Preparation of efficient magnetic biosorbents by clicking carbohydrates onto graphene oxide
Source abstract
Abstract
In this work, hydrophilic graphene nanosheets (GNS) and the related magnetic nanocomposites were prepared by first tethering alkyne-functionalized graphene oxide (GO) with azide-modified glucose followed by deposition of Fe3O4 nanoparticles on the functionalized GNS. For the preparation of nanohybrids, two approaches were designed: in the first one, after chlorination of GO with thionyl chloride, GO was reacted with propargyl alcohol and subsequently clicked with azide-glucoside. The resulted sweet GNS were easily dispersed in water and stable for 2 weeks. In the second approach, GO was functionalized with 3,4,5-tris(prop-2-yn-1-yloxy)benzoic acid via hydroxyl groups on its basal plane and finally treated with azide-glucoside. The obtained hydrophilic GNS were stable in water for 3 weeks. The results showed that both glucose-grafted GO sheets were reduced by sodium ascorbate during click-coupling reaction; this is one of the many advantages of click reaction. Finally, Fe3O4 nanoparticles were deposited on the sweet GNS and were superparamagnetic, responded quickly to an external magnetic field and exhibited efficient adsorption towards methylene blue, as a cationic dye. No leaching was observed even after a week of placing a magnet close to the vial containing the dispersion of magnetic sweet GNS.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Graphene and Nanomaterials Applications · Graphene research and applications · Nanomaterials for catalytic reactions
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (75)
Show source-provided references
1. Novoselov KS, Geim AK, Morozov SV, Jiang D, Zhang Y, Dubonos SV (2004) Electric field effect in atomically thin carbon films. Science 306:666–66910.1126/science.1102896 ↗
2. Liao L, Lin Y-C, Bao M, Cheng R, Bai J, Liu Y (2010) High-speed graphene transistors with a self-aligned nanowire gate. Nature 467:305–30810.1038/nature09405 ↗
3. Balandin AA, Ghosh S, Bao W, Calizo I, Teweldebrhan D, Miao F (2008) Macroscopic graphene membranes and their extraordinary stiffness. Nano Lett 8:902–90710.1021/nl0731872 ↗
4. Chen C, Rosenblatt S, Bolotin KI, Kalb W, Kim P, Kymissis I (2009) Performance of monolayer graphene nanomechanical resonators with electrical readout. Nat Nanotechnol 4:861–86710.1038/nnano.2009.267 ↗
5. Mueller T, Xia F, Avouris P (2010) Graphene photodetectors for high-speed optical communications. Nat Photonics 4:297–30110.1038/nphoton.2010.40 ↗
6. Bonaccorso F, Sun Z, Hasan T, Ferrari AC (2010) Graphene photonics and optoelectronics. Nat Photonics 4:611–62210.1038/nphoton.2010.186 ↗
7. Ratinac KR, Yang W, Ringer SP, Braet F (2010) Toward ubiquitous environmental gas sensors-capitalizing on the promise of graphene. Environ Sci Technol 44:1167–117610.1021/es902659d ↗
8. Dan Y, Lu Y, Kybert NJ, Luo Z, Johnson ATC (2009) Intrinsic response of graphene vapor sensors. Nano Lett 9:1472–147510.1021/nl8033637 ↗
9. Schedin F, Geim AK, Morozov SV, Hill EW, Blake P, Katsnelson MI (2007) Detection of individual gas molecules adsorbed on graphene. Nat Mater 6:652–65510.1038/nmat1967 ↗
10. Liu Y, Yu D, Zeng C, Miao Z, Dai L (2010) Biocompatible graphene oxide-based glucose biosensors. Langmuir 26:6158–616010.1021/la100886x ↗
11. Georgakilas V, Otyepka M, Bourlinos AB, Chandra V, Kim N, Kemp KC (2012) Functionalization of graphene: covalent and non-covalent approaches, derivatives and applications. Chem Rev 112:6156–621410.1021/cr3000412 ↗
12. Choi EY, Han TH, Hong J, Kim JE, Lee SH, Kim HW (2010) Noncovalent functionalization of graphene with end-functional polymers. J Mater Chem 20:1907–191210.1039/b919074k ↗
13. Yang Q, Pan X, Huang F, Li K (2010) Fabrication of high-concentration and stable aqueous suspensions of graphene nanosheets by noncovalent functionalization with lignin and cellulose derivatives. J Phys Chem C 114:3811–381610.1021/jp910232x ↗
14. Sharma R, Baik JH, Perera CJ, Strano MS (2010) Anomalously large reactivity of single graphene layers and edges toward electron transfer chemistries. Nano Lett 10:398–40510.1021/nl902741x ↗
15. Loh KP, Bao Q, Ang PK, Yang J (2010) The chemistry of graphene. J Mater Chem 20:2277–228910.1039/b920539j ↗
16. Dreyer DR, Park S, Bielawski CW, Ruoff RS (2010) The chemistry of graphene oxide. Chem Soc Rev 39:228–24010.1039/B917103G ↗
17. Compton OC, Dikin DA, Putz KW, Brinson LC, Nguyen ST (2010) Electrically conductive “alkylated” graphene paper via chemical reduction of amine-functionalized graphene oxide paper. Adv Mater 22:892–89610.1002/adma.200902069 ↗
18. Meng F, Ishida H, Liu X (2014) Introduction of benzoxazine onto the graphene oxide surface by click chemistry and the properties of graphene oxide reinforced polybenzoxazine nanohybrids. RSC Adv 4:9471–947510.1039/c3ra47345g ↗
19. Zhang X, Browne WR, Feringa BL (2012) Preparation of dispersible graphene through organic functionalization of graphene using a zwitterion intermediate cycloaddition approach. RSC Adv 2:12173–1217610.1039/c2ra22440b ↗
20. Veca LM, Lu FS, Meziani MJ, Cao L, Zhang PY, Qi G (2009) Polymer functionalization and solubilization of carbon nanosheets. Chem Commun 18:2565–256710.1039/b900590k ↗
21. Shen J, Hu Y, Li C, Qin C, Ye M (2009) Synthesis of amphiphilic graphene nanoplatelets. Small 5:82–8510.1002/smll.200800988 ↗
22. Chen Y, Zhang X, Yu P, Ma Y (2009) Stable dispersions of graphene and highly conducting graphene films: a new approach to creating colloids of graphene monolayers. Chem Commun 30:4527–452910.1039/b907723e ↗
23. Chandra V, Park J, Chun Y, Lee WJ, Hwang IC, Kim KS (2010) Water-dispersible magnetite-reduced graphene oxide composites for arsenic removal. ACS Nano 4:3979–398610.1021/nn1008897 ↗
24. Yang H, Shan C, Li F, Han D, Zhang Q, Niu L (2009) Covalent functionalization of polydisperse chemically-converted graphene sheets with amine-terminated ionic liquid. Chem Commun 26:3880–388210.1039/b905085j ↗
25. Yang Q, Pan X, Clarke K, Li K (2012) Covalent functionalization of graphene with polysaccharides. Ind Eng Chem Res 51:310–31710.1021/ie201391e ↗
26. Kolb HC, Finn MG, Sharpless KB (2004) Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed 40:2004–202110.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5 ↗
27. Golas PL, Matyjaszewski K (2010) Marrying click chemistry with polymerization: expanding the scope of polymeric materials. Chem Soc Rev 39:1338–135410.1039/B901978M ↗
28. Li N, Binder WH (2011) Click-chemistry for nanoparticle-modification. J Mater Chem 21:16717–1673410.1039/c1jm11558h ↗
29. Franc G, Kakkar AK (2010) ‘‘Click’’ methodologies: efficient, simple and greener routes to design dendrimers. Chem Soc Rev 39:1536–154410.1039/b913281n ↗
30. Millward SW, Agnew HD, Lai B, Lee SS, Lim J, Nag A (2013) In situ click chemistry: from small molecule discovery to synthetic antibodies. Integr Biol 5:87–9510.1039/C2IB20110K ↗
31. Thirumurugan P, Matosiuk D, Jozwiak K (2013) Click chemistry for drug development and diverse chemical–biology applications. Chem Rev 113:4905–497910.1021/cr200409f ↗
32. Xi W, Scott TF, Kloxin CJ, Bowman CN (2014) Click chemistry in materials science. Adv Func Mater 24:2572–259010.1002/adfm.201302847 ↗
33. Pieters RJ, Rijkers DTS, Liskamp RMJ (2007) Application of the 1,3-dipolar cycloaddition reaction in chemical biology: approaches toward multivalent carbohydrates and peptides and peptide-based polymers. QSAR Comb Sci 26:1181–119010.1002/qsar.200740075 ↗
34. Chen Y, Star A, Vidal S (2013) Sweet carbon nanostructures: carbohydrate conjugates with carbon nanotubes and graphene and their applications. Chem Soc Rev 42:4532–454210.1039/C2CS35396B ↗
35. Ryu HJ, Mahapatra SS, Yadav SK, Cho JW (2012) Synthesis of click-coupled graphene sheet with chitosan: effective exfoliation and enhanced properties of their nanocomposites. Eur Polym J 49:2627–2634
36. Sun S, Cao Y, Feng J, Wu P (2010) Click chemistry as a route for the immobilization of well-defined polystyrene onto graphene sheets. J Mater Chem 20:5605–560710.1039/c0jm01269f ↗
37. Pan Y, Bao H, Sahoo NG, Wu T, Li L (2011) Water-soluble poly(N-isopropylacrylamide)–graphene sheets synthesized via click chemistry for drug delivery. Adv Func Mater 21:2754–276310.1002/adfm.201100078 ↗
38. Cao Y, Lai Z, Feng J, Wu P (2011) Graphene oxide sheets covalently functionalized with block copolymers via click chemistry as reinforcing fillers. J Mater Chem 21:9271–927810.1039/c1jm10420a ↗
39. Yang H, Kwon Y, Kwon T, Lee H, Kim BJ (2012) ‘Click’ preparation of CuPt nanorod-anchored graphene oxide as a catalyst in water. Small 8:3161–316810.1002/smll.201201002 ↗
40. Yadav SK, Yoo HJ, Cho JW (2013) Click coupled graphene for fabrication of high-performance polymer nanocomposites. J Polym Sci B 51:39–4710.1002/polb.23155 ↗
41. Devadoss A, Chidsey CED (2007) Azide-modified graphitic surfaces for covalent attachment of alkyne-terminated molecules by “click” chemistry. J Am Chem Soc 129:5370–537110.1021/ja071291f ↗
42. Zhang W, Shi X, Zhang Y, Gu W, Li B, Xian Y (2013) Synthesis of water-soluble magnetic graphene nanocomposites for recyclable removal of heavy metal ions. J Mater Chem A 1:1745–175310.1039/C2TA00294A ↗
43. Bustos-Ramírez K, Martínez-Hernández AL, Martínez-Barrera G, de Icaza M, Castaño VM, Velasco-Santos C (2013) Covalently bonded chitosan on graphene oxide via redox reaction. Materials 6:911–92610.3390/ma6030911 ↗
44. Kabiri R, Namazi H (2014) Surface grafting of reduced graphene oxide using nanocrystalline cellulose via click reaction. J Nanopart Res 16:2474–247810.1007/s11051-014-2474-3 ↗
45. Namvari M, Namazi H (2014) Sweet graphene I: fabrication of water- soluble graphene nanosheets by covalently attaching alkyne- terminated saccharides onto azide- modified graphene oxide by “click” chemistry. Carbohydr Res 396:1–810.1016/j.carres.2014.06.012 ↗
46. Zhang X, Liu X, Zheng W, Zhu J (2012) Regenerated cellulose/graphene nanocomposite films prepared in DMAC/LiCl solution. Carbohydr Polym 88:26–3010.1016/j.carbpol.2011.11.054 ↗
47. Li R, Liu C, Ma M (2011) Studies on the properties of graphene oxide-reinforced starch biocomposites. Carbohyd Polym 84:631–63710.1016/j.carbpol.2010.12.041 ↗
48. Kabiri R, Namazi H (2014) Nanocrystalline cellulose acetate (NCCA)/graphene oxide (GO) nanocomposites with enhanced mechanical properties and barrier against water vapor. Cellulose 21:3527–353910.1007/s10570-014-0366-4 ↗
49. Namvari M, Namazi H (2014) Synthesis of magnetic citric acid-functionalized graphene oxide and its application in the removal of methylene blue from contaminated water. Polym Int 63:1881–188810.1002/pi.4769 ↗
50. Liu L, Li C, Bao C, Jia Q, Xiao P, Liu X (2012) Preparation and characterization of chitosan/graphene oxide composites for the adsorption of Au(III) and Pd(II). Talanta 93:350–35710.1016/j.talanta.2012.02.051 ↗
51. Yu J-G, Zhao X-H, Yang H, Liu Q, Chen X-H, Jiang X-Y, Chen X-Q, Jiao F-P (2014) Aqueous adsorption and removal of organic contaminants by carbon nanotubes. Sci Total Environ 482–483:241–251
52. Yu J-G, Yu L-Y, Yang H, Liu Q, Chen X-H, Jiang X-Y, Chen X-Q, Jiao F-P (2015) Graphene nanosheets as novel adsorbents in adsorption, preconcentration and removal of gases, organic compounds and metal ions. Sci Total Environ 502:70–7910.1016/j.scitotenv.2014.08.077 ↗
53. Kui L, Xia ZG, Ke WX (2012) A brief review of graphene-based material synthesis and its application in environmental pollution management. Chin Sci Bull 57:1223–123410.1007/s11434-012-4986-5 ↗
54. Yao Y, Miao S, Liu S, Ma LP, Sun H, Wang S (2012) Synthesis, characterization, and adsorption properties of magnetic Fe3O4@graphene nanocomposite. Chem Eng J 184:326–33210.1016/j.cej.2011.12.017 ↗
55. Xie G, Xi P, Liu H, Chen F, Huang L, Shi Y, Hou F, Zeng Z, Shao C, Wang J (2012) A facile chemical method to produce superparamagnetic grapheme oxide–Fe3O4 hybrid composite and its application in the removal of dyes from aqueous solution. J Mater Chem 22:1033–103910.1039/C1JM13433G ↗
56. Wang C, Feng C, Gao Y, Ma X, Wu Q, Wang Z (2011) Preparation of a graphene-based magnetic nanocomposite for the removal of an organic dye from aqueous solution. Chem Eng J 173:92–9710.1016/j.cej.2011.07.041 ↗
57. Ai L, Zhang C, Chen Z (2011) Removal of methylene blue from aqueous solution by a solvothermal-synthesized graphene/magnetite composite. J Hazard Mater 192:1515–152410.1016/j.jhazmat.2011.06.068 ↗
58. Geng Z, Lin Y, Yu X, Shen Q, Ma L, Li Z, Pan N, Wang X (2012) Highly efficient dye adsorption and removal: a functional hybrid of reduced graphene oxide–Fe3O4 nanoparticles as an easily regenerative adsorbent. J Mater Chem 22:3527–353510.1039/c2jm15544c ↗
59. Sun H, Cao L, Lu L (2011) Magnetite/reduced graphene oxide nanocomposites: one step solvothermal synthesis and use as a novel platform for removal of dye pollutants. Nano Res 4:550–56210.1007/s12274-011-0111-3 ↗
60. Namvari M, Namazi H (2014) Clicking graphene oxide and Fe3O4 nanoparticles together: an efficient adsorbent to remove dyes from aqueous solutions. Int J Environ Sci Tech 11:1527–153610.1007/s13762-014-0595-y ↗
61. Zhang K, Zhang LL, Zhao XS, Wu J (2012) Graphene/polyaniline nanofiber composites as supercapacitor electrodes. J Chem Mater 22:1392–140110.1021/cm902876u ↗
62. Roy B, Mukhopadhyay (2007) Sulfuric acid immobilized on silica: an excellent catalyst for Fischer type glycosylation. Tetrahedron Lett 48:3783–378710.1016/j.tetlet.2007.03.165 ↗
63. Geng J, Mantovani G, Tao L, Nicolas J, Chen G, Wallis R (2007) Site-directed conjugation of ‘click’ glycopolymers to from glycoprotein mimics: binding to mammalian lectin and induction of immunological function. J Am Chem Soc 129:15156–1516310.1021/ja072999x ↗
64. Dam HH, Caruso F (2012) Modular click assembly of degradable capsules using polyrotaxanes. ACS Nano 6:4686–469310.1021/nn301045z ↗
65. Zhang J, Yang H, Shen G, Cheng P, Zhang J, Guo S (2010) Reduction of graphene oxide via L-ascorbic acid. Chem Commun 46:1112–111410.1039/B917705A ↗
66. Fernandez-Merino MJ, Guardia L, Paredes JI, Villar-Rodil S, SolisFernandez P, Martinez-Alonso A et al (2010) Vitamin C is an ideal substitute for hydrazine in the reduction of graphene oxide suspensions. J Phys Chem C 114:6426–643210.1021/jp100603h ↗
67. Shen J, Shi M, Ma H, Yan B, Li N, Hu Y (2010) Synthesis of hydrophilic and organophilic chemically modified graphene oxide sheets. J Colloid Interface Sci 351:366–37010.1016/j.jcis.2010.08.036 ↗
68. Salvio R, Krabbenborg S, Naber WJM, Velders AH, Reinhoudt DN, van der Wiel WG (2009) The formation of large-area conducting graphene-like platelets. Chem Eur J 15:8235–824010.1002/chem.200900661 ↗
69. Hong RY, Feng B, Liua G, Wang S, Li HZ, Ding JM, Zheng Y, Wei DG (2009) Preparation and characterization of Fe3O4/polystyrene composite particles via inverse emulsion polymerization. J Alloy Compd 476:612–61810.1016/j.jallcom.2008.09.060 ↗
70. Chang PR, Yua J, Maa X, Anderson DP (2011) Polysaccharides as stabilizers for the synthesis of magnetic nanoparticles Carbohydr. Polym. 83:640–644
71. Juang RS, Wu FC, Tseng RL (2000) Mechanism of adsorption of dyes and phenols from water using activated carbons prepared from plum kernels. J Colloid Interface Sci 227:437–44410.1006/jcis.2000.6912 ↗
72. Yang S-T, Chen S, Chang Y, Cao A, Liu Y, Wang H (2011) Removal of methylene blue from aqueous solution by graphene oxide. J Colloid Interface Sci 359:24–2910.1016/j.jcis.2011.02.064 ↗
73. Qu S, Huang F, Yu SN, Chen G, Kong JL (2008) Magnetic removal of dyes from aqueous solution using multi-walled carbon nanotubes filled with Fe2O3 particles. J Hazard Mater 160:643–64710.1016/j.jhazmat.2008.03.037 ↗
74. Thuy-Duong NP, Hung VP, Kim EJ, Oh ES, Hur SH, Chung JS (2012) Reduced graphene oxide–titanate hybrids: morphologic evolution by alkali-solvothermal treatment and applications in water purification. Appl Surf Sci 258:4551–455710.1016/j.apsusc.2012.01.026 ↗
75. Ai L, Jiang J (2012) Removal of methylene blue from aqueous solution with self-assembled cylindrical graphene–carbon nanotube hybrid. Chem Eng J 192:156–16310.1016/j.cej.2012.03.056 ↗