PH-driven, reversible epoxy ring opening/closing in graphene oxide

Carbon

Volumn 84, Issue 1, 2015, Pages 560-566

  Taniguchi, Takaaki ^a,b   Kurihara, Seiji ^a,b   Tateishi, Hikaru ^a,b   Hatakeyama, Kazuto ^a,b   Koinuma, Michio ^a,b   Yokoi, Hiroyuki ^a,b   Hara, Masahiro ^a,b   Ishikawa, Hayato ^a   Matsumoto, Yasumichi ^a,b  

^a KUMAMOTO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL GROUPS; GRAPHENE;

ACID TREATMENTS; ALKALINE CONDITIONS; ALKALINE SOLUTIONS; AMBIENT CONDITIONS; EPOXIDE OPENINGS; EPOXIDE RING OPENING; FLUX CONDITIONS; OXYGEN FUNCTIONAL GROUPS;

ALKALINITY;

EID: 84922218902     PISSN: 00086223     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbon.2014.12.054     Document Type: Article

References (37)

1. Hernandez Y, Nicolosi V, Lotya M, Blighe FM, Sun Z, De S, et al. High-yield production of graphene by liquid-phase exfoliation of graphite. Nat Nanotechnol 2008;3:563-8.
2. Dreyer DR, Park S, Bielawski CW, Ruoff RS. The chemistry of graphene oxide. Chem Soc Rev 2010;39:228-40.
3. Georgakilas V, Otyepka M, Bourlinos AB, Chandra V, Kim N, Kemp KC, et al. Functionalization of graphene: covalent and non-covalent approaches, derivatives and applications. Chem Rev 2012;112:6156-214.
4. Yang K, Feng L, Shi X, Liu Z. Nano-graphene in biomedicine: theranostic applications. Chem Soc Rev 2013;42:530-47.
5. Jung J, Lim H, Oh J, Kim Y. Functionalization of graphene grown on metal substrate with atomic oxygen: enolate vs epoxide. J Am Chem Soc 2014;136:8528-31.
6. Kumar PV, Bardhan NM, Tongay S, Wu J, Belcher AM, Grossman JC. Scalable enhancement of graphene oxide properties by thermally driven phase transformation. Nat Chem 2014;6:151-8.
7. Su C, Acik M, Takai K, Lu J, Hao SJ, Zheng Y, et al. Probing the catalytic activity of porous graphene oxide and the origin of this behaviour. Nat Commun 2012;3.
8. Fan X, Peng W, Li Y, Li X, Wang S, Zhang G, et al. Deoxygenation of exfoliated graphite oxide under alkaline conditions: a green route to graphene preparation. Adv Mater 2008;20:4490-3.
9. Rourke JP, Pandey PA, Moore JJ, Bates M, Kinloch IA, Young RJ, et al. The real graphene oxide revealed: stripping the oxidative debris from the graphene-like sheets. Angew Chem Int Ed 2011;50:3173-7.
10. Lõpez-Díaz D, Velázquez MM, De La Torre SB, Pérez-Pisonero A, Trujillano R, Fierro JLG, et al. The role of oxidative debris on graphene oxide films. ChemPhysChem 2013;14:4002-9.
11. Faria AF, Martinez DST, Moraes ACM, Maia Da Costa MEH, Barros EB, Souza FilhoAG, et al.Unveiling the role of oxidation debris on the surface chemistry of graphene through the anchoring of Ag nanoparticles. Chem Mater 2012;24:4080-7.
12. Dimiev AM, Alemany LB, Tour JM. Graphene oxide. Origin of acidity, its instability in water, and a new dynamic structural model. ACS Nano 2013;7:576-88.
13. Hatakeyama K, Razaul Karim M, Ogata C, Tateishi H, Taniguchi T, Koinuma M, et al. Optimization of proton conductivity in graphene oxide by filling sulfate ions. Chem Commun 2014;50:14527-30.
14. Hatakeyama K, Karim MR, Ogata C, Tateishi H, Funatsu A, Taniguchi T, et al. Proton conductivities of graphene oxide nanosheets: single, multilayer, and modified nanosheets. Angew Chem Int Ed 2014;53:6997-7000.
15. Ogata C, Koinuma M, Hatakeyama K, Tateishi H, Asrori MZ, Taniguchi T, et al. Metal permeation into multi-layered graphene oxide. Sci Rep 2014;4:3647.
16. Tateishi H, Koinuma M, Miyamoto S, Kamei Y, Hatakeyama K, Ogata C, et al. Effect of the electrochemical oxidation/reduction cycle on the electrochemical capacitance of graphite oxide. Carbon 2014;76:40-5.
17. Stankovich S, Dikin DA, Piner RD, Kohlhaas KA, Kleinhammes A, Jia Y, et al. Synthesis of graphene-based nanosheets via chemical reduction of exfoliated graphite oxide. Carbon 2007;45:1558-65.
18. Matsumoto Y, Koinuma M, Kim SY, Watanabe Y, Taniguchi T, Hatakeyama K, et al. Simple photoreduction of graphene oxide nanosheet under mild conditions. ACS Appl Mater Interfaces 2010;2:3461-6.
19. Zhu Y, Stoller MD, Cai W, Velamakanni A, Piner RD, Chen D, et al. Exfoliation of graphite oxide in propylene carbonate and thermal reduction of the resulting graphene oxide platelets. ACS Nano 2010;4:1227-33.
20. Kim F, Luo J, Cruz-Silva R, Cote LJ, Sohn K, Huang J. Selfpropagating domino-like reactions in oxidized graphite. Adv Funct Mater 2010;20:2867-73.
21. Canado LG, Takai K, Enoki T, Endo M, Kim YA, Mizusaki H, et al. General equation for the determination of the crystallite size la of nanographite by Raman spectroscopy. Appl Phys Lett 2006;88:0252.
22. Ryu S, Han MY, Maultzsch J, Heinz TF, Kim P, Steigerwald ML, et al. Reversible basal plane hydrogenation of graphene. Nano Lett 2008;8:4597-602.
23. Kim MC, Hwang GS, Ruoff RS. Epoxide reduction with hydrazine on graphene: a first principles study. J Chem Phys 2009;131:25.
24. Thomas HR, Marsden AJ, Walker M, Wilson NR, Rourke JP. Sulfur-functionalized graphene oxide by epoxide ringopening. Angew Chem Int Ed 2014;53:7613-8.
25. Cai W, Piner RD, Stadermann FJ, Park S, Shaibat MA, Ishii Y, et al. Synthesis and solid-state NMR structural characterization of 13C-labeled graphite oxide. Science 2008;321:1815-7.
26. Acik M, Mattevi C, Gong C, Lee G, Cho K, Chhowalla M, et al. The role of intercalated water in multilayered graphene oxide. ACS Nano 2010;4:5861-8.
27. Bruice PY. Organic chemistry. 5th ed. Pearson Education, Inc.; 2007 [Chapter 10].
28. Pocker Y, Ronald BP. Kinetics and mechanism of vic-diol dehydration. II. p-Anisyl group in pinacolic rearrangement. J Org Chem 1970;35:3362-7.
29. Itoh S, Yamataka H. Reaction pathway of aliphatic pinacoltype rearrangement reexamined. J Phys Org Chem 2010;23:789-95.
30. Karim MR, Hatakeyama K, Matsui T, Takehira H, Taniguchi T, Koinuma M, et al. Graphene oxide nanosheet with high proton conductivity. J Am Chem Soc 2013;135:8097-100.
31. Gao W, Wu G, Janicke MT, Cullen DA, Mukundan R, Baldwin JK, et al. Ozonated graphene oxide film as a proton-exchange membrane. Angew Chem Int Ed 2014;53:3588-93.
32. Gao X, Jang J, Nagase S. Hydrazine and thermal reduction of graphene oxide: reaction mechanisms, product structures, and reaction design. J Phys Chem C 2009;114:832-42.
33. Zhang XF, Shao X, Liu S. Dual fluorescence of graphene oxide: a time-resolved study. J Phys Chem A 2012;116:7308-13.
34. Shang J, Ma L, Li J, Ai W, Yu T, Gurzadyan GG. The origin of fluorescence from graphene oxide. Sci Rep 2012;2.
35. Pan D, Zhang J, Li Z, Wu C, Yan X, Wu M. Observation of pH-, solvent-, spin-, and excitation-dependent blue photoluminescence from carbon nanoparticles. Chem Commun 2010;46:3681-3.
36. Eda G, Lin YY, Mattevi C, Yamaguchi H, Chen HA, Chen IS, et al. Blue photoluminescence from chemically derived graphene oxide. Adv Mater 2010;22:505-9.
37. Zhu X, Su H. Exciton characteristics in graphene epoxide. ACS Nano 2014;8:1284-9.