RAFT试剂N-咔唑二硫代甲酸1,4-对二甲基苯双酯的合成及应用

高等学校化学学报 ›› 2009, Vol. 30 ›› Issue (8): 1668.

RAFT试剂N-咔唑二硫代甲酸1,4-对二甲基苯双酯的合成及应用

张建华1, 郭睿威2, 李彬2, 董岸杰2

1. 天津大学材料学院,
2. 化工学院, 天津 300072

收稿日期:2008-12-17 出版日期:2009-08-10 发布日期:2009-08-10
通讯作者: 郭睿威, 男, 博士, 副教授, 主要从事活性聚合及功能高分子研究. E-mail: rwguo@263.net

Synthesis and Application of RAFT Agent p-Xylylene Di(N-carbazylcarbodithioate)

ZHANG Jian-Hua¹, GUO Rui-Wei^2*, LI Bin², DONG An-Jie²

1. School of Material Science and Engineering,
2. School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China

Received:2008-12-17 Online:2009-08-10 Published:2009-08-10
Contact: GUO Rui-Wei. E-mail: rwguo@263.net

摘要/Abstract

摘要：

以咔唑和对二氯甲基苯为原料, 合成了以咔唑为Z基团的双功能团RAFT聚合链转移试剂N-咔唑二硫代甲酸1,4-对二甲基苯双酯(PXCBD). 以PXCBD为链转移试剂, 以苯乙烯、丙烯酸甲酯及N,N-二丁基丙烯酰胺为单体, 考察了PXCBD在RAFT聚合中合成多嵌段共聚物上的应用, 并研究了PXCBD及由其合成的聚合物的荧光特性. 研究结果表明, PXCBD是一种性能优异的双功能团RAFT聚合链转移试剂, 可用于合成特殊结构并且带有荧光标识的功能高分子材料.

关键词: N-咔唑二硫代甲酸1,4-对二甲基苯双酯; 可逆加成-断裂链转移聚合(RAFT)试剂; 嵌段共聚物; 荧光标识

Abstract:

A double-functional reversible addition fragmentation chain transfer radical polymerization(RAFT) agent p-xylylene di(N-carbazylcarbodithioate)(PXCBD) was synthesized with carbazole and 1,4-bis(chloro-methyl)benzene as main material. With PXCBD as a chain transfer agent, the well-defined triblock and pen-tablock polymers were controllably synthesized by RAFT polymerization of styrene, methyl acrylate and N,N-dibutylacrylamide. The fluorescence characteristic of PXCBD and polymers prepared by PXCBD were studied. The results show that PXCBD as RAFT agent possesses good control ability and can be used to synthesize fluorescence-labelled polymers with well-defined structure.

Key words: Para-Xylylene di(N-carbazylcarbodithioate); Reversible addition fragmentation chain transfer radical polymerization(RAFT) agent; Block copolymer; Fluorescence-labelled

TrendMD:

张建华, 郭睿威, 李彬, 董岸杰. RAFT试剂N-咔唑二硫代甲酸1,4-对二甲基苯双酯的合成及应用. 高等学校化学学报, 2009, 30(8): 1668.

ZHANG Jian-Hua, GUO Rui-Wei*, LI Bin, DONG An-Jie. Synthesis and Application of RAFT Agent p-Xylylene Di(N-carbazylcarbodithioate). Chem. J. Chinese Universities, 2009, 30(8): 1668.

参考文献

[1]Chiefari J., Chong Y. K., Ercole F., et al.. Macromolecules[J], 1998, 31(16): 5559—5562
[2]Moad G., Chiefari J., Chong Y. K., et al.. Polym. Inter.[J], 2000, 49: 993—1001
[3]LIU Chun-Hua(刘春华), PAN Cai-Yuan(潘才元). Chem. J. Chinese Universities(高等学校化学学报)[J], 2008, 29(2): 404—408
[4]PAN Jing-Yuan(潘景云), HE Jun-Po(何军坡), JIANG Hong-Jin(姜洪进), et al.. Chem. J. Chinese Universities(高等学校化学学报)[J], 2004, 25S(9): 1759—1764
[5]SHAO Ya-Jun(邵亚军), NI Pei-Hong(倪沛红), JI Xiao-Li(纪晓丽), et al.. Chem. J. Chinese Universities(高等学校化学学报)[J], 2004, 25(11): 2176—2178
[6]Chen Y., Ying L., Yu W. H.. Macromolecules[J], 2003, 36(25): 9451—9457
[7]Roshan T. A. M., Rizzardo E., John C. R., et al.. Macromolecules[J], 2000, 33(2): 243—245
[8]Chong Y. K., Le T. P. T., Moad G., et al.. Macromolecules[J], 1999, 32(6): 2071—2074
[9]Moad G., Roshan T. A. M., Rizzardo E., et al.. Macromol. Symp.[J], 2003, 192: 1—12
[10]Murat M., Andr L., Skrabauia K., et al.. Macromolecules[J], 2005, 38(9): 3601—3614
[11]Zhang J. H., Dong A. J., Cao T. Y., et al.. Eur. Polym. J.[J], 2008, 44: 1071—1080
[12]GUO Rui-Wei(郭睿威), ZHANG Jian-Hua(张建华), ZHAO Zong-Feng(赵宗峰), et al.. J. Tianjin University(天津大学学报)[J], 2007, 40(8): 906—910
[13]GUO Rui-Wei(郭睿威), QI Gui-Cun(戚桂村), FANG Dao-Bin(方道斌). Synthesis and Application of RAFT Agent Carbazolyl Carbodithioate(咔唑二硫代甲酸酯及AFT试剂的制备方法与应用), CN 200410072592[P], 2005
[14]Hua D. B., Zhang J. X., Bai R. K., et al.. Macromol. Chem. Phys.[J], 2004, 205: 1125—1130
[15]Zhou D., Zhu X.L., Zhu J., et al.. J. Polym. Sci. Part A: Polym. Chem.[J], 2005, 43: 4849—4856
[16]ZHANG Jian-Hua(张建华), Synthesis of Carbazyl RAFT Reagents and Application in RAFT Polymerization(新型咔唑基RAFT试剂的新合成工艺与聚合研究)[D], Tianjin: Tianjin University, School of Chemical Engineering and Techadoegy, 2007
[17]Wang S. M., Cheng Z. P., Zhu J., et al.. J. Polym. Sci. Part A: Polym. Chem.[J], 2007, 45: 5318—5328
[18]Charles W. S., Anthony J. C., Charles L. M.. Biomacromolecules[J], 2006, 7: 1389—1392
[19]Martínez-Mǎńnez R., Sancenón F.. Chem. Rev.[J], 2003, 103(11): 4419—4476
[20]ZHANG Hao(张皓), YANG Bai(杨柏). Chem. J. Chinese Universities(高等学校化学学报)[J], 2008, 29(2): 217—229