Covalent functionalization of multi-walled carbon nanotubes with imidazolium-based poly(ionic liquid)s by Diels.Alder “click” reaction

Cuong M.Q. Le; Xuan Thang Cao; Yeon Tae Jeong; Kwon Taek Lim

Journal of Industrial and Engineering Chemistry, Vol.64, 337-343, August, 2018

DOI10.1016/j.jiec.2018.03.034 Export Citation

Covalent functionalization of multi-walled carbon nanotubes with imidazolium-based poly(ionic liquid)s by Diels.Alder “click” reaction

Cuong M.Q. Le, Xuan Thang Cao¹, Yeon Tae Jeong, and Kwon Taek Lim^†

Department of Display Engineering, Pukyong National University, Busan, South Korea
¹Faculty of Chemical Engineering, Industrial University of Ho Chi Minh City, Viet Nam, Vietnam

E-mail:

Imidazolium-based poly(ionic liquid)s grafted on the surface of multiwalled carbon nanotubes (MWNTs) were prepared by Diels.Alder “click” reaction with a high grafting density. Poly(styrene-alt maleic anhydride) (PSM) was functionalized with furfuryl amine and then it was modified with 1-(3- aminopropyl)-3-methylimidazolium bromide to produce poly(ionic liquid)s functionalized with furfuryl groups (PSMF-ILs). PSMF-ILs were directly grafted onto the surface of MWNTs under ultrasonication to form PSMF-IL/MWNT nanocomposites. The material was characterized by FTIR, Raman spectroscopy, XRD, XPS and TEM analyses. The results showed that a very high grafting density was achieved in deep eutectic solvents based on choline chloride:ethylene glycol in a short time.

Keywords:Poly(ionic liquid)s;Multiwalled carbon nanotubes;Diels.Alder reaction

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[Referenced By]

[1] Baughman RH, Zakhidov AA, de Heer WA, Science, 297, 787 (2002)

[2] Li Y, ACS Nano, 11, 1 (2017)

[3] Wang B, Hu C, Dai L, Chem. Commun., 52, 14350 (2016)

[4] Lin CF, Hu L, Cheng CB, Sun K, Guo XK, Shao Q, Li JB, Wang N, Guo ZH, Electrochim. Acta, 260, 65 (2018)

[5] Guan X, Zheng G, Dai K, Liu C, Yan X, Shen C, Guo Z, ACS Appl. Mater. Interfaces, 8, 14150 (2016)

[6] Sun K, Xie PT, Wang ZY, Su TM, Shao Q, Ryu JE, Zhang XH, Guo J, Shankar A, Li JF, Fan RH, Cao DP, Guo ZH, Polymer, 125, 50 (2017)

[7] Li Y, Zhou B, Zheng G, Liu X, Li T, Yan C, Cheng C, Dai K, Liu C, Shen C, Guo Z, J. Mater. Chem. C, 6, 2258 (2018)

[8] Huang J, Mao C, Zhu Y, Jiang W, Yang X, Carbon, 73, 267 (2014)

[9] Yan Y, Miao J, Yang Z, Xiao FX, Yang HB, Liu B, Yang Y, Chem. Soc. Rev., 44, 3295 (2015)

[10] Chen F, Song Z, Nie J, Yu G, Li Z, Lee M, RSC Adv., 6, 81877 (2016)

[11] Habila MA, Yilmaz E, AlOthman ZA, Soylak M, Desalin. Water Treat., 87, 285 (2017)

[12] Alothman ZA, Habila M, Yilmaz E, Soylak M, Microchim. Acta, 177, 397 (2012)

[13] Liu JW, Ye YS, Xue Y, Xie XL, Mai YW, J. Polym. Sci. A: Polym. Chem., 55(4), 622 (2017)

[14] Tasis D, Tagmatarchis N, Bianco A, Prato M, Chem. Rev., 106(3), 1105 (2006)

[15] Karousis N, Tagmatarchis N, Tasis D, Chem. Rev., 110(9), 5366 (2010)

[16] Dinesh B, Bianco A, Menard-Moyon C, Nanoscale, 8, 18596 (2016)

[17] Hu Z, Shao Q, Xu X, Zhang D, Huang Y, Compos. Sci. Technol., 142, 294 (2017)

[18] Tasdelen MA, Polym. Chem., 2, 2133 (2011)

[19] Zydziak N, Yameen B, Barner-Kowollik C, Polym. Chem., 4, 4072 (2013)

[20] Sun JT, Zhao LY, Hong CY, Pan CY, Chem. Commun., 47, 10704 (2011)

[21] Shaplov AS, Ponkratov DO, Vygodskii YS, Polym. Sci. Ser. B, 58, 73 (2016)

[22] Qian W, Texter J, Yan F, Chem. Soc. Rev., 46, 1124 (2017)

[23] Bui-Thi-Tuyet V, Trippe-Allard G, Ghilane J, Randriamahazaka H, ACS Appl. Mater. Interfaces, 8, 28316 (2016)

[24] Zhang Y, Wang B, Elageed EHM, Qin L, Ni B, Liu X, Gao G, ACS Macro Lett., 5, 435 (2016)

[25] Qiao YX, Ma WB, Theyssen N, Chen C, Hou ZS, Chem. Rev., 117(10), 6881 (2017)

[26] Horne WJ, Andrews MA, Terrill KL, Hayward SS, Marshall J, Belmore KA, Shannon MS, Bara JE, ACS Appl. Mater. Interfaces, 7, 8979 (2015)

[27] Hernandez G, Isik M, Mantione D, Pendashteh A, Navalpotro P, Shanmukaraj D, Marcilla R, Mecerreyes D, J. Mater. Chem. A, 5, 16231 (2017)

[28] Tunckol M, Hernandez EZ, Sarasua JR, Durand J, Serp P, Eur. Polym. J., 49, 3770 (2013)

[29] Zhang H, Hu Z, Li M, Hu L, Jiao S, J. Mater. Chem. A, 2, 17024 (2014)

[30] Li T, Cui Z, Yuan W, Li CM, RSC Adv., 6, 12792 (2016)

[31] Biswas Y, Maji T, Dule M, Mandal TK, Polym. Chem., 7, 867 (2016)

[32] Zhao L, Yang J, Ye H, Zhao F, Zeng B, RSC Adv., 7, 4704 (2017)

[33] Chen XM, Ren TQ, Ma M, Wang ZG, Zhan GQ, Li CY, Electrochim. Acta, 111, 49 (2013)

[34] Li XY, Liu YX, Zheng LC, Dong MJ, Xue ZH, Lu XQ, Liu XH, Electrochim. Acta, 113, 170 (2013)

[35] Kim T, Tung TT, Lee T, Kim J, Suh KS, J. Chem. Asian, 5, 256 (2010)

[36] Tang R, Shi Y, Hou Z, Wei L, Sensors, 17, 882 (2017)

[37] Gendron D, Ansaldo A, Bubak G, Ceseracciu L, Vamvounis G, Ricci D, Compos. Sci. Technol., 117, 364 (2015)

[38] Li Q, Liu L, Liang S, Dong Q, Jin B, Bai R, RSC Adv., 3, 13477 (2013)

[39] Wu M, Wang L, Zeng B, Zhao F, J. Chromatogr. A, 1444, 42 (2016)

[40] Li Y, Li G, Wang X, Zhu Z, Ma H, Zhang T, Jin J, Chem. Commun., 48, 8222 (2012)

[41] Le CMQ, Cao XT, Lim KT, Ultrason. Sonochem., 39, 321 (2017)

[42] Namboodiri VV, Varma RS, Org. Lett., 4, 3161 (2002)

[43] Pramanik NB, Singha NK, RSC Adv., 5, 94321 (2015)

[44] Zydziak N, Hubner C, Bruns M, Barner-Kowollik C, Macromolecules, 44(9), 3374 (2011)

[45] Yameen B, Rodriguez-Emmenegger C, Ahmed I, Preuss CM, Durr CJ, Zydziak N, Trouillet V, Fruk L, Barner-Kowollik C, Chem. Commun., 49, 6734 (2013)

[46] Zydziak N, Hubner C, Bruns M, Vogt AP, Barner-Kowollik C, Polym. Chem., 4, 1525 (2013)

[47] Otto S, Engberts JB, Pure Appl. Chem., 72, 1365 (2000)

[48] Reinhardt D, Ilgen F, Kralisch D, Konig B, Kreisel G, Green Chem., 10, 1170 (2008)

[49] Imperato G, Eibler E, Niedermaier J, Konig B, Chem. Commun. (Camb.), 1170 (2005).

[50] Ilgen F, Konig B, Green Chem., 11, 848 (2009)

[51] AlOmar MK, Alsaadi MA, Jassam TM, Akib S, Hashim MA, J. Colloid Interface Sci., 497, 413 (2017)

[52] Abo-Hamad A, Hayyan M, AlSaadi MA, Mirghani MES, Hashim MA, J. Chem. Eng., 311, 326 (2017)

[53] Mota-Morales JD, Gutierrez MC, Ferrer ML, Jimenez R, Santiago P, Sanchez IC, Terrones M, Del Monte F, Luna-Barcenas G, J. Mater. Chem. A, 1, 3970 (2013)

[54] Mondal D, Bhatt J, Sharma M, Chatterjee S, Prasad K, Chem. Commun., 50, 3989 (2014)

[55] Abo-Hamad A, Hayyan M, AlSaadi MA, Hashim MA, J. Chem. Eng., 273, 551 (2015)

[56] Durand E, Lecomte J, Villeneuve P, Eur. J. Lipid Sci. Technol., 115, 379 (2013)

[57] Handy S, Deep Eutectic Solvents in Organic Synthesis (2015).