Facile synthesis of block copolymers from a cinnamate derivative by combination of AGET ATRP and click chemistry

Chuanjie Cheng; Xiongxiong Bai; Xu Zhang; Ming Chen; Qinghua Huang; Zhongyu Hu; Yuanming Tu

Macromolecular Research, Vol.22, No.12, 1306-1311, December, 2014

DOI10.1007/s13233-014-2180-0 Export Citation

Facile synthesis of block copolymers from a cinnamate derivative by combination of AGET ATRP and click chemistry

Chuanjie Cheng^†, Xiongxiong Bai, Xu Zhang, Ming Chen, Qinghua Huang, Zhongyu Hu, and Yuanming Tu

Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Fenglin Street, Nanchang, Jiangxi, 330013, P. R. China

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An azido- and bromo-containing compound derived from naturally occurring ethyl cinnamate was used successfully to prepare block copolymers by a combination of ‘activator generated by electron transfer atom transfer radical polymerization’ (AGET ATRP) and Huisgen “click” reactions in emulsion. First, azido-end poly(methyl methacrylate) and alkyne-end polystyrene were prepared under AGET ATRP conditions, then, poly(methyl methacrylate) block polystyrene (PMMA-b-PS) diblock copolymer was formed by Huisgen 1,3-dipolar cycloaddition. Finally, polystyrene block poly(methyl methacrylate) block polystyrene (PS-b-PMMA-b-PS) triblock copolymer was synthesized via simultaneous AGET ATRP and click reactions, catalyzed by the same copper-based catalyst. The polymers were characterized by 1H nuclear magnetic resonance (NMR) spectroscopy and gel permeation chromatography (GPC), which confirmed the successful synthesis of the corresponding polymers.

Keywords:block copolymer;AGET ATRP;“click” reaction;simultaneous

[References]

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[Referenced By]

[1] Yamamotoam T, Tezuka Y, Polym. Chem., 2, 1930 (2011)

[2] Hu J, He JL, Zhang MZ, Ni PH, Acta Polymerica Sinica, 3, 300 (2013)

[3] Bai Y, Fan XD, Mu CG, Yang Z, Wang D, Zhang HT, Prog. Chem., 25, 363 (2013)

[4] Sai H, Tan KW, Hur K, Asenath-Smith E, Hovden R, Jiang Y, Riccio M, Muller DA, Elser V, Estroff LA, Gruner SM, Wiesner U, Science, 341(6145), 530 (2013)

[5] Onses MS, Song C, Williamson L, Sutanto E, Ferreira PM, Alleyne AG, Nealey PF, Ahn H, Rogers JA, Nat. Nanotechnol., 8(9), 667 (2013)

[6] Kumar S, Lee JS, Murthy CN, Macromol. Res., 19(10), 1022 (2011)

[7] Cheng C, Fu Q, Liu Z, Shen L, Qiao Y, Fu C, Macromol. Res., 19(10), 1048 (2011)

[8] Kim BS, Lee HK, Jeong S, Lee JO, Paik H, Macromol. Res., 19(12), 1257 (2011)

[9] Song IY, Kwon YS, Lim J, Park T, ACS Nano, 8, 6893 (2014)

[10] Im MJ, Moon BJ, Lee GY, Son SY, Park T, J. Polym. Sci. A: Polym. Chem., 52(8), 1068 (2014)

[11] Schacher FH, Rupar PA, Manners I, Angew. Chem. Int. Ed., 51, 7898 (2012)

[12] Mai YY, Eisenberg A, Chem. Soc. Rev., 41, 5969 (2012)

[13] Luo M, Epps TH, Macromolecules, 46(19), 7567 (2013)

[14] Tavakkoli KGA, Gotrik KW, Hannon AF, Alexander-Katz A, Ross CA, Berggren KK, Science, 336(6086), 1294 (2012)

[15] Hadjichristidis N, Pitsikalis M, Iatrou H, Adv. Polym. Sci., 189, 1 (2005)

[16] Gu YY, Lodge TP, Macromolecules, 44(7), 1732 (2011)

[17] de Freitas AGO, Trindade SG, Muraro PIR, Schmidt V, Satti AJ, Villar MA, Ciolino AE, Giacomelli C, Macromol. Chem. Phys., 214, 2336 (2013)

[18] Khan MY, Chen X, Noh SK, Macromol. Res., 21(4), 442 (2013)

[19] Quemener D, Davis TP, Barner-Kowollik C, Stenzel MH, Chem. Commun., 5051 (2006)

[20] Jiang XB, Hu L, Chen YM, Polym. Int., 62, 1777 (2013)

[21] Yilmaz G, Iskin B, Yagci Y, Macromol. Chem. Phys., 215, 662 (2014)

[22] Tasdelen MA, Yagci Y, Angew. Chem. Int. Ed., 52, 5930 (2013)

[23] Uygun M, Tasdelen MA, Yagci Y, Macromol. Chem. Phys., 211, 103 (2010)

[24] Zhang Q, Wang XY, Cheng CJ, Zhu R, Liu N, Hu YF, Org. Biomol. Chem., 10, 2847 (2012)

[25] Chen JC, Liu MZ, Gong HH, Cui GJ, Lu SY, Gao CM, Huang F, Chen TT, Zhang XY, Liu Z, Polym. Chem., 4, 1815 (2013)

[26] Huang C, Neoh KG, Kang ET, Langmuir, 28(1), 563 (2012)

[27] Liu HH, Li SX, Zhang MJ, Shao W, Zhao YL, J. Polym. Sci. A: Polym. Chem., 50(22), 4705 (2012)

[28] Cheng CJ, Bai XX, Liu SJ, Huang QH, Tu YM, Wu HW, Wang XJ, J. Polym. Res., 20, 197 (2013)

[29] Lligadas G, Macromol. Chem. Phys., 214, 415 (2013)

[30] Todros S, Natali AN, Pace G, Di Noto V, Macromol. Chem. Phys., 214, 2061 (2013)

[31] Saengthong S, Piroonpan T, Tangthong T, Pasanphan W, Macromol. Res., 22(7), 717 (2014)

[32] Ayutthaya WDN, Poompradub S, Macromol. Res., 22(7), 686 (2014)

[33] Huang QH, Chen M, Bai XX, Gu LL, Tu YM, Cheng CJ, Chemical Research and Application, 26, 277 (2014)

[34] Saikia I, Phukan P, C. R. Chim., 15, 688 (2012)

[35] Pan JL, Miao J, Zhang LF, Si ZY, Zhang CW, Cheng ZP, Zhu XL, Polym. Chem., 4, 5664 (2013)

[36] Zhang HY, Zhang YM, Liu WW, Wang HP, J. Appl. Polym. Sci., 110(1), 244 (2008)

[37] Xu LQ, Yao F, Fu GD, Kang ET, Biomacromolecules, 11(7), 1810 (2010)

[38] Zhang YF, Li CH, Liu SY, J. Polym. Sci. A: Polym. Chem., 47(12), 3066 (2009)

[39] Yao F, Xu LQ, Fu GD, Lin BP, Macromolecules, 43(23), 9761 (2010)

[40] Li W, Xu YH, Zhou Y, Ma WH, Wang SX, Dai YN, Nanoscale Res. Lett., 7, 485 (2012)