Thiol-Ene photopolymerization of well-defined hybrid graft polymers from a ladder-like polysilsesquioxane

Albert Sung Soo Lee; Seung-Sock Choi; Kyung-Youl Baek; Seung Sang Hwang

Macromolecular Research, Vol.23, No.1, 60-66, January, 2015

DOI10.1007/s13233-015-3004-6 Export Citation

Thiol-Ene photopolymerization of well-defined hybrid graft polymers from a ladder-like polysilsesquioxane

Albert Sung Soo Lee^{1, 2}, Seung-Sock Choi^{1, 3}, Kyung-Youl Baek^{1, 2}, and Seung Sang Hwang^{1, 2, †}

¹Center for Materials Architecturing, Korea Institute of Science and Technology, Seong Buk Gu, Hawolgok Dong 39-1, Seoul, 136-791, Korea
²University of Science and Technology, Nanomaterials Science and Engineering, Yuseong Gu, Daejeon, 305-333, Korea
³, Korea

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A ladder-like structured poly(mercaptopropyl)silsesquioxane (LPMPSQ) was synthesized in one-bath, under mildly basic conditions at room temperature. Obtained LPMPSQ was utilized as a macroinitiator for thiol-ene graft photopolymerization of various vinyl monomers to give hard, soft, hydrophobic, and hydrophilic graft copolymers with low PDI (<1.4). Synthesized hybrid graft copolymers were characterized by 1H NMR, 29Si NMR, FTIR, GPC, TGA, and DSC. Thermal studies with these hybrid graft copolymers revealed that the ladder-structure substantially increased the thermal stabilities in the form of increased glass transition temperatures and higher degradation temperatures over their organic analogues.

Keywords:polysilsesquioxane;ladder-like structure;photopolymerzation;hybrids;thiol-ene

[References]

Baney RH, Itoh M, Sakakibara A, Suzuki T, Chem. Rev., 95(5), 1409 (1995)
Loy DA, Shea KJ, Chem. Rev., 95(5), 1431 (1995)
Volksen W, Miller RD, Dubois G, Chem. Rev., 110(1), 56 (2010)
Sulaiman S, Bhaskar A, Zhang J, Guda R, Goodson T, Laine R, Chem. Mater., 20, 5563 (2008)
Gerritsen G, Duchateau R, van Santen RA, Yap GPA, Organometallics, 22, 100 (2003)
Kim H, Wallraff G, Kreller CR, Angelos S, Lee VY, Volksen W, Miller RD, Nano Lett., 4, 1169 (2004)
Ni C, Wu G, Zhu C, Yao B, J. Phys. Chem. C, 114, 13471 (2010)
Nguyen CV, Carter KR, Hawker CJ, Hendrick JL, Jaffe RL, Miller RD, Remenar JF, Rhee H, Rice PM, Toney MF, Trollsas M, Yoon DY, Chem Mater., 11, 3080 (1999)
Cordes DB, Lickiss PD, Rataboul F, Chem. Rev., 11, 2081 (2010)
Brown F, Vogt LH, Katchman A, Eustance JW, Kiser KM, Krantz KW, J. Am. Chem. Soc., 82, 6194 (1960)
Andrianov KA, Pavlova SA, Tverdokhlebova II, Yemel’yanov VN, Larina TA, Rabkina AY, Polym. Sci. U.S.S.R., 14, 2628 (1972)
Lee ASS, Choi SS, Lee HS, Jeon HY, Baek KY, Hwang SS, J. Polym. Sci. A: Polym. Chem., 50(21), 4563 (2012)
Choi SS, Lee AS, Lee HS, Jeon HY, Baek KY, Choi DH, Hwang SS, J. Polym. Sci. A: Polym. Chem., 49(23), 5012 (2011)
Unno M, Matsumoto T, Matsumoto H, J. Organomet. Chem., 692, 307 (2007)
Zhang ZX, Hao J, Xie P, Zhang X, Han CC, Zhang R, Chem. Mater., 20, 1322 (2008)
Kotal A, Si S. Paira TK, Mandal TK, J. Polym. Sci. Part A: Polym. Chem., 46, 1111 (2007)
Ge ZS, Wang D, Zhou YM, Liu HW, Liu SY, Macromolecules, 42(8), 2903 (2009)
Ro HW, Kim KJ, Theato P, Gidley DW, Yoon DY, Macromolecules, 38(3), 1031 (2005)
Choi SS, Lee AS, Lee HS, Choi DH, Hwang SS, Baek KY, Mol. Cryst. Liq. Cryst., 539, 174 (2011)
Hoyle CE, Brown CN, Angew. Chem. Int. Ed., 49, 1540 (2010)
Hoyle CE, Lowe AB, Brown CN, Chem. Soc. Rev., 39, 1355 (2010)
Yhaya F, Sutinah A, Gregory AM, Liang MT, Stenzel MH, J. Polym. Sci. A: Polym. Chem., 50(19), 4085 (2012)
Lowe AB, Polym. Chem., 1, 17 (2010)
Tucker-Schwartz AK, Farrell RA, Garrell RL, J. Am. Chem. Soc., 133(29), 11026 (2011)
Yamamot S, Shimada R, Kimura A, Sugizaki T, Moriya O, Polym. J., 36, 761 (2004)
Moriya O, Kuga M, Yamamoto S, Kashio M, Kamejima A, Sugizaki T, Polymer, 47(6), 1837 (2006)
Cramer NB, Bowman CN, J. Polym. Sci. Part A: Polym. Chem.,, 29, 3311 (2001)
Cramer NB, Reddy SK, Cole M, Hoyle C, Bowman CN, J. Polym. Sci. A: Polym. Chem., 42(22), 5817 (2004)
Mark JE, Polymer Data Handbook, 2nd ed., Oxford University Press, Inc., New York, p 483. (1999)
Cao C, Lin Y, J. Chem. Inf. Comput. Sci., 43, 643 (2003)

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[2] Loy DA, Shea KJ, Chem. Rev., 95(5), 1431 (1995)

[3] Volksen W, Miller RD, Dubois G, Chem. Rev., 110(1), 56 (2010)

[4] Sulaiman S, Bhaskar A, Zhang J, Guda R, Goodson T, Laine R, Chem. Mater., 20, 5563 (2008)

[5] Gerritsen G, Duchateau R, van Santen RA, Yap GPA, Organometallics, 22, 100 (2003)

[6] Kim H, Wallraff G, Kreller CR, Angelos S, Lee VY, Volksen W, Miller RD, Nano Lett., 4, 1169 (2004)

[7] Ni C, Wu G, Zhu C, Yao B, J. Phys. Chem. C, 114, 13471 (2010)

[8] Nguyen CV, Carter KR, Hawker CJ, Hendrick JL, Jaffe RL, Miller RD, Remenar JF, Rhee H, Rice PM, Toney MF, Trollsas M, Yoon DY, Chem Mater., 11, 3080 (1999)

[9] Cordes DB, Lickiss PD, Rataboul F, Chem. Rev., 11, 2081 (2010)

[10] Brown F, Vogt LH, Katchman A, Eustance JW, Kiser KM, Krantz KW, J. Am. Chem. Soc., 82, 6194 (1960)

[11] Andrianov KA, Pavlova SA, Tverdokhlebova II, Yemel’yanov VN, Larina TA, Rabkina AY, Polym. Sci. U.S.S.R., 14, 2628 (1972)

[12] Lee ASS, Choi SS, Lee HS, Jeon HY, Baek KY, Hwang SS, J. Polym. Sci. A: Polym. Chem., 50(21), 4563 (2012)

[13] Choi SS, Lee AS, Lee HS, Jeon HY, Baek KY, Choi DH, Hwang SS, J. Polym. Sci. A: Polym. Chem., 49(23), 5012 (2011)

[14] Unno M, Matsumoto T, Matsumoto H, J. Organomet. Chem., 692, 307 (2007)

[15] Zhang ZX, Hao J, Xie P, Zhang X, Han CC, Zhang R, Chem. Mater., 20, 1322 (2008)

[16] Kotal A, Si S. Paira TK, Mandal TK, J. Polym. Sci. Part A: Polym. Chem., 46, 1111 (2007)

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

[18] Ro HW, Kim KJ, Theato P, Gidley DW, Yoon DY, Macromolecules, 38(3), 1031 (2005)

[19] Choi SS, Lee AS, Lee HS, Choi DH, Hwang SS, Baek KY, Mol. Cryst. Liq. Cryst., 539, 174 (2011)

[20] Hoyle CE, Brown CN, Angew. Chem. Int. Ed., 49, 1540 (2010)

[21] Hoyle CE, Lowe AB, Brown CN, Chem. Soc. Rev., 39, 1355 (2010)

[22] Yhaya F, Sutinah A, Gregory AM, Liang MT, Stenzel MH, J. Polym. Sci. A: Polym. Chem., 50(19), 4085 (2012)

[23] Lowe AB, Polym. Chem., 1, 17 (2010)

[24] Tucker-Schwartz AK, Farrell RA, Garrell RL, J. Am. Chem. Soc., 133(29), 11026 (2011)

[25] Yamamot S, Shimada R, Kimura A, Sugizaki T, Moriya O, Polym. J., 36, 761 (2004)

[26] Moriya O, Kuga M, Yamamoto S, Kashio M, Kamejima A, Sugizaki T, Polymer, 47(6), 1837 (2006)

[27] Cramer NB, Bowman CN, J. Polym. Sci. Part A: Polym. Chem.,, 29, 3311 (2001)

[28] Cramer NB, Reddy SK, Cole M, Hoyle C, Bowman CN, J. Polym. Sci. A: Polym. Chem., 42(22), 5817 (2004)

[29] Mark JE, Polymer Data Handbook, 2nd ed., Oxford University Press, Inc., New York, p 483. (1999)

[30] Cao C, Lin Y, J. Chem. Inf. Comput. Sci., 43, 643 (2003)