One-Pot Synthesis of Bicyclic Polystyrene by Combination of ATRP and Click Chemistry

Hyerin Choi; Taeheon Lee; Jonghwa Jeong; Jihwa Ye; Heung Bae Jeon; Hyun-jong Paik

Macromolecular Research, Vol.24, No.10, 856-861, October, 2016

DOI10.1007/s13233-016-4119-0 Export Citation

One-Pot Synthesis of Bicyclic Polystyrene by Combination of ATRP and Click Chemistry

Hyerin Choi, Taeheon Lee, Jonghwa Jeong, Jihwa Ye, Heung Bae Jeon¹, and Hyun-jong Paik^†

Department of Polymer Science and Engineering, Pusan National University, Busan, Korea
¹Department of Chemistry, Kwangwoon University, Seoul, Korea

E-mail:

A series of bicyclic polystyrenes of different molecular weights was synthesized in one-pot by atom transfer radical polymerization followed by click chemistry. The bicyclic polystyrenes were formed simultaneously with branched polystyrene impurities due to side reactions during click coupling. The pure bicyclic polystyrenes were obtained by selective precipitation. The purity of bicyclic polystyrenes before purification was determined by Gaussian multiple peak fitting from SEC trace. The bicyclic polymers were characterized by SEC, 1H NMR, and FTIR spectroscopy.

Keywords:atom transfer radical polymerization;click chemistry;one-pot synthesis;macrocyclization;bicyclic polymer

[References]

Ishizu K, Uchida S, Prog. Polym. Sci, 24, 1439 (1999)
Yang LP, Zhou HX, Shi GY, Wang Y, Pan CY, J. Polym. Sci. A: Polym. Chem., 46(19), 6641 (2008)
Pyun J, Kowalewski T, Matyjaszewski K, Macromol. Rapid Commun., 24(18), 1043 (2003)
Inoue K, Prog. Polym. Sci, 25, 453 (2000)
Yamamoto T, Tezuka Y, J. Polym. Sci. A: Polym. Chem., 2, 1930 (2011)
Kricheldorf HR, J. Polym. Sci. A: Polym. Chem., 48(2), 251 (2010)
Nasongkla N, Chen B, Macaraeg N, Fox ME, Frechet JMJ, Szoka FC, J. Am. Chem. Soc., 131(11), 3842 (2009)
Ge ZS, Wang D, Zhou YM, Liu HW, Liu SY, Macromolecules, 42(8), 2903 (2009)
Ko YS, Yamamoto T, Tezuka Y, Macromol. Rapid Commun., 35(4), 412 (2014)
Shi GY, Pan CY, J. Polym. Sci. A: Polym. Chem., 47(10), 2620 (2009)
Jeong J, Kim H, Lee S, Choi H, Jeon HB, Paik HJ, Polymer, 72, 447 (2015)
Jeong J, Kim K, Lee R, Lee S, Kim H, Jung H, Kadir MA, Jang Y, Jeon HB, Matyjaszewski K, Chang T, Paik HJ, Macromolecules, 47(12), 3791 (2014)
Lord SJ, Sheiko SS, LaRue I, Lee HI, Matyjaszewski K, Macromolecules, 37(11), 4235 (2004)
Doi Y, Ohta Y, Nakamura M, Takano A, Takahashi Y, Matsushita Y, Macromolecules, 46(3), 1075 (2013)
Schappacher M, Deffieux A, Macromolecules, 28(8), 2629 (1995)
Lee T, Oh J, Jeong J, Jung H, Huh J, Chang T, Paik HJ, Macromolecules, 49(10), 3672 (2016)
Fan XS, Huang B, Wang GW, Huang JL, Macromolecules, 45(9), 3779 (2012)
Shi GY, Sun JT, Pan CY, Macromol. Chem. Phys., 212, 1305 (2011)
Wan XJ, Liu T, Liu SY, Biomacromolecules, 12(4), 1146 (2011)
Laurent BA, Grayson SM, Chem. Soc. Rev., 38, 2202 (2009)
Jia ZF, Monteiro MJ, J. Polym. Sci. A: Polym. Chem., 50(11), 2085 (2012)
Carnicom EM, Tillman ES, React. Funct. Polym., 80, 9 (2014)
Zhu X, Zhou NC, Zhu J, Zhang ZB, Zhang W, Cheng ZP, Tu YF, Zhu XL, Macromol. Rapid Commun., 34(12), 1014 (2013)
Tsarevsky NV, Sumerlin BS, Matyjaszewski K, Macromolecules, 38(9), 3558 (2005)
Lundberg P, Hawker CJ, Hult A, Malkoch M, Macromol. Rapid Commun., 29(12-13), 998 (2008)

[1] Ishizu K, Uchida S, Prog. Polym. Sci, 24, 1439 (1999)

[2] Yang LP, Zhou HX, Shi GY, Wang Y, Pan CY, J. Polym. Sci. A: Polym. Chem., 46(19), 6641 (2008)

[3] Pyun J, Kowalewski T, Matyjaszewski K, Macromol. Rapid Commun., 24(18), 1043 (2003)

[4] Inoue K, Prog. Polym. Sci, 25, 453 (2000)

[5] Yamamoto T, Tezuka Y, J. Polym. Sci. A: Polym. Chem., 2, 1930 (2011)

[6] Kricheldorf HR, J. Polym. Sci. A: Polym. Chem., 48(2), 251 (2010)

[7] Nasongkla N, Chen B, Macaraeg N, Fox ME, Frechet JMJ, Szoka FC, J. Am. Chem. Soc., 131(11), 3842 (2009)

[8] Ge ZS, Wang D, Zhou YM, Liu HW, Liu SY, Macromolecules, 42(8), 2903 (2009)

[9] Ko YS, Yamamoto T, Tezuka Y, Macromol. Rapid Commun., 35(4), 412 (2014)

[10] Shi GY, Pan CY, J. Polym. Sci. A: Polym. Chem., 47(10), 2620 (2009)

[11] Jeong J, Kim H, Lee S, Choi H, Jeon HB, Paik HJ, Polymer, 72, 447 (2015)

[12] Jeong J, Kim K, Lee R, Lee S, Kim H, Jung H, Kadir MA, Jang Y, Jeon HB, Matyjaszewski K, Chang T, Paik HJ, Macromolecules, 47(12), 3791 (2014)

[13] Lord SJ, Sheiko SS, LaRue I, Lee HI, Matyjaszewski K, Macromolecules, 37(11), 4235 (2004)

[14] Doi Y, Ohta Y, Nakamura M, Takano A, Takahashi Y, Matsushita Y, Macromolecules, 46(3), 1075 (2013)

[15] Schappacher M, Deffieux A, Macromolecules, 28(8), 2629 (1995)

[16] Lee T, Oh J, Jeong J, Jung H, Huh J, Chang T, Paik HJ, Macromolecules, 49(10), 3672 (2016)

[17] Fan XS, Huang B, Wang GW, Huang JL, Macromolecules, 45(9), 3779 (2012)

[18] Shi GY, Sun JT, Pan CY, Macromol. Chem. Phys., 212, 1305 (2011)

[19] Wan XJ, Liu T, Liu SY, Biomacromolecules, 12(4), 1146 (2011)

[20] Laurent BA, Grayson SM, Chem. Soc. Rev., 38, 2202 (2009)

[21] Jia ZF, Monteiro MJ, J. Polym. Sci. A: Polym. Chem., 50(11), 2085 (2012)

[22] Carnicom EM, Tillman ES, React. Funct. Polym., 80, 9 (2014)

[23] Zhu X, Zhou NC, Zhu J, Zhang ZB, Zhang W, Cheng ZP, Tu YF, Zhu XL, Macromol. Rapid Commun., 34(12), 1014 (2013)

[24] Tsarevsky NV, Sumerlin BS, Matyjaszewski K, Macromolecules, 38(9), 3558 (2005)

[25] Lundberg P, Hawker CJ, Hult A, Malkoch M, Macromol. Rapid Commun., 29(12-13), 998 (2008)