A new graphene oxide (GO)-based hydrogel was synthesized through cross-linking of biofunctionalized graphene oxide nanosheets by di-alkyne polyethylene glycol as cross-linking agent. In this respect, nitrene chemistry as a convenient and straightforward protocol was developed for biofunctionalization of GO using an azido-starch as an eco-friendly, biodegradable and cost-effective material. In the next step, 1,3-dipolar cycloaddition chemistry, a green and highly efficient approach was utilized in cross-linking of functionalized GO by PEG through click reaction between remaining azido groups of starch on the surface of GO sheets and terminal alkyne groups of polyethylene glycol. Formation of aziridine and triazole rings during functionalization and cross-linking in this method could evidently improve biological activities of the obtained hydrogel compared to the conventional methods. The antibacterial activity of the new compounds was explored. The synthesized hydrogel showed antibacterial properties against Gram-positive and Gram-negative bacteria due to the presence of triazole rings. Also, the resulting hydrogel exhibited high dye removal efficiency and it can be utilized in water treatment effectively. The adsorption kinetics was analyzed through the effects of adsorption time and the dye concentration on the adsorption capacity. Kinetic data were accurately described by a pseudo-second-order model.
This is a preview of subscription content, log in to check access.
Buy single article
Instant access to the full article PDF.
Price includes VAT for USA
Subscribe to journal
Immediate online access to all issues from 2019. Subscription will auto renew annually.
This is the net price. Taxes to be calculated in checkout.
He H, Gao C (2010) General approach to individually dispersed, highly soluble, and conductive graphene nanosheets functionalized by nitrene chemistry. Chem Mater 22:5054–5064
Xing R, Wang W, Jiao T, Ma K, Zhang Q, Hong W, Qiu H, Zhou J, Peng Q (2017) Bioinspired polydopamine sheathed nanofibers containing carboxylate graphene oxide nanosheet for high-efficient dyes scavenger. ACS Sustain Chem Eng 5:4948–4956
Liu Y, Hou C, Jiao T, Song J, Zhang X, Xing R, Zhou J, Zhang L, Peng Q (2018) Self-assembled AgNP-containing nanocomposites constructed by electrospinning as efficient dye photocatalyst materials for wastewater treatment. Nanomaterials 8:35
Gul K, Sohni S, Waqar M, Ahmad F, Norulaini NN, AK MO (2016) Functionalization of magnetic chitosan with graphene oxide for removal of cationic and anionic dyes from aqueous solution. Carbohydr Polym 152:520–531
Qi Y, Yang M, Xu W, He S, Men Y (2017) Natural polysaccharides-modified graphene oxide for adsorption of organic dyes from aqueous solutions. J Colloid Interface Sci 486:84–96
Peña-Bahamonde J, San Miguel V, Nguyen HN, Ozisik R, Rodrigues DF, Cabanelas JC (2017) Functionalization of reduced graphene oxide with polysulfone brushes enhance antibacterial properties and reduce human cytotoxicity. Carbon 111:258–268
Tan W, Li Q, Wang H, Liu Y, Zhang J, Dong F, Guo Z (2016) Synthesis, characterization, and antibacterial property of novel starch derivatives with 1, 2, 3-triazole. Carbohydr Polym 142:1–7
Dong F, Zhang J, Yu C, Li Q, Ren J, Wang G, Gu G, Guo Z (2014) Synthesis of amphiphilic aminated inulin via ‘click chemistry’ and evaluation for its antibacterial activity. Bioorg Med Chem Lett 24:4590–4593
Rodrigo AC, Malhotra S, Böttcher C, Adeli M, Haag R (2014) Dendritic polyglycerol cyclodextrin amphiphiles and their self-assembled architectures to transport hydrophobic guest molecules. RSC Adv 4:61656–61659
Salehi P, Babanezhad-Harikandei K, Bararjanian M, Al-Harrasi A, Esmaeili M-A, Aliahmadi A (2016) Synthesis of novel 1,2,3-triazole tethered 1,3-disubstituted β-carboline derivatives and their cytotoxic and antibacterial activities. Med Chem Res 25:1895–1907
Liu J, Zhu K, Jiao T, Xing R, Hong W, Zhang L, Zhang Q, Peng Q (2017) Preparation of graphene oxide–polymer composite hydrogels via thiol-ene photopolymerization as efficient dye adsorbents for wastewater treatment. Colloid Surf A Physicochem Eng Asp 529:668–676
Luo X, Ma K, Jiao T, Xing R, Zhang L, Zhou J, Li B (2017) Graphene oxide–polymer composite Langmuir films constructed by interfacial thiol-ene photopolymerization. Nanoscale Res Lett 12:99
Hummers WS Jr, Offeman RE (1958) Preparation of graphitic oxide. J Am Chem Soc 80:1339–1339
Detrembleur C, Debuigne A, Altintas O, Conradi M, Wong EH, Jérôme C, Barner-Kowollik C, Junkers T (2012) Synthesis of star and H-shape polymers via a combination of cobalt-mediated radical polymerization and nitrone-mediated radical coupling reactions. Polym Chem 3:135–147
Furukawa S, Katayama N, Iizuka T, Urabe I, Okada H (1980) Preparation of polyethylene glycol-bound NAD and its application in a model enzyme reactor. FEBS Lett 121:239–242
Elchinger P-H, Montplaisir D, Zerrouki R (2012) Starch–cellulose crosslinking—towards a new material. Carbohydr Polym 87:1886–1890
Lai J, Yang F, Guo H, Jiao Z (2014) Novel effective dye sorbents: synthesis and properties of 1,2,3-triazole-modified thiacalix  arene polymers based on click chemistry. Iran Polym J 23:899–906
Feng Y, Feng N, Du G (2013) A green reduction of graphene oxide via starch-based materials. RSC Adv 3:21466–21474
Akyüz D, Keskin B, Şahintürk U, Koca A (2016) Electrocatalytic hydrogen evolution reaction on reduced graphene oxide electrode decorated with cobaltphthalocyanine. Appl Catal B 188:217–226
Ambrosi A, Bonanni A, Sofer Z, Cross JS, Pumera M (2011) Electrochemistry at chemically modified graphenes. Chem Eur J 17:10763–10770
Tien HN, Hien NTM, Oh E-S, Chung J, Kim EJ, Choi WM, Kong B-S, Hur SH (2013) Synthesis of a highly conductive and large surface area graphene oxide hydrogel and its use in a supercapacitor. J Mater Chem A1:208–211
Mohammadifar E, Daneshnia F, Kehtari M, Kharat AN, Adeli M (2016) Synthesis of fluorescent ABA triblock copolymer via click reaction. Polym Int 65:559–566
Shey J, Holtman KM, Wong RY, Gregorski KS, Klamczynski AP, Orts WJ, Glenn GM, Imam SH (2006) The azidation of starch. Carbohydr Polym 65:529–534
Kabiri R, Namazi H (2014) Surface grafting of reduced graphene oxide using nanocrystalline cellulose via click reaction. J Nanoparticle Res 16:2474–2487
Ashori A, Bahrami R (2014) Modification of physico-mechanical properties of chitosan-tapioca starch blend films using nano graphene. Polym Plast Technol Eng 53:312–318
Xu LQ, Yee YK, Neoh K-G, Kang E-T, Fu GD (2013) Cyclodextrin-functionalized graphene nanosheets, and their host-guest polymer nanohybrids. Polym J 54:2264–2271
Quemener D, Hellaye ML, Bissett C, Davis TP, Barner-Kowollik C, Stenzel MH (2008) Graft block copolymers of propargyl methacrylate and vinyl acetate via a combination of RAFT/MADIX and click chemistry: reaction analysis. J Polym Sci Part A Polym Chem 46:155–173
Dai Z, Lu Q, Quan Q, Mo R, Zhou C, Hong P, Li C (2017) Novel low temperature (< 37 °C) chitosan hydrogel fabrication under the synergistic effect of graphene oxide. New J Chem 41:671–676
Copello GJ, Mebert AM, Raineri M, Pesenti MP, Diaz LE (2011) Removal of dyes from water using chitosan hydrogel/SiO2 and chitin hydrogel/SiO2 hybrid materials obtained by the sol–gel method. J Hazard Mater 186:932–939
Kaşgöz H (2006) New sorbent hydrogels for removal of acidic dyes and metal ions from aqueous solutions. Polym Bull 56:517–528
Mittal H, Ray SS, Okamoto M (2016) Recent progress on the design and applications of polysaccharide-based graft copolymer hydrogels as adsorbents for wastewater purification. Macromol Mater Eng 301(5):496–522
The authors wish to gratefully acknowledge the support of Lorestan University. The authors declare that they have no conflict of interest.
Electronic supplementary material
Below is the link to the electronic supplementary material.
About this article
Cite this article
Soleimani, K., Dadkhah Tehrani, A., Adeli, M. et al. Convenient method for preparation of a new absorbent based on biofunctionalized graphene oxide hydrogels using nitrene chemistry and click reaction. Iran Polym J 27, 689–699 (2018). https://doi.org/10.1007/s13726-018-0645-2
- Graphene oxide
- Polyethylene glycol
- Click reaction
- Methylene blue
- Nitrene chemistry