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The Chemistry of Graphene Oxide

  • Chapter
Graphene Oxide

Abstract

In this chapter, we discuss a variety of chemical reactions introduced for GO. Among all studies on the chemistry of GO, the largest portion focused on the reduction of GO back to graphene, mainly due to its high relevance to graphene and the gold rush of graphene research over the last decade. However, doping, functionalization and cross-linking of GO are equally, if not more, interesting to chemists, since GO is a giant model compound of polycyclic aromatic hydrocarbon (PAH) oxides. Here, we start with a thorough comparison between various reducing recipes for GO, and follow with some theoretical simulations and predictions on its convertibility toward graphene. In addition to that, we elaborate on extended chemical modifications (covalent and non-covalent), cross-linking, and doping recipes for this macromolecule shown in literature. After all, we intend to show you that GO became a relatively hot research topic, not only due to its relevance to graphene, but also for its high chemical activity and tunability, which enabled the prosperity of its research in various fields led by chemists, materials scientists, biologists, physicists, as well as engineers. It is a perfect paradigm for young researchers as an important subject thrived in interdisciplinary research. After all, when real-life problems come, potential solutions do not impose boundaries between disciplines. All relevant disciplines can offer their input, and contribute together to the final solutions, in which cases communications and collaborations between different researchers need to be encouraged and appreciated.

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References

  1. Becerril HA, Mao J, Liu Z, Stoltenberg RM, Bao Z, Chen Y (2008) Evaluation of solution-processed reduced graphene oxide films as transparent conductors. ACS Nano 2:463–470

    Google Scholar 

  2. Gomez-Navarro C, Weitz RT, Bittner AM, Scolari M, Mews A, Burghard M, Kern K (2007) Electronic transport properties of individual chemically reduced graphene oxide sheets. Nano Lett 7:3499–3503

    Google Scholar 

  3. Stankovich S, Piner RD, Chen XQ, Wu NQ, Nguyen ST, Ruoff RS (2006) Stable aqueous dispersions of graphitic nanoplatelets via the reduction of exfoliated graphite oxide in the presence of poly(sodium 4-styrenesulfonate). J Mater Chem 16:155–158

    Google Scholar 

  4. Si Y, Samulski ET (2008) Synthesis of water soluble graphene. Nano Lett 8:1679–1682

    Google Scholar 

  5. Kim J, Cote LJ, Kim F, Yuan W, Shull KR, Huang J (2010) Graphene oxide sheets at interfaces. J Am Chem Soc 132:8180–8186

    Google Scholar 

  6. Paredes JI, Villar-Rodil S, Martinez-Alonso A, Tascon JMD (2008) Graphene oxide dispersions in organic solvents. Langmuir 24:10560–10564

    Google Scholar 

  7. Cote LJ, Kim J, Tung VC, Luo JY, Kim F, Huang JX (2011) Graphene oxide as surfactant sheets. Pure Appl Chem 83:95–110

    Google Scholar 

  8. Cote LJ, Kim F, Huang J (2008) Langmuir-Blodgett assembly of graphite oxide single layers. J Am Chem Soc 131:1043–1049

    Google Scholar 

  9. Cote LJ, Kim J, Zhang Z, Sun C, Huang J (2010) Tunable assembly of graphene oxide surfactant sheets: wrinkles, overlaps and impacts on thin film properties. Soft Matter 6

    Google Scholar 

  10. Kim F, Cote LJ, Huang J (2009) Graphene oxide: surface activity and two-dimensional assembly. Adv Mater 22:1954–1958

    Google Scholar 

  11. Hofmann U, Frenzel A (1934) The reduction of graphite oxide with hydrogen sulphide. Koll Zeitschr 68:149–151

    Google Scholar 

  12. Kim J, Im H, Kim J-M, Kim J (2012) Thermal and electrical conductivity of Al(OH)3 covered graphene oxide nanosheet/epoxy composites. J Mater Sci 47:1418–1426

    Google Scholar 

  13. Stankovich S, Dikin DA, Piner RD, Kohlhaas KA, Kleinhammes A, Jia Y, Wu Y, Nguyen ST, Ruoff RS (2007) Synthesis of graphene-based nanosheets via chemical reduction of exfoliated graphite oxide. Carbon 45:1558–1565

    Google Scholar 

  14. Kuila T, Mishra AK, Khanra P, Kim NH, Lee JH (2013) Recent advances in the efficient reduction of graphene oxide and its application as energy storage electrode materials. Nanoscale 5:52–71

    Google Scholar 

  15. Luo D, Zhang G, Liu J, Sun X (2011) Evaluation criteria for reduced graphene oxide. J Phys Chem C 115:11327–11335

    Google Scholar 

  16. Pei S, Cheng H-M (2012) The reduction of graphene oxide. Carbon 50:3210–3228

    Google Scholar 

  17. Gao W, Alemany LB, Ci L, Ajayan PM (2009) New insights into the structure and reduction of graphite oxide. Nat Chem 1:403–408

    Google Scholar 

  18. Park S, An JH, Piner RD, Jung I, Yang DX, Velamakanni A, Nguyen ST, Ruoff RS (2008) Aqueous suspension and characterization of chemically modified graphene sheets. Chem Mater 20:6592–6594

    Google Scholar 

  19. Shin HJ, Kim KK, Benayad A, Yoon SM, Park HK, Jung IS, Jin MH, Jeong HK, Kim JM, Choi JY, Lee YH (2009) Efficient reduction of graphite oxide by sodium borohydride and its effect on electrical conductance. Adv Funct Mater 19:1987–1992

    Google Scholar 

  20. Park S, An J, Potts JR, Velamakanni A, Murali S, Ruoff RS (2011) Hydrazine-reduction of graphite-and graphene oxide. Carbon 49:3019–3023

    Google Scholar 

  21. Obata S, Tanaka H, Saiki K (2013) Electrical and spectroscopic investigations on the reduction mechanism of graphene oxide. Carbon 55:126–132

    Google Scholar 

  22. Niu Z, Chen J, Hng HH, Ma J, Chen X (2012) A leavening strategy to prepare reduced graphene oxide foams. Adv Mater 24:4144–4150

    Google Scholar 

  23. Tung VC, Allen MJ, Yang Y, Kaner RB (2009) High-throughput solution processing of large-scale graphene. Nat Nanotechnol 4:25–29

    Google Scholar 

  24. Gilje S, Han S, Wang M, Wang KL, Kaner RB (2007) A chemical route to graphene for device applications. Nano Lett 7:3394–3398

    Google Scholar 

  25. Stankovich S, Dikin DA, Dommett GHB, Kohlhaas KM, Zimney EJ, Stach EA, Piner RD, Nguyen ST, Ruoff RS (2006) Graphene-based composite materials. Nature 442:282–286

    Google Scholar 

  26. Yun JM, Yeo JS, Kim J, Jeong HG, Kim DY, Noh YJ, Kim SS, Ku BC, Na SI (2011) Solution-processable reduced graphene oxide as a novel alternative to PEDOT:PSS hole transport layers for highly efficient and stable polymer solar cells. Adv Mater 23:4923–4928

    Google Scholar 

  27. Liu J, Jeong H, Liu J, Lee K, Park JY, Ahn YH, Lee S (2010) Reduction of functionalized graphite oxides by trioctylphosphine in non-polar organic solvents. Carbon 48:2282–2289

    Google Scholar 

  28. Moon IK, Lee J, Ruoff RS, Lee H (2010) Reduced graphene oxide by chemical graphitization. Nat Commun 1:73

    Google Scholar 

  29. Cataldo F, Ursini O, Angelini G (2011) Graphite oxide and graphene nanoribbons reduction with hydrogen iodide. Fuller Nanotub Car N 19:461–468

    Google Scholar 

  30. Das AK, Srivastav M, Layek RK, Uddin ME, Jung D, Kim NH, Lee JH (2014) Iodide-mediated room temperature reduction of graphene oxide: a rapid chemical route for the synthesis of a bifunctional electrocatalyst. J Mater Chem A 2:1332–1340

    Google Scholar 

  31. Esfandiar A, Akhavan O, Irajizad A (2011) Melatonin as a powerful bio-antioxidant for reduction of graphene oxide. J Mater Chem 21:10907–10914

    Google Scholar 

  32. Liao KH, Mittal A, Bose S, Leighton C, Mkhoyan KA, Macosko CW (2011) Aqueous only route toward graphene from graphite oxide. ACS Nano 5:1253–1258

    Google Scholar 

  33. Han TH, Huang Y-K, Tan ATL, Dravid VP, Huang J (2011) Steam etched porous graphene oxide network for chemical sensing. J Am Chem Soc 133:15264–15267

    Google Scholar 

  34. Thakur S, Karak N (2012) Green reduction of graphene oxide by aqueous phytoextracts. Carbon 50:5331–5339

    Google Scholar 

  35. Long Y, Zhang CC, Wang XX, Gao JP, Wang W, Liu Y (2011) Oxidation of SO(2) to SO(3) catalyzed by graphene oxide foams. J Mater Chem 21:13934–13941

    Google Scholar 

  36. Moon IK, Lee J, Lee H (2011) Highly qualified reduced graphene oxides: the best chemical reduction. Chem Commun 47:9681–9683

    Google Scholar 

  37. Jung H, Yang SJ, Kim T, Kang JH, Park CR (2013) Ultrafast room-temperature reduction of graphene oxide to graphene with excellent dispersibility by lithium naphthalenide. Carbon 63:165–174

    Google Scholar 

  38. Zhang S, Shao Y, Liao H, Engelhard MH, Yin G, Lin Y (2011) Polyelectrolyte-induced reduction of exfoliated graphite oxide: a facile route to synthesis of soluble graphene nanosheets. ACS Nano 5:1785–1791

    Google Scholar 

  39. Pei S, Zhao J, Du J, Ren W, Cheng H-M (2010) Direct reduction of graphene oxide films into highly conductive and flexible graphene films by hydrohalic acids. Carbon 48:4466–4474

    Google Scholar 

  40. Byon HR, Suntivich J, Shao-Horn Y (2011) Graphene-based non-noble-metal catalysts for oxygen reduction reaction in acid. Chem Mater 23:3421–3428

    Google Scholar 

  41. Zhou X, Zhang J, Wu H, Yang H, Zhang J, Guo S (2011) Reducing graphene oxide via hydroxylamine: a simple and efficient route to graphene. J Phys Chem C 115:11957–11961

    Google Scholar 

  42. Liu S, Tian J, Wang L, Sun X (2011) A method for the production of reduced graphene oxide using benzylamine as a reducing and stabilizing agent and its subsequent decoration with Ag nanoparticles for enzymeless hydrogen peroxide detection. Carbon 49:3158–3164

    Google Scholar 

  43. Xu LQ, Yang WJ, Neoh K-G, Kang E-T, Fu GD (2010) Dopamine-induced reduction and functionalization of graphene oxide nanosheets. Macromolecules 43:8336–8339

    Google Scholar 

  44. Tran DN, Kabiri S, Losic D (2014) A green approach for the reduction of graphene oxide nanosheets using non-aromatic amino acids. Carbon 76:193–202

    Google Scholar 

  45. Chua CK, Pumera M (2013) Selective removal of hydroxyl groups from graphene oxide. Chem Eur J 19:2005–2011

    Google Scholar 

  46. Wang K, Feng T, Qian M, Ding HI, Chen YW, Sun ZO (2011) The field emission of vacuum filtered graphene films reduced by microwave. Appl Surf Sci 257:5808–5812

    Google Scholar 

  47. Murugan AV, Muraliganth T, Manthiram A (2009) Rapid, facile microwave-solvothermal synthesis of graphene nanosheets and their polyaniline nanocomposites for energy storage. Chem Mater 21:5004–5006

    Google Scholar 

  48. Chen WF, Yan LF, Bangal PR (2010) Preparation of graphene by the rapid and mild thermal reduction of graphene oxide induced by microwaves. Carbon 48:1146–1152

    Google Scholar 

  49. Wang D-W, Wu K-H, Gentle IR, Lu GQ (2012) Anodic chlorine/nitrogen co-doping of reduced graphene oxide films at room temperature. Carbon 50:3333–3341

    Google Scholar 

  50. Zhou TN, Chen F, Liu K, Deng H, Zhang Q, Feng JW, Fu QA (2011) A simple and efficient method to prepare graphene by reduction of graphite oxide with sodium hydrosulfite. Nanotechnology 22:045704

    Google Scholar 

  51. Liao RJ, Tang ZH, Lei YD, Guo BC (2011) Polyphenol-reduced graphene oxide: mechanism and derivatization. J Phys Chem C 115:20740–20746

    Google Scholar 

  52. Seo M, Yoon D, Hwang KS, Kang JW, Kim J (2013) Supercritical alcohols as solvents and reducing agents for the synthesis of reduced graphene oxide. Carbon 64:207–218

    Google Scholar 

  53. Chen C, Chen T, Wang H, Sun G, Yang X (2011) A rapid, one-step, variable-valence metal ion assisted reduction method for graphene oxide. Nanotechnology 22(40):405602

    Google Scholar 

  54. Jung I, Dikin DA, Piner RD, Ruoff RS (2008) Tunable electrical conductivity of individual graphene oxide sheets reduced at “low” temperatures. Nano Lett 8:4283–4287

    Google Scholar 

  55. Wang S, Ang PK, Wang Z, Tang ALL, Thong JTL, Loh KP (2009) High mobility, printable, and solution-processed graphene electronics. Nano Lett 10:92–98

    Google Scholar 

  56. Chen WF, Yan LF (2010) Preparation of graphene by a low-temperature thermal reduction at atmosphere pressure. Nanoscale 2:559–563

    Google Scholar 

  57. Zhu YW, Stoller MD, Cai WW, Velamakanni A, Piner RD, Chen D, Ruoff RS (2010) Exfoliation of graphite oxide in propylene carbonate and thermal reduction of the resulting graphene oxide platelets. ACS Nano 4:1227–1233

    Google Scholar 

  58. Nethravathi C, Rajamathi M (2008) Chemically modified graphene sheets produced by the solvothermal reduction of colloidal dispersions of graphite oxide. Carbon 46:1994–1998

    Google Scholar 

  59. Zhou M, Wang YL, Zhai YM, Zhai JF, Ren W, Wang FA, Dong SJ (2009) Controlled synthesis of large-area and patterned electrochemically reduced graphene oxide films. Chem Eur J 15:6116–6120

    Google Scholar 

  60. Chen WF, Yan LF, Bangal PR (2010) Chemical reduction of graphene oxide to graphene by sulfur-containing compounds. J Phys Chem C 114:19885–19890

    Google Scholar 

  61. Gao X, Tang XS (2014) Effective reduction of graphene oxide thin films by a fluorinating agent: diethylaminosulfur trifluoride. Carbon 76:133–140

    MathSciNet  Google Scholar 

  62. Ahmed MS, Han HS, Jeon S (2013) One-step chemical reduction of graphene oxide with oligothiophene for improved electrocatalytic oxygen reduction reactions. Carbon 61:164–172

    Google Scholar 

  63. Ma Q, Song J, Jin C, Li Z, Liu J, Meng S, Zhao J, Guo Y (2013) A rapid and easy approach for the reduction of graphene oxide by formamidinesulfinic acid. Carbon 54:36–41

    Google Scholar 

  64. Fernandez-Merino MJ, Guardia L, Paredes JI, Villar-Rodil S, Solis-Fernandez P, Martinez-Alonso A, Tascon JMD (2010) Vitamin C is an ideal substitute for hydrazine in the reduction of graphene oxide suspensions. J Phys Chem C 114:6426–6432

    Google Scholar 

  65. Sui Z, Zhang X, Lei Y, Luo Y (2011) Easy and green synthesis of reduced graphite oxide-based hydrogels. Carbon 49:4314–4321

    Google Scholar 

  66. Gao J, Liu F, Liu YL, Ma N, Wang ZQ, Zhang X (2010) Environment-friendly method to produce graphene that employs vitamin C and amino acid. Chem Mater 22:2213–2218

    Google Scholar 

  67. Dua V, Surwade SP, Ammu S, Agnihotra SR, Jain S, Roberts KE, Park S, Ruoff RS, Manohar SK (2010) All-organic vapor sensor using inkjet-printed reduced graphene oxide. Angew Chem Int Ed 49:2154–2157

    Google Scholar 

  68. Chen Y, Shen Y, Sun D, Zhang H, Tian D, Zhang J, Zhu J-J (2011) Fabrication of a dispersible graphene/gold nanoclusters hybrid and its potential application in electrogenerated chemiluminescence. Chem Commun (Camb) 47:11733–5

    Google Scholar 

  69. Kuila T, Bose S, Khanra P, Mishra AK, Kim NH, Lee JH (2012) A green approach for the reduction of graphene oxide by wild carrot root. Carbon 50:914–921

    Google Scholar 

  70. Chu H-J, Lee C-Y, Tai N-H (2014) Green reduction of graphene oxide by Hibiscus sabdariffa L. to fabricate flexible graphene electrode. Carbon 80:725–733

    Google Scholar 

  71. Fan XB, Peng WC, Li Y, Li XY, Wang SL, Zhang GL, Zhang FB (2008) Deoxygenation of exfoliated graphite oxide under alkaline conditions: a green route to graphene preparation. Adv Mater 20:4490–4493

    Google Scholar 

  72. Zhu CZ, Guo SJ, Fang YX, Dong SJ (2010) Reducing sugar: new functional molecules for the green synthesis of graphene nanosheets. ACS Nano 4:2429–2437

    Google Scholar 

  73. Liu JB, Fu SH, Yuan B, Li YL, Deng ZX (2010) Toward a universal “adhesive nanosheet” for the assembly of multiple nanoparticles based on a protein-induced reduction/decoration of graphene oxide. J Am Chem Soc 132:7279–7281

    Google Scholar 

  74. Chen JL, Yan XP (2010) A dehydration and stabilizer-free approach to production of stable water dispersions of graphene nanosheets. J Mater Chem 20:4328–4332

    Google Scholar 

  75. Guo HL, Wang XF, Qian QY, Wang FB, Xia XH (2009) A green approach to the synthesis of graphene nanosheets. ACS Nano 3:2653–2659

    Google Scholar 

  76. Sundaram RS, Gomez-Navarro C, Balasubramanian K, Burghard M, Kern K (2008) Electrochemical modification of graphene. Adv Mater 20:3050–3053

    Google Scholar 

  77. Ping J, Wang Y, Fan K, Wu J, Ying Y (2011) Direct electrochemical reduction of graphene oxide on ionic liquid doped screen-printed electrode and its electrochemical biosensing application. Biosens Bioelectron 28:204–209

    Google Scholar 

  78. Guo Y, Wu B, Liu H, Ma Y, Yang Y, Zheng J, Yu G, Liu Y (2011) Electrical assembly and reduction of graphene oxide in a single solution step for use in flexible sensors. Adv Mater 23:4626–30

    Google Scholar 

  79. Ramesha GK, Sampath S (2009) Electrochemical reduction of oriented graphene oxide films: an in situ Raman spectroelectrochemical study. J Phys Chem C 113:7985–7989

    Google Scholar 

  80. Shao YY, Wang J, Engelhard M, Wang CM, Lin YH (2010) Facile and controllable electrochemical reduction of graphene oxide and its applications. J Mater Chem 20:743–748

    Google Scholar 

  81. Pang H, Lu Q, Gao F (2011) Graphene oxide induced growth of one-dimensional fusiform zirconia nanostructures for highly selective capture of phosphopeptides. Chem Commun (Camb) 47:11772–4

    Google Scholar 

  82. Ambrosi A, Pumera M (2013) Precise tuning of surface composition and electron‐transfer properties of graphene oxide films through electroreduction. Chem Eur J 19:4748–4753

    Google Scholar 

  83. Cui J, Lai Y, Wang W, Li H, Ma X, Zhan J (2014) Galvanic displacement induced reduction of graphene oxide. Carbon 66:738–741

    Google Scholar 

  84. Fan Z, Wang K, Wei T, Yan J, Song L, Shao B (2011) An environmentally friendly and efficient route for the reduction of graphene oxide by aluminum powder. Carbon 48:1686–1689

    Google Scholar 

  85. Mei X, Ouyang J (2011) Ultrasonication-assisted ultrafast reduction of graphene oxide by zinc powder at room temperature. Carbon 49:5389–5397

    Google Scholar 

  86. Wang G, Yang J, Park J, Gou X, Wang B, Liu H, Yao J (2008) Facile synthesis and characterization of graphene nanosheets. J Phys Chem C 112:8192–8195

    Google Scholar 

  87. Wu ZS, Ren WC, Gao LB, Liu BL, Jiang CB, Cheng HM (2009) Synthesis of high-quality graphene with a pre-determined number of layers. Carbon 47:493–499

    Google Scholar 

  88. Li CC, Yu H, Yan Q, Hng HH (2015) Green synthesis of highly reduced graphene oxide by compressed hydrogen gas towards energy storage devices. J Power Sources 274:310–317

    Google Scholar 

  89. Matsumoto Y, Koinuma M, Ida S, Hayami S, Taniguchi T, Hatakeyama K, Tateishi H, Watanabe Y, Amano S (2011) Photoreaction of graphene oxide nanosheets in water. J Phys Chem C 115:19280–19286

    Google Scholar 

  90. Williams G, Seger B, Kamat PV (2008) TiO2-graphene nanocomposites. UV-Assisted photocatalytic reduction of graphene oxide. ACS Nano 2:1487–1491

    Google Scholar 

  91. Ji T, Hua Y, Sun M, Ma N (2013) The mechanism of the reaction of graphite oxide to reduced graphene oxide under ultraviolet irradiation. Carbon 54:412–418

    Google Scholar 

  92. Prezioso S, Perrozzi F, Donarelli M, Stagnini E, Treossi E, Palermo V, Santucci S, Nardone M, Moras P, Ottaviano L (2014) Dose and wavelength dependent study of graphene oxide photoreduction with VUV synchrotron radiation. Carbon 79:478–485

    Google Scholar 

  93. Cote LJ, Cruz-Silva R, Huang JX (2009) Flash reduction and patterning of graphite oxide and its polymer composite. J Am Chem Soc 131:11027–11032

    Google Scholar 

  94. Le Borgne V, Bazi H, Hayashi T, Kim YA, Endo M, El Khakani MA (2014) Hydrogen-assisted pulsed KrF-laser irradiation for the in situ photoreduction of graphene oxide films. Carbon 77:857–867

    Google Scholar 

  95. Trusovas R, Ratautas K, Račiukaitis G, Barkauskas J, Stankevičienė I, Niaura G, Mažeikienė R (2013) Reduction of graphite oxide to graphene with laser irradiation. Carbon 52:574–582

    Google Scholar 

  96. Huang L, Liu Y, Ji L-C, Xie Y-Q, Wang T, Shi W-Z (2011) Pulsed laser assisted reduction of graphene oxide. Carbon 49:2431–2436

    Google Scholar 

  97. Dumée LF, Feng C, He L, Yi Z, She F, Peng Z, Gao W, Banos C, Davies JB, Huynh C (2014) Single step preparation of meso-porous and reduced graphene oxide by gamma-ray irradiation in gaseous phase. Carbon 70:313–318

    Google Scholar 

  98. Zhang Y, Li D, Tan X, Zhang B, Ruan X, Liu H, Pan C, Liao L, Zhai T, Bando Y (2013) High quality graphene sheets from graphene oxide by hot-pressing. Carbon 54:143–148

    Google Scholar 

  99. Chang DW, Choi H-J, Jeon I-Y, Seo J-M, Dai L, Baek J-B (2014) Solvent-free mechanochemical reduction of graphene oxide. Carbon 77:501–507

    Google Scholar 

  100. Eigler S, Dotzer C, Hirsch A (2012) Visualization of defect densities in reduced graphene oxide. Carbon 50:3666–3673

    Google Scholar 

  101. Berger C, Song Z, Li X, Wu X, Brown N, Naud C, Mayou D, Li T, Hass J, Marchenkov AN, Conrad EH, First PN, de Heer WA (2006) Electronic confinement and coherence in patterned epitaxial graphene. Science 312:1191–1196

    Google Scholar 

  102. Behera SK (2011) Enhanced rate performance and cyclic stability of Fe(3)O(4)-graphene nanocomposites for Li ion battery anodes. Chem Commun 47:10371–10373

    Google Scholar 

  103. Boukhvalov DW, Katsnelson MI (2008) Modeling of graphite oxide. J Am Chem Soc 130:10697–10701

    Google Scholar 

  104. Gao X, Jang J, Nagase S (2009) Hydrazine and thermal reduction of graphene oxide: reaction mechanisms, product structures, and reaction design. J Phys Chem C 114:832–842

    Google Scholar 

  105. Kim MC, Hwang GS, Ruoff RS (2009) Epoxide reduction with hydrazine on graphene: a first principles study. J Chem Phys 131:064704

    Google Scholar 

  106. Dreyer DR, Todd AD, Bielawski CW (2014) Harnessing the chemistry of graphene oxide. Chem Soc Rev 43:5288–5301

    Google Scholar 

  107. Tang X-Z, Li W, Yu Z-Z, Rafiee MA, Rafiee J, Yavari F, Koratkar N (2011) Enhanced thermal stability in graphene oxide covalently functionalized with 2-amino-4, 6-didodecylamino-1, 3, 5-triazine. Carbon 49:1258–1265

    Google Scholar 

  108. Liu ZB, Xu YF, Zhang XY, Zhang XL, Chen YS, Tian JG (2009) Porphyrin and fullerene covalently functionalized graphene hybrid materials with large nonlinear optical properties. J Phys Chem B 113:9681–9686

    Google Scholar 

  109. Niyogi S, Bekyarova E, Itkis ME, McWilliams JL, Hamon MA, Haddon RC (2006) Solution properties of graphite and graphene. J Am Chem Soc 128:7720–7721

    Google Scholar 

  110. Xu YF, Liu ZB, Zhang XL, Wang Y, Tian JG, Huang Y, Ma YF, Zhang XY, Chen YS (2009) A graphene hybrid material covalently functionalized with porphyrin: synthesis and optical limiting property. Adv Mater 21:1275–1279

    Google Scholar 

  111. Akhavan O, Ghaderi E (2010) Toxicity of graphene and graphene oxide nanowalls against bacteria. ACS Nano 4:5731–5736

    Google Scholar 

  112. Zhang YJ, Hu WB, Li B, Peng C, Fan CH, Huang Q (2011) Synthesis of polymer-protected graphene by solvent-assisted thermal reduction process. Nanotechnology 22

    Google Scholar 

  113. Zhu J, Li Y, Chen Y, Wang J, Zhang B, Zhang J, Blau WJ (2011) Graphene oxide covalently functionalized with zinc phthalocyanine for broadband optical limiting. Carbon 49:1900–1905

    Google Scholar 

  114. Hu X, Mu L, Wen J, Zhou Q (2012) Covalently synthesized graphene oxide-aptamer nanosheets for efficient visible-light photocatalysis of nucleic acids and proteins of viruses. Carbon 50:2772–2781

    Google Scholar 

  115. Mejias Carpio IE, Mangadlao JD, Nguyen HN, Advincula RC, Rodrigues DF (2014) Graphene oxide functionalized with ethylenediamine triacetic acid for heavy metal adsorption and anti-microbial applications. Carbon 77:289–301

    Google Scholar 

  116. Wu H, Shi H, Wang Y, Jia X, Tang C, Zhang J, Yang S (2014) Hyaluronic acid conjugated graphene oxide for targeted drug delivery. Carbon 69:379–389

    Google Scholar 

  117. Li Z-F, Zhang H, Liu Q, Liu Y, Stanciu L, Xie J (2014) Covalently-grafted polyaniline on graphene oxide sheets for high performance electrochemical supercapacitors. Carbon 71:257–267

    Google Scholar 

  118. Veca LM, Lu FS, Meziani MJ, Cao L, Zhang PY, Qi G, Qu LW, Shrestha M, Sun YP (2009) Polymer functionalization and solubilization of carbon nanosheets. Chem Commun 2565–2567

    Google Scholar 

  119. Yang YF, Wang J, Zhang J, Liu JC, Yang XL, Zhao HY (2009) Exfoliated graphite oxide decorated by PDMAEMA chains and polymer particles. Langmuir 25:11808–11814

    Google Scholar 

  120. Wan Y-J, Tang L-C, Gong L-X, Yan D, Li Y-B, Wu L-B, Jiang J-X, Lai G-Q (2014) Grafting of epoxy chains onto graphene oxide for epoxy composites with improved mechanical and thermal properties. Carbon 69:467–480

    Google Scholar 

  121. Dreyer DR, Jarvis KA, Ferreira PJ, Bielawski CW (2011) Graphite oxide as a dehydrative polymerization catalyst: a one-step synthesis of carbon-reinforced poly(phenylene methylene) composites. Macromolecules 44:7659–7667

    Google Scholar 

  122. Eda G, Mattevi C, Yamaguchi H, Kim H, Chhowalla M (2009) Insulator to semimetal transition in graphene oxide. J Phys Chem C 113:15768–15771

    Google Scholar 

  123. Liu J, Chen G, Jiang M (2011) Supramolecular hybrid hydrogels from noncovalently functionalized graphene with block copolymers. Macromolecules 44:7682–7691

    Google Scholar 

  124. Krueger M, Berg S, Stone DA, Strelcov E, Dikin DA, Kim J, Cote LJ, Huang J, Kolmakov A (2011) Drop-casted self-assembling graphene oxide membranes for scanning electron microscopy on wet and dense gaseous samples. ACS Nano 5:10047–10054

    Google Scholar 

  125. Hu HT, Wang XB, Wang JC, Liu FM, Zhang M, Xu CH (2011) Microwave-assisted covalent modification of graphene nanosheets with chitosan and its electrorheological characteristics. Appl Surf Sci 257:2637–2642

    Google Scholar 

  126. Park S, Dikin DA, Nguyen ST, Ruoff RS (2009) Graphene oxide sheets chemically cross-linked by polyallylamine. J Phys Chem C 113:15801–15804

    Google Scholar 

  127. An Z, Compton OC, Putz KW, Brinson LC, Nguyen ST (2011) Bio‐inspired borate cross‐linking in ultra‐stiff graphene oxide thin films. Adv Mater 23:3842–3846

    Google Scholar 

  128. Gonçalves G, Marques PAAP, Barros-Timmons A, Bdkin I, Singh MK, Emami N, Grácio J (2010) Graphene oxide modified with PMMA via ATRP as a reinforcement filler. J Mater Chem 20:9927–9934

    Google Scholar 

  129. McGrail BT, Rodier BJ, Pentzer E (2014) Rapid functionalization of graphene oxide in water. Chem Mater 26:5806–5811

    Google Scholar 

  130. Eigler S, Hu Y, Ishii Y, Hirsch A (2013) Controlled functionalization of graphene oxide with sodium azide. Nanoscale 5:12136–12139

    Google Scholar 

  131. Kamada S, Nomoto H, Fukuda K, Fukawa T, Shirai H, Kimura M (2011) Noncovalent wrapping of chemically modified graphene with pi-conjugated disk-like molecules. Colloid Polym Sci 289:925–932

    Google Scholar 

  132. Lomeda JR, Doyle CD, Kosynkin DV, Hwang WF, Tour JM (2008) Diazonium functionalization of surfactant-wrapped chemically converted graphene sheets. J Am Chem Soc 130:16201–16206

    Google Scholar 

  133. Gao W, Majumder M, Alemany LB, Narayanan TN, Ibarra MA, Pradhan BK, Ajayan PM (2011) Engineered graphite oxide materials for application in water purification. Acs Appl Mater Inter 3:1821–1826

    Google Scholar 

  134. Ballesteros-Garrido R, Rodriguez R, Álvaro M, Garcia H (2014) Photochemistry of covalently functionalized graphene oxide with phenothiazinyl units. Carbon 74:113–119

    Google Scholar 

  135. Liu F, Chung S, Oh G, Seo TS (2011) Three-dimensional graphene oxide nanostructure for fast and efficient water-soluble dye removal. Acs Appl Mater Inter 4:922–927

    Google Scholar 

  136. Liang J, Huang Y, Zhang L, Wang Y, Ma Y, Guo T, Chen Y (2009) Molecular‐level dispersion of graphene into poly (vinyl alcohol) and effective reinforcement of their nanocomposites. Adv Funct Mater 19:2297–2302

    Google Scholar 

  137. Hu K, Gupta MK, Kulkarni DD, Tsukruk VV (2013) Ultra-robust graphene oxide-silk fibroin nanocomposite membranes. Adv Mater 25:2301–2307

    Google Scholar 

  138. An SJ, Zhu YW, Lee SH, Stoller MD, Emilsson T, Park S, Velamakanni A, An JH, Ruoff RS (2010) Thin film fabrication and simultaneous anodic reduction of deposited graphene oxide platelets by electrophoretic deposition. J Phys Chem Lett 1:1259–1263

    Google Scholar 

  139. Layek RK, Das AK, Park MJ, Kim NH, Lee JH (2015) Enhancement of physical, mechanical, and gas barrier properties in noncovalently functionalized graphene oxide/poly (vinylidene fluoride) composites. Carbon 81:329–338

    Google Scholar 

  140. Bai H, Xu Y, Zhao L, Li C, Shi G (2009) Non-covalent functionalization of graphene sheets by sulfonated polyaniline. Chem Commun 1667–1669

    Google Scholar 

  141. Teng C-C, Ma C-CM LC-H, Yang S-Y, Lee S-H, Hsiao M-C, Yen M-Y, Chiou K-C, Lee T-M (2011) Thermal conductivity and structure of non-covalent functionalized graphene/epoxy composites. Carbon 49:5107–5116

    Google Scholar 

  142. Paci JT, Belytschko T, Schatz GC (2007) Computational studies of the structure, behavior upon heating, and mechanical properties of graphite oxide. J Phys Chem C 111:18099–18111

    Google Scholar 

  143. Satti A, Larpent P, Gun’ko Y (2010) Improvement of mechanical properties of graphene oxide/poly (allylamine) composites by chemical crosslinking. Carbon 48:3376–3381

    Google Scholar 

  144. Li YQ, Yu T, Yang TY, Zheng LX, Liao K (2012) Bio‐inspired nacre‐like composite films based on graphene with superior mechanical, electrical, and biocompatible properties. Adv Mater 24:3426–3431

    Google Scholar 

  145. Cheng Q, Wu M, Li M, Jiang L, Tang Z (2013) Ultratough artificial nacre based on conjugated cross‐linked graphene oxide. Angew Chem Int Ed 125:3838–3843

    Google Scholar 

  146. Tian Y, Cao Y, Wang Y, Yang W, Feng J (2013) Realizing ultrahigh modulus and high strength of macroscopic graphene oxide papers through crosslinking of mussel‐inspired polymers. Adv Mater 25:2980–2983

    Google Scholar 

  147. Hu H, Brown PH, Labavitch JM (1996) Species variability in boron requirement is correlated with cell wall pectin. J Exp Bot 47:227–232

    Google Scholar 

  148. Sudeep PM, Narayanan TN, Ganesan A, Shaijumon MM, Yang H, Ozden S, Patra PK, Pasquali M, Vajtai R, Ganguli S, Roy AK, Anantharaman MR, Ajayan PM (2013) Covalently interconnected three-dimensional graphene oxide solids. ACS Nano 7:7034–7040

    Google Scholar 

  149. Wei W, Yang S, Zhou H, Lieberwirth I, Feng X, Müllen K (2013) 3D graphene foams cross‐linked with pre‐encapsulated Fe3O4 nanospheres for enhanced lithium storage. Adv Mater 25:2909–2914

    Google Scholar 

  150. Wan W, Li L, Zhao Z, Hu H, Hao X, Winkler DA, Xi L, Hughes TC, Qiu J (2014) Ultrafast fabrication of covalently cross‐linked multifunctional graphene oxide monoliths. Adv. Funct, Mater

    Google Scholar 

  151. Sun H, Xu Z, Gao C (2013) Synergistically assembled carbon aerogels. Adv Mater 25:2554–2560

    Google Scholar 

  152. Huang H, Chen P, Zhang X, Lu Y, Zhan W (2013) Edge‐to‐edge assembled graphene oxide aerogels with outstanding mechanical performance and superhigh chemical activity. Small 9:1397–1404

    Google Scholar 

  153. Hu H, Zhao Z, Wan W, Gogotsi Y, Qiu J (2013) Ultralight and highly compressible graphene aerogels. Adv Mater 25:2219–2223

    Google Scholar 

  154. Yang X, Qiu L, Cheng C, Wu Y, Ma ZF, Li D (2011) Ordered gelation of chemically converted graphene for next‐generation electroconductive hydrogel films. Angew Chem Int Ed 50:7325–7328

    Google Scholar 

  155. Cong HP, Wang P, Yu SH (2014) Highly elastic and superstretchable graphene oxide/polyacrylamide hydrogels. Small 10:448–453

    Google Scholar 

  156. Wu L, Ohtani M, Takata M, Saeki A, Seki S, Ishida Y, Aida T (2014) Magnetically induced anisotropic orientation of graphene oxide locked by in situ hydrogelation. ACS Nano 8(5):4640–9

    Google Scholar 

  157. Compton OC, Cranford SW, Putz KW, An Z, Brinson LC, Buehler MJ, Nguyen ST (2012) Tuning the mechanical properties of graphene oxide paper and its associated polymer nanocomposites by controlling cooperative intersheet hydrogen bonding. ACS Nano 6:2008–2019

    Google Scholar 

  158. Arndt KF (2006) Hydrogel sensors and actuators. Frontiers 4

    Google Scholar 

  159. Zhang H, Kuila T, Kim NH, Yu DS, Lee JH (2014) Simultaneous reduction, exfoliation, and nitrogen doping of graphene oxide via a hydrothermal reaction for energy storage electrode materials. Carbon 69:66–78

    Google Scholar 

  160. Van Khai T, Na HG, Kwak DS, Kwon YJ, Ham H, Shim KB, Kim HW (2012) Influence of N-doping on the structural and photoluminescence properties of graphene oxide films. Carbon 50:3799–3806

    Google Scholar 

  161. Li M, Wu Z, Ren W, Cheng H, Tang N, Wu W, Zhong W, Du Y (2012) The doping of reduced graphene oxide with nitrogen and its effect on the quenching of the material’s photoluminescence. Carbon 50:5286–5291

    Google Scholar 

  162. Liu Y, Feng Q, Tang N, Wan X, Liu F, Lv L, Du Y (2013) Increased magnetization of reduced graphene oxide by nitrogen-doping. Carbon 60:549–551

    Google Scholar 

  163. Liu Y, Feng Q, Xu Q, Li M, Tang N, Du Y (2013) Synthesis and photoluminescence of F and N co-doped reduced graphene oxide. Carbon 61:436–440

    Google Scholar 

  164. Yang J, Jo MR, Kang M, Huh YS, Jung H, Kang Y-M (2014) Rapid and controllable synthesis of nitrogen doped reduced graphene oxide using microwave-assisted hydrothermal reaction for high power-density supercapacitors. Carbon 73:106–113

    Google Scholar 

  165. Yang S, Zhi L, Tang K, Feng X, Maier J, Müllen K (2012) Efficient synthesis of heteroatom (N or S)-doped graphene based on ultrathin graphene oxide-porous silica sheets for oxygen reduction reactions. Adv Funct Mater 22:3634–3640

    Google Scholar 

  166. Chen S, Chen P, Wang Y (2011) Carbon nanotubes grown in situ on graphene nanosheets as superior anodes for Li-ion batteries. Nanoscale 3:4323–4329

    Google Scholar 

  167. Wang K, Ruan J, Song H, Zhang JL, Wo Y, Guo SW, Cui DX (2013) Biocompatibility of graphene oxide. Nanoscale Res Lett 8(1):393

    Google Scholar 

  168. Liao KH, Lin YS, Macosko CW, Haynes CL (2011) Cytotoxicity of graphene oxide and graphene in human erythrocytes and skin fibroblasts. Acs Appl Mater Inter 3:2607–2615

    Google Scholar 

  169. Wojtoniszak M, Chen X, Kalenczuk RJ, Wajda A, Lapczuk J, Kurzewski M, Drozdzik M, Chu PK, Borowiak-Palen E (2012) Synthesis, dispersion, and cytocompatibility of graphene oxide and reduced graphene oxide. Colloids Surf B Biointerfaces 89:79–85

    Google Scholar 

  170. Begurn P, Ikhtiari R, Fugetsu B (2011) Graphene phytotoxicity in the seedling stage of cabbage, tomato, red spinach, and lettuce. Carbon 49:3907–3919

    Google Scholar 

  171. Pan DY, Wang S, Zhao B, Wu MH, Zhang HJ, Wang Y, Jiao Z (2009) Li storage properties of disordered graphene nanosheets. Chem Mater 21:3136–3142

    Google Scholar 

  172. Sun XM, Liu Z, Welsher K, Robinson JT, Goodwin A, Zaric S, Dai HJ (2008) Nano-graphene oxide for cellular imaging and drug delivery. Nano Res 1:203–212

    Google Scholar 

  173. Agarwal S, Zhou XZ, Ye F, He QY, Chen GCK, Soo J, Boey F, Zhang H, Chen P (2010) Interfacing live cells with nanocarbon substrates. Langmuir 26:2244–2247, http://pubs.rsc.org/en/content/articlehtml/2010/jm/c0jm01674h

  174. Chang YL, Yang ST, Liu JH, Dong E, Wang YW, Cao AN, Liu YF, Wang HF (2011) In vitro toxicity evaluation of graphene oxide on A549 cells. Toxicol Lett 200:201–210

    Google Scholar 

  175. Ryoo SR, Kim YK, Kim MH, Min DH (2010) Behaviors of NIH-3 T3 fibroblasts on graphene/carbon nanotubes: proliferation, focal adhesion, and gene transfection studies. ACS Nano 4:6587–6598

    Google Scholar 

  176. Park S, Mohanty N, Suk JW, Nagaraja A, An JH, Piner RD, Cai WW, Dreyer DR, Berry V, Ruoff RS (2010) Biocompatible, robust free-standing paper composed of a TWEEN/graphene composite. Adv Mater 22:1736–40

    Google Scholar 

  177. Chen H, Muller MB, Gilmore KJ, Wallace GG, Li D (2008) Mechanically strong, electrically conductive, and biocompatible graphene paper. Adv Mater 20:3557–61

    Google Scholar 

  178. Ruiz ON, Fernando KAS, Wang BJ, Brown NA, Luo PG, McNamara ND, Vangsness M, Sun YP, Bunker CE (2011) Graphene oxide: a nonspecific enhancer of cellular growth. ACS Nano 5:8100–8107

    Google Scholar 

  179. Bao Q, Zhang D, Qi P (2011) Synthesis and characterization of silver nanoparticle and graphene oxide nanosheet composites as a bactericidal agent for water disinfection. J Colloid Interface Sci 360:463–470

    Google Scholar 

  180. Das MR, Sarma RK, Saikia R, Kale VS, Shelke MV, Sengupta P (2011) Synthesis of silver nanoparticles in an aqueous suspension of graphene oxide sheets and its antimicrobial activity. Coll Surf B Biointerf 83:16–22

    Google Scholar 

  181. Dikin DA, Stankovich S, Zimney EJ, Piner RD, Dommett GHB, Evmenenko G, Nguyen ST, Ruoff RS (2007) Preparation and characterization of graphene oxide paper. Nature 448:457–460

    Google Scholar 

  182. Buchsteiner A, Lerf A, Pieper J (2006) Water dynamics in graphite oxide investigated with neutron scattering. J Phys Chem B 110:22328–22338

    Google Scholar 

  183. Lerf A, Buchsteiner A, Pieper J, Sch枚ttl S, Dekany I, Szabo T, Boehm HP (2006) Hydration behavior and dynamics of water molecules in graphite oxide. J Phys Chem Solid 67:1106–1110

    Google Scholar 

  184. Jung I, Dikin D, Park S, Cai W, Mielke SL, Ruoff RS (2008) Effect of water vapor on electrical properties of individual reduced graphene oxide sheets. J Phys Chem C 112:20264–20268

    Google Scholar 

  185. Medhekar NV, Ramasubramaniam A, Ruoff RS, Shenoy VB (2010) Hydrogen bond networks in graphene oxide composite paper: structure and mechanical properties. ACS Nano 4:2300–2306

    Google Scholar 

  186. Acik M, Mattevi C, Gong C, Lee G, Cho K, Chhowalla M, Chabal YJ (2010) The role of intercalated water in multilayered graphene oxide. ACS Nano 4:5861–5868

    Google Scholar 

  187. Song L, Khoerunnisa F, Gao W, Dou W, Hayashi T, Kaneko K, Endo M, Ajayan PM (2013) Effect of high-temperature thermal treatment on the structure and adsorption properties of reduced graphene oxide. Carbon 52:608–612

    Google Scholar 

  188. Gao W, Singh N, Song L, Liu Z, Reddy ALM, Ci LJ, Vajtai R, Zhang Q, Wei BQ, Ajayan PM (2011) Direct laser writing of micro-supercapacitors on hydrated graphite oxide films. Nat Nanotechnol 6:496–500

    Google Scholar 

  189. Gao W, Wu G, Janicke MT, Cullen DA, Mukundan R, Baldwin JK, Brosha EL, Galande C, Ajayan PM, More KL (2014) Ozonated graphene oxide film as a proton‐exchange membrane. Angew Chem Int Ed 53:3588–3593

    Google Scholar 

  190. Karim MR, Hatakeyama K, Matsui T, Takehira H, Taniguchi T, Koinuma M, Matsumoto Y, Akutagawa T, Nakamura T, Noro S-I (2013) Graphene oxide nanosheet with high proton conductivity. J Am Chem Soc 135:8097–8100

    Google Scholar 

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Acknowledgement

W. G. sincerely thank for the start-up funding support from the Department of Textile Engineering, Chemistry and Science at North Carolina State University, Raleigh, NC.

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Gao, W. (2015). The Chemistry of Graphene Oxide. In: Gao, W. (eds) Graphene Oxide. Springer, Cham. https://doi.org/10.1007/978-3-319-15500-5_3

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