S. K., Cody G. D., Alem N., Badding J. V. Benzene-derived carbon nanothreads. Nature Materials, 2015, 14, P. 43–47.Lian C.-S., Wang X.-Q., Wang J.-T. Hydrogenated K4 carbon: A new stable cubic gauche structure of carbon hydride. The Journal of Chemical Physics, 2013, 138 (2), P. 024702.Lian C.-S., Wang X.-Q., Wang J.-T. Hydrogenated K4 carbon: A new stable cubic gauche structure of carbon hydride. The Journal of Chemical Physics, 2013, 138 (2), P. 024702.He C., Sun L. Z., Zhang C. X., Zhong J. Low energy three-dimensional hydrocarbon crystal from cold compression of benzene. Journal of Physics: Condensed Matter, 2013, 25 (20), P. 205403.He C., Sun L. Z., Zhang C. X., Zhong J. Low energy three-dimensional hydrocarbon crystal from cold compression of benzene. Journal of Physics: Condensed Matter, 2013, 25 (20), P. 205403.Lian C.-S., Li H.-D., Wang J.-T. Crystalline structures of polymeric hydrocarbon with 3,4-fold helical chains. Sci. Rep., 2015, 5, P. 07723.Lian C.-S., Li H.-D., Wang J.-T. Crystalline structures of polymeric hydrocarbon with 3,4-fold helical chains. Sci. Rep., 2015, 5, P. 07723.Eremets M. I., Gavriliuk A. G., Trojan I. A., Dzivenko D. A., Boehler R. Single-bonded cubic form of nitrogen. Nat Mater, 2004, 3 (8), P. 558–563.Eremets M. I., Gavriliuk A. G., Trojan I. A., Dzivenko D. A., Boehler R. Single-bonded cubic form of nitrogen. Nat Mater, 2004, 3 (8), P. 558–563.Wen X.-D., Hand L., Labet V., Yang T., Hoffmann R., Ashcroft N. W., Oganov A. R., Lyakhov A. O. Graphane sheets and crystals under pressure. Proceedings of the National Academy of Sciences, 2011, 108 (17), P. 6833– 6837.Wen X.-D., Hand L., Labet V., Yang T., Hoffmann R., Ashcroft N. W., Oganov A. R., Lyakhov A. O. Graphane sheets and crystals under pressure. Proceedings of the National Academy of Sciences, 2011, 108 (17), P. 6833– 6837.Kondrin M. V., Brazhkin V. V. Diamond monohydride: the most stable three-dimensional hydrocarbon. Phys. Chem. Chem. Phys., 2015, 17 (27), P. 17739–17744.Kondrin M. V., Brazhkin V. V. Diamond monohydride: the most stable three-dimensional hydrocarbon. Phys. Chem. Chem. Phys., 2015, 17 (27), P. 17739–17744.Blatov V. A., Proserpio D. M. Periodic-graph approaches in crystal structure prediction. In Modern Methods of Crystal Structure Prediction (Oganov A. R., editor), chapter 1, pp. 1–28. Wiley-VCH Verlag GmbH & Co. KGaA, 2010.Blatov V. A., Proserpio D. M. Periodic-graph approaches in crystal structure prediction. In Modern Methods of Crystal Structure Prediction (Oganov A. R., editor), chapter 1, pp. 1–28. Wiley-VCH Verlag GmbH & Co. KGaA, 2010.Delgado-Friedrichs O., Foster M. D., O’Keeffe M., Proserpio D. M., Treacy M. M. J., Yaghi O. M. What do we know about three-periodic nets? Journal of Solid State Chemistry, 2005, 178 (8), P. 2533 – 2554.Delgado-Friedrichs O., Foster M. D., O’Keeffe M., Proserpio D. M., Treacy M. M. J., Yaghi O. M. What do we know about three-periodic nets? Journal of Solid State Chemistry, 2005, 178 (8), P. 2533 – 2554.Németh P., Garvie L. A. J., Aoki T., Dubrovinskaia N., Dubrovinsky L., Buseck P. R. Lonsdaleite is faulted and twinned cubic diamond and does not exist as a discrete material. Nat Commun, 2014, 5.Németh P., Garvie L. A. J., Aoki T., Dubrovinskaia N., Dubrovinsky L., Buseck P. R. Lonsdaleite is faulted and twinned cubic diamond and does not exist as a discrete material. Nat Commun, 2014, 5.Tolèdano P., Dmitriev V. Reconstructive phase transitions in crystals and quasicrystals. World Scientific, Singapore, 1996.Tolèdano P., Dmitriev V. Reconstructive phase transitions in crystals and quasicrystals. World Scientific, Singapore, 1996.Aroyo M. I., Perez-Mato J. M., Capillas C., Kroumova E., Ivantchev S., Madariaga G., Kirov A., Wondratschek H. Bilbao Crystallographic Server: I. Databases and crystallographic computing programs. Zeitschrift fu¨r Kristallographie, 2006, 221 (1), P. 15–27.Aroyo M. I., Perez-Mato J. M., Capillas C., Kroumova E., Ivantchev S., Madariaga G., Kirov A., Wondratschek H. Bilbao Crystallographic Server: I. Databases and crystallographic computing programs. Zeitschrift fu¨r Kristallographie, 2006, 221 (1), P. 15–27.Capillas C., Kroumova E., Aroyo M. I., Perez-Mato J. M., Stokes H. T., Hatch D. M. SYMMODES: a software package for group-theoretical analysis of structural phase transitions. Journal of Applied Crystallography, 2003, 36 (3 Part 2), P. 953–954.Capillas C., Kroumova E., Aroyo M. I., Perez-Mato J. M., Stokes H. T., Hatch D. M. SYMMODES: a software package for group-theoretical analysis of structural phase transitions. Journal of Applied Crystallography, 2003, 36 (3 Part 2), P. 953–954.Kroumova E., Perez-Mato J. M., Aroyo M. I. WYCKSPLIT: a computer program for determination of the relations of Wyckoff positions for a group-subgroup pair. J. Appl. Cryst., 1998, 31, P. 646.Kroumova E., Perez-Mato J. M., Aroyo M. I. WYCKSPLIT: a computer program for determination of the relations of Wyckoff positions for a group-subgroup pair. J. Appl. Cryst., 1998, 31, P. 646.Jmol: an open-source Java viewer for chemical structures in 3D. http://www.jmol.org/.Jmol: an open-source Java viewer for chemical structures in 3D. http://www.jmol.org/.Artyukhov V. I., Chernozatonskii L. A. Structure and Layer Interaction in Carbon Monofluoride and Graphane: A Comparative Computational Study. The Journal of Physical Chemistry A, 2010, 114 (16), P. 5389–5396.Artyukhov V. I., Chernozatonskii L. A. Structure and Layer Interaction in Carbon Monofluoride and Graphane: A Comparative Computational Study. The Journal of Physical Chemistry A, 2010, 114 (16), P. 5389–5396.Giannozzi P., Baroni S., et al . QUANTUM ESPRESSO: a modular and open-source software project for quantum simulations of materials. Journal of Physics: Condensed Matter, 2009, 21 (39), P. 395502.Giannozzi P., Baroni S., et al . QUANTUM ESPRESSO: a modular and open-source software project for quantum simulations of materials. Journal of Physics: Condensed Matter, 2009, 21 (39), P. 395502.Balaban A. T., Klein D. J., Seitz W. A. Holes in diamond or carbon nitride lattices. International Journal of Quantum Chemistry, 1996, 60 (5), P. 1065–1068.Balaban A. T., Klein D. J., Seitz W. A. Holes in diamond or carbon nitride lattices. International Journal of Quantum Chemistry, 1996, 60 (5), P. 1065–1068.Clay W. A., Dahl J. E. P., Carlson R. M. K., Melosh N. A., Shen Z.-X. Physical properties of materials derived from diamondoid molecules. Reports on Progress in Physics, 2015, 78 (1), P. 016501.Clay W. A., Dahl J. E. P., Carlson R. M. K., Melosh N. A., Shen Z.-X. Physical properties of materials derived from diamondoid molecules. Reports on Progress in Physics, 2015, 78 (1), P. 016501.Garcia J. C., Assali L. V. C., Machado W. V. M., Justo J. F. Crystal engineering using functionalized adamantane. Journal of Physics: Condensed Matter, 2010, 22 (31), P. 315303.Garcia J. C., Assali L. V. C., Machado W. V. M., Justo J. F. Crystal engineering using functionalized adamantane. Journal of Physics: Condensed Matter, 2010, 22 (31), P. 315303.Garcia J. C., Justo J. F., Machado W. V. M., Assali L. V. C. Functionalized adamantane: Building blocks for nanostructure self-assembly. Phys. Rev. B, 2009, 80 (12), P. 125421.Garcia J. C., Justo J. F., Machado W. V. M., Assali L. V. C. Functionalized adamantane: Building blocks for nanostructure self-assembly. Phys. Rev. B, 2009, 80 (12), P. 125421.Mujica A., Rubio A., Muñoz A., Needs R. J. High-pressure phases of group-IV, III-V, and II-VI compounds. Rev. Mod. Phys., 2003, 75 (3), P. 863–912.Mujica A., Rubio A., Muñoz A., Needs R. J. High-pressure phases of group-IV, III-V, and II-VI compounds. Rev. Mod. Phys., 2003, 75 (3), P. 863–912.Johnston R. L., Hoffmann R. Superdense carbon, C8: supercubane or analog of γ-silicon? Journal of the American Chemical Society, 1989, 111 (3), P. 810–819.Johnston R. L., Hoffmann R. Superdense carbon, C8: supercubane or analog of γ-silicon? Journal of the American Chemical Society, 1989, 111 (3), P. 810–819.Correa A. A., Bonev S. A., Galli G. Carbon under extreme conditions: Phase boundaries and electronic properties from first-principles theory. Proceedings of the National Academy of Sciences, 2006, 103 (5), P. 1204–1208.Correa A. A., Bonev S. A., Galli G. Carbon under extreme conditions: Phase boundaries and electronic properties from first-principles theory. Proceedings of the National Academy of Sciences, 2006, 103 (5), P. 1204–1208.Mailhiot C., Yang L. H., McMahan A. K. Polymeric nitrogen. Phys. Rev. B, 1992, 46 (22), P. 14419–14435.Mailhiot C., Yang L. H., McMahan A. K. Polymeric nitrogen. Phys. Rev. B, 1992, 46 (22), P. 14419–14435.Brazhkin V. V. Metastable phases, phase transformations, and phase diagrams in physics and chemistry. Physics-Uspekhi, 2006, 49 (7), P. 719.Brazhkin V. V. Metastable phases, phase transformations, and phase diagrams in physics and chemistry. Physics-Uspekhi, 2006, 49 (7), P. 719.Brazhkin V. V. Interparticle interaction in condensed media: some elements are ’more equal than others’. Physics-Uspekhi, 2009, 52 (4), P. 369.Brazhkin V. V. Interparticle interaction in condensed media: some elements are ’more equal than others’. Physics-Uspekhi, 2009, 52 (4), P. 369.

The authors declare that there are no conflicts of interest present.