Carbon materials with high pentagon density
Source abstract
Abstract
Pentagons in carbon materials have attracted attentions because of the potential high chemical reactivity, band gap control, and electrochemical activity. However, it is challenging to prepare a carbon film with high pentagon density because of the curvature and the high reactivity caused by the presence of pentagons, and it is also challenging to estimate the percentage of pentagons in carbon materials because of the limitation of current analytical techniques. In this work, the percentage of pentagons in carbon materials was experimentally estimated for the first time using experimental and calculated C1s X-ray photoelectron spectroscopy and elemental analysis. Carbon films with 7% of pentagons (40% of pentagons compared to the raw material) with electrical resistivity of 1.1 × 104 Ω meter were prepared by heat treatment of corannulene at 873 K. On the other hand, fluoranthene and fullerene remained as non-film solid and powder without forming films at 873 K. Experimental and calculated Raman and IR spectra revealed the peaks of different types of pentagons. Decrement of pentagons in corannulene and fluoranthene heated at high temperatures can be explained mainly by the scission of C=C bond in pentagons, as suggested by the results of reactive molecular dynamics simulation (ReaxFF).
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Graphene research and applications · Carbon Nanotubes in Composites · Diamond and Carbon-based Materials Research
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (79)
Show source-provided references
1. Kroto HW, Heath JR, O'Brien SC, Curl RF, Smalley RE (1985) C60: Buckminsterfullerene. Nature 318:162–16310.1038/318162a0 ↗
2. Iijima S (1991) Helical microtubules of graphitic carbon. Nature 354:56–5810.1038/354056a0 ↗
3. Novoselov KS, Geim AK, Morozov SV, Jiang D, Zhang Y, Dubonos SV et al (2004) Electric field effect in atomically thin carbon films. Science 306:666–66910.1126/science.1102896 ↗
4. Novoselov KS, Geim AK, Morozov SV, Jiang D, Katsnel-son MI, Grigorieva IV et al (2005) Two-dimensional gas of massless Dirac fermions in graphene. Nature 438:197–20010.1038/nature04233 ↗
5. Zhu J, Huang Y, Mei W, Zhao C, Zhang C, Zhang J et al (2019) Effects of intrinsic pentagon defects on electrochemical reactivity of carbon nanomaterials. Angew Chem Int 58:1–710.1002/anie.201813481 ↗
6. Narita K, Okada S (2016) Geometric and electronic structures of corannulene polymers: ultra narrow graphene ribbons with corrugation and topological defects. Chem Phys Lett 650:76–8110.1016/j.cplett.2016.02.075 ↗
7. Wei Y, Wu J, Yin H, Shi X, Yang R, Dresselhaus M (2012) The nature of strength enhancement and weakening by pentagon-heptagon defects in graphene. Nat Mater 11:759–76310.1038/nmat3370 ↗
8. Cai J, Ruffieux P, Jaafar R, Bieri M, Braun T, Blankenburg S et al (2010) Atomically precise bottom-up fabrication of graphene nanoribbons. Nature 466:470–47310.1038/nature09211 ↗
9. Ruffieux P, Wang S, Yang B, Sánchez-Sánchez C, Liu J, Dienel T, Talirz L, Shinde P et al (2016) On-surface synthesis of graphene nanoribbons with zigzag edge topology. Nature 531:489–49310.1038/nature17151 ↗
10. Yamada Y, Gohda S, Abe K, Togo T, Shimano N, Sasaki T et al (2017) Carbon materials with controlled edge structures. Carbon 122:694–70110.1016/j.carbon.2017.07.012 ↗
11. Yamada Y, Kawai M, Yorimitsu H, Otsuka S, Takanashi M, Sato S (2018) Carbon materials with zigzag and armchair edges. ACS Appl Mater Interfaces 10:40710–4073910.1021/acsami.8b11022 ↗
12. Georgakilas V, Otyepka M, Bourlinos AB, Chandra V, Kim N, Kemp KC et al (2012) Functionalization of graphene: covalent and non-covalent approaches, derivatives and applications. Chem Rev 112:6156–621410.1021/cr3000412 ↗
13. Bottari G, Herranz MA, Wibmer L, Volland M, Rodrıguez-Perez L, Guldi DM et al (2017) Chemical functionalization and characterization of graphene-based materials. Chem Soc Rev 46:4464–450010.1039/C7CS00229G ↗
14. Kim J, Yamada Y, Suzuki Y, Ciston J, Sato S (2014) Pyrolysis of epoxidized fullerenes analyzed by spectroscopies. J Phys Chem C 118:7076–708410.1021/jp4120332 ↗
15. Jiang Y, Yang L, Sun T, Zhao J, Lyu Z, Zhuo O et al (2015) Significant contribution of intrinsic carbon defects to oxygen reduction activity. ACS Catal 5:6707–671210.1021/acscatal.5b01835 ↗
16. Han MY, Özyilmaz B, Zhang Y, Kim P (2007) Energy band-gap engineering of graphene nanoribbons. Phys Rev Lett 98:20680510.1103/PhysRevLett.98.206805 ↗
17. Cui L, Ren X, Wang J, Sun M (2020) Synthesis of homogeneous carbon quantum dots by ultrafast dual-beam pulsed laser ablation for bioimaging. Mater Today Nano 12:10009
18. Mu X, Sun M (2020) The linear and non-linear optical absorption and asymmetrical electromagnetic interaction in chiral twisted bilayer graphene with hybrid edges. Mater Today Phys 14:10022210.1016/j.mtphys.2020.100222 ↗
19. Banhart F, Kotakoski J, Krasheninnikov AV (2011) Structural defects in graphene. ACS Nano 5:26–4110.1021/nn102598m ↗
20. Huang PY, Ruiz-Vargas CS, van der Zande AM, Whitney WS, Levendorf MP, Kevek JW et al (2011) Grains and grain boundaries in single-layer graphene atomic patchwork quilts. Nature 469:389–39210.1038/nature09718 ↗
21. Scott LT, Boorum MM, McMahon BJ, Hagen S, Mack J, Blank J, Wegner H, De Meijere A (2002) A rational chemical synthesis of C60. Science 295:1500–150310.1126/science.1068427 ↗
22. Amsharov KY, Jansen MA (2008) C78 Fullerene precursor: toward the direct synthesis of higher fullerenes. J Org Chem 73:2931–293410.1021/jo7027008 ↗
23. Ono S, Toda Y, Onoe J (2014) Unified understanding of the electron-phonon coupling strength for nanocarbon allotropes. Phys Rev B 90:15543510.1103/PhysRevB.90.155435 ↗
24. Iwasa Y, Arima T, Fleming RM, Siegrist T, Zhou O, Haddon RC et al (1994) New phases of C60 synthesized at high pressure. Science 264:1570–157210.1126/science.264.5165.1570 ↗
25. Nuñez-Regueiro M, Marques L, Hodeau JL, Béthoux O, Perroux M (1995) Polymerized fullerite structures. Phys Rev Lett 74:278–28110.1103/PhysRevLett.74.278 ↗
26. Muzammil EM, Halilovic D, Stuparu MC (2019) Synthesis of corannulene-based nanographenes. Commun Chem 2:5810.1038/s42004-019-0160-1 ↗
27. Nestoros E, Stuparu MC (2018) Corannulene: a molecular bowl of carbon with multifaceted properties and diverse applications. Chem Commun 54:6503–651910.1039/C8CC02179A ↗
28. Zabula AV, Filatov AS, Spisak SN, Rogachev AY, Petrukhina MA (2011) A main group metal sandwich: five lithium cations jammed between two corannulene tetraanion decks. Science 333:1008–101110.1126/science.1208686 ↗
29. Yanney M, Fronczek FR, Henry WP, Beard DJ, Sygula A (2011) Cyclotrimerization of corannulyne: steric hindrance tunes the inversion barriers of corannulene bowls. Eur J Org Chem 2011:6636–663910.1002/ejoc.201101374 ↗
30. Kato K, Segawa Y, Scott LT, Itami K (2018) A quintuple [6]helicene with a corannulene core as a C5-symmetric propeller-shaped p-system. Angew Chem Int Ed 57:1337–134110.1002/anie.201711985 ↗
31. Inada Y (2015) Laser-induced carbonization of sumanene derivatives. Osaka University. Dissertation10.1039/C5RA00747J ↗
32. Fitzer E, Mueller K (1968) Paper No. 167. In: 8th Conference on carbon, Buffalo, 1967. Carbon, vol 6, p 23410.1016/0008-6223(68)90471-5 ↗
33. Ruland W (1965) X-ray studies on the carbonization and graphitization of acenaphthylene and bifluorenyl. Carbon 2:365–37810.1016/0008-6223(65)90007-2 ↗
34. Singer LS, Lewis IC (1965) An electron spin resonance study of the carbonization of the aromatic hydrocarbon acenaphthylene. Carbon 2:115–12010.1016/0008-6223(64)90050-8 ↗
35. Granda M, Santamaria R, Menendez R (2003) Chapter 4 Coal-tar pitch: composition and pyrolysis behavior. In: Radovic LR (ed) Chemistry and Physics of Carbon. Marcel Dekker, Inc, New York, pp 263–330
36. Mochida I, Miyasaka H, Fujitsu H, Takeshita K (1978) Carbonization properties of aromatic hydrocarbons containing five-membered ring. Tanso 92:7–16 (written in Japanese)10.7209/tanso.1978.7 ↗
37. Khlobystov AN (2011) Carbon nanotubes: from nano test tube to nano-reactor. ACS Nano 5:9306–931210.1021/nn204596p ↗
38. Zurek E, Pickard CJ, Autschbach J (2008) Density functional study of the 13C NMR chemical shifts in single-walled carbon nanotubes with Stone-Wales defects. J Phys Chem C 112:11744–1175010.1021/jp803180v ↗
39. Sun G, Kertesz M (2000) Theoretical 13C NMR spectra of IPR isomers of fullerenes C60, C70, C72, C74, C76, and C78 studied by density functional theory. J Phys Chem A 104:7398–740310.1021/jp001272r ↗
40. Hawelek L, Wrzalik W, Brodka A, Dore JC, Hannon AC, Iijima S et al (2011) A pulsed neutron diffraction study of the topological defects presence in carbon nanohorns. Chem Phys Lett 502:87–9110.1016/j.cplett.2010.12.026 ↗
41. Kim J, Yamada Y, Kawai M, Tanabe T, Sato S (2015) Spectral change of simulated X-ray photoelectron spectroscopy from graphene to fullerene. J Mater Sci 50:6739–6747. https://doi.org/10.1007/s10853-015-9229-010.1007/s10853-015-9229-0 ↗
42. Yamada Y, Yasuda H, Murota K, Nakamura M, Sodesawa T, Sato S (2013) Analysis of heat-treated graphite oxide by X-ray photoelectron spectroscopy. J Mater Sci 48:8171–8198. https://doi.org/10.1007/s10853-013-7630-010.1007/s10853-013-7630-0 ↗
43. Yamada Y, Sato S (2015) Structural analysis of carbon materials by X-ray photoelectron spectroscopy using computational chemistry. Tanso 269:181–189 (written in Japanese)10.7209/tanso.2015.181 ↗
44. Yamada Y, Kim J, Matsuo S, Sato S (2014) Nitrogen-containing graphene analyzed by X-ray photoelectron spectroscopy. Carbon 70:59–7410.1016/j.carbon.2013.12.061 ↗
45. Yamada Y, Matsuo S, Abe K, Kubo S, Sato S (2016) Selective doping of nitrogen into carbon materials without catalysts. J Mater Sci 51:8900–8915. https://doi.org/10.1007/s10853-016-0142-y10.1007/s10853-016-0142-y ↗
46. Fujimoto A, Yamada Y, Koinuma M, Sato S (2016) Origins of sp3C peaks in C1s X-ray photoelectron spectra of carbon materials. Anal Chem 88:6110–611410.1021/acs.analchem.6b01327 ↗
47. Kim J, Lee N, Nodo M, Min YH, Noh SH, Kim N et al (2018) Distinguishing zigzag and armchair edges on graphene nanoribbons by X-ray photoelectron and Raman spectroscopies. ACS Omega 3:17789–1779610.1021/acsomega.8b02744 ↗
48. Nishihara H, Hirota T, Matsuura K, Ohwada M, Hoshino N, Akutagawa T et al (2017) Synthesis of ordered carbonaceous frameworks from organic crystals. Nat Commun 8:10910.1038/s41467-017-00152-z ↗
49. Saha B, Schatz GC (2012) Carbonization in polyacrylonitrile (PAN) based carbon fibers studied by ReaxFF molecular dynamics simulations. J Phys Chem B 116:4684–469210.1021/jp300581b ↗
50. Li K, Zhang H, Li G, Zhang J, Bouhadja M, Liu Z et al (2018) ReaxFF molecular dynamics simulation for the graphitization of amorphous carbon: a parametric study. J Chem Theory Comput 14:2322–233110.1021/acs.jctc.7b01296 ↗
51. Senda T, Yamada Y, Morimoto M, Nono N, Sogabe T, Kubo S et al (2019) Analyses of oxidation process for isotropic pitch-based carbon fiber using model compounds. Carbon 142:311–32610.1016/j.carbon.2018.10.026 ↗
52. Sasaki T, Yamada Y, Sato S (2018) Quantitative analysis of zigzag and armchair edges on carbon materials with and without pentagons using infrared spectroscopy. Anal Chem 90:10724–1073110.1021/acs.analchem.8b00949 ↗
53. Yamada Y, Murota K, Fujita R, Kim J, Watanabe A, Nakamura M et al (2014) Subnanometer vacancy defects introduced on graphene by oxygen gas. J Am Chem Soc 136:2232–223510.1021/ja4117268 ↗
54. Eckmann A, Felten A, Mishchenko A, Britnell L, Krupke R, Novoselov KS et al (2012) Probing the nature of defects in graphene by Raman spectroscopy. Nano Lett 12:3925–393010.1021/nl300901a ↗
55. Malard LM, Pimenta MA, Dresselhaus G, Dresselhaus MS (2009) Raman spectroscopy in graphene. Phys Rep 473:51–8710.1016/j.physrep.2009.02.003 ↗
56. Nemanich RJ, Solin SA (1979) First- and second-order Raman scattering from finite-size crystals of graphite. Phys Rev B 20:392–40110.1103/PhysRevB.20.392 ↗
57. IUPAC (1997) Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by McNaught AD and Wilkinson A Blackwell Scientific Publications, Oxford (1997). Online version (2019-) created by Chalk SJ. ISBN 0-9678550-9-8. https://doi.org/10.1351/goldbook.C0084010.1351/goldbook.C00840 ↗
58. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR et al (2009) Gaussian 09, revision E.01. Gaussian Inc, Wallingford, CT
59. Computational Chemistry Comparison and Benchmark Data Base, NIST, https://cccbdb.nist.gov/vibscalejust.asp, as of July 2, 2020
60. Liu L, Liu Y, Zybin SV, Sun H, Goddard WA III (2011) ReaxFF-lg: correction of the ReaxFF reactive force field for London dispersion, with applications to the equations of state for energetic Materials. J Phys Chem A 115:11016–1102210.1021/jp201599t ↗
61. Menon A, Dreyer JAH, Martin JW, Akroyd J, Robertson J, Kraft M (2019) Optical band gap of cross-linked, curved, and radical polyaromatic hydrocarbons. Phys Chem Chem Phys 21:16240–1625110.1039/C9CP02363A ↗
62. Terrones M, Terrones H, Banhart F, Charlier J, Ajayan P (2000) Coalescence of single-walled carbon nanotubes. Science 288:1226–122910.1126/science.288.5469.1226 ↗
63. Martin JW, McIntosh GJ, Arul R, Oosterbeek RN, Kraft M, Söhnel T (2017) Giant fullerene formation through thermal treatment of fullerene soot. Carbon 125:132–13810.1016/j.carbon.2017.09.045 ↗
64. Gutman I, Ruiz-Morales Y (2007) Note on the Y-rule in Clar theory. Polycycl Aromat Comp 27:41–4910.1080/10406630601134268 ↗
65. Solà M (2013) Forty years of Clar's aromatic π-sextet rule. Front Chem 1:2210.3389/fchem.2013.00022 ↗
66. Chung DDL (2003) Review graphite. J Mater Sci 37:1475–1489. https://doi.org/10.1023/A:101491530773810.1023/A:1014915307738 ↗
67. Martin JW, Hou D, Menon A, Pascazio L, Akroyd J, You X, Kraft M (2019) Reactivity of polycyclic aromatic hydrocarbon soot precursors:implications of localized π-radicals on rim-based pentagonal rings. J Phys Chem C 123:26673–2668210.1021/acs.jpcc.9b07558 ↗
68. Whitesides R, Frenklach M (2010) Detailed kinetic Monte Carlo simulations of graphene-edge growth. J Phys Chem A 114:689–70310.1021/jp906541a ↗
69. Singh RI, Mebel AM, Frenklach M (2015) Oxidation of graphene-edge six- and five-member rings by molecular oxygen. J Phys Chem A 119:7528–754710.1021/acs.jpca.5b00868 ↗
70. Violi A (2005) Cyclodehydrogenation reactions to cyclopentafused polycyclic aromatic hydrocarbons. J Phys Chem A 109:7781–778710.1021/jp052384r ↗
71. Chanyshev AD, Litasov KD, Shatskiy AF, Furukawa Y, Yoshino T, Ohtani E (2015) Oligomerization and carbonization of polycyclic aromatic hydrocarbons at high pressure and temperature. Carbon 84:225–23510.1016/j.carbon.2014.12.011 ↗
72. Ōsawa S, Ōsawa E, Hirose Y (1995) Doubly bonded C60 dimers and congeners: computational studies of structures, bond energies and transformations. Fullerene Sci Technol 3:565–58510.1080/153638X9508543808 ↗
73. Sabirov DS (2013) Polarizability of C60 fullerene dimer and oligomers: the unexpected enhancement and its use for rational design of fullerene-based nanostructures with adjustable properties. RSC Adv 3:19430–1943910.1039/c3ra42498g ↗
74. Koshino M, Niimi Y, Nakamura E, Kataura H, Okazaki T, Suenaga K, Iijima S (2010) Analysis of the reactivity and selectivity of fullerene dimerization reactions at the atomic level. Nat Chem 2:117–12410.1038/nchem.482 ↗
75. Schettino V, Pagliai M, Ciabini L, Cardini G (2001) The vibrational spectrum of fullerene C60. J Phys Chem A 105:11192–1119610.1021/jp012874t ↗
76. Yamada Y (2008) Chung DDL (2008) Three-dimensional microstructuring of carbon by thermoplastic spacer evaporation during pyrolysis. Carbon 46:1765–177210.1016/j.carbon.2008.07.031 ↗
77. Yamada Y, Chung DDL (2008) Epoxy-based carbon films with high electrical conductivity attached to an alumina substrate. Carbon 46:1798–180110.1016/j.carbon.2008.07.001 ↗
78. Tanabe T, Yamada Y, Kim J, Koinuma M, Kubo S, Shimano N, Sato S (2016) Knoevenagel condensation using nitrogen-doped carbon catalysts. Carbon 109:208–22010.1016/j.carbon.2016.08.003 ↗
79. Khan SM, Kitayama H, Yamada Y, Gohda S, Ono H, Umeda D, Abe K, Hata K, Ohba T (2018) High CO2 sensitivity and reversibility on nitrogen-containing polymer by remarkable CO2 adsorption on nitrogen sites. J Phys Chem C 122:24143–2414910.1021/acs.jpcc.8b07420 ↗