β-环糊精和遥爪聚合物C-PDMAEMA的包结行为

doi:10.3866/PKU.WHXB20111019

Abstract

Abstract: A novel photosensitive telechelic polymer C-PDMAEMA was prepared using 2-(dimethylamino) ethyl methacrylate (DAMEMA) as a monomer, azobisisobutyronitrile (AIBN) as inititon, coumarincontaining disulfides (C-S-S-C) as a chain transfer agent in the presence of tributyl phosphine (Bu₃P) and water. Characterization was carried out using ¹H-nuclear magnetic responance (¹H-NMR), gel permeation chromatography (GPC) and Fourier transform infrared (FTIR) spectroscopy. It was found that the coumarin can form a host-guest inclusion complex with β-CD in aqueous solution. The UV-Vis and fluorescence spectra showed that only a 1:1 complex was formed with an inclusion complex K=(1.270±0.062)×10⁴ L· mol^-1. The irradiation experiment showed that this host-guest inclusion might have a very small effect on the photodimerization of coumarin end groups.

Key words: Coumarin, Cyclodextrin, Inclusion complex, Telechelic, Photo-dimerization

JIANG Jin-Qiang, JIANG Tao, ZHANG Cheng-Bang, CHENG Hao, LIU Xiao-Ya, ZHANG Sheng-Wen, CHEN Ming-Qing. Inclusion Behavior of β-Cyclodextrin and Amphiphilic Telechelic Polymer C-PDMAEMA[J]. Acta Phys. -Chim. Sin. 2011, 27(11), 2691-2696. doi: 10.3866/PKU.WHXB20111019

References

(1) Lehn, J. M. Supramolecular Chemistry-Concepts and Perspectives;Wiley-VCH Press: Wchlheim, 1995; pp 1-271.
(2) Awood, J. L.; Daries, J. E. D.; MacNicol, D. M.; V?gtle, F.; Lehn, J. M. Comprehensive Supramolecular Chermistry; Pergamon Press: Oxford, 1996; pp 49-105.
(3) Tong, L. H. Cyclodextrin Chemistry-Fundamentals and Applications; Science Press: Beijing, 2001; pp 92-225.
[童林荟. 环糊精化学——基础与应用. 北京: 科学出版社, 2001: 92-225]
(4) Wenz, G.; Han, B. H.; Müller, A. Chem. Rev. 2006, 106 (3), 782.

(5) Huang, F.; Gibson, H.W. Prog. Polym. Sci. 2005, 30 (10), 982.

(6) Nepogodiev, S. A.; Stoddart, J. F.; Chem. Rev. 1998, 98 (5), 1959.

(7) Rusa, C. C.;Wei, M.; Bullions, T. A.; Rusa, M.; Gomez, M. A.; Porbeni, F. E.;Wang, X.; Shin, I. D.; Balik, C. M.; White, J. L.; Tonelli, A. E. Crys. Grow. Des. 2004, 4 (6), 1431.

(8) Martin, E. M.; Del, V. Pro. Biochem. 2004, 39 (9), 1033.

(9) Tomoki, O.; Akira, H. Sensors 2008, 8, 4961.

(10) Hossain, M. A.; Mihara, H.; Ueno, A. J. Am. Chem. Soc. 2003, 125, 11178.

(11) Hossain, M.A.; Mihara, H.; Ueno, A. Bioorg. Med. Chem. Lett. 2000, 10, 1857.

(12) Connors K. A. Chem. Rev. 1997, 97, 1325.

(13) Wen, Z. L.; Zhang, Z. J. Analyst 1996, 121, 1119.

(14) Lu, J. Z.; Zhang, Z. J. Analyst 1995, 120, 453.

(15) Agjit, S.; Alarie, T. P.; Dinh, T. N. Talanta 1995, 42, 1567.

(16) Paul, S.; Bate, S. Analyst 1994, 119, 181.

(17) Yannis, L.; Loukas. Analyst 1995, 120, 533.

(18) Dang, Z.; Song, L. X.; Pan, S. Z.;Wang, M. Acta Phys. -Chim. Sin. 2009, 25 (6), 1059.
[党政, 宋乐新, 潘淑臻, 王莽. 物理化学学报, 2009, 25 (6), 1059.]
(19) Gao, Y. Y.; Liu, L. H.; Ou, Z. Z.; Li, H.; Yang, G. Q.;Wang, X. S. Acta Phys. -Chim. Sin. 2010, 26 (2), 495.
[高云燕, 刘丽华, 欧植泽, 李好, 杨国强, 王雪松. 物理化学学报, 2010, 26 (2), 495.]
(20) Dang, Z.; Song, L. X. Acta Phys. -Chim. Sin. 2010, 26 (7), 1837.
[党政, 宋乐新. 物理化学学报, 2010, 26 (7), 1837.]
(21) Boisde, P. M.; Meuly, C. Kirk-Othmer Encyel. Chem. Technal. 1993, 7, 647.
(22) Moeekli, P. Dyes and Pigments 1980, 1 (1), 3.

(23) Amendola, V. L.; Mangano, C.; Miller H.; Pallavicini, P.; Perotti, A.; Taglietti, A. Angew. Chem. Int. Edit. 2002, 41 (14), 2553.

(24) Schwander, H. Ullmann, 5th ed.; VCH Verlagsges:Weinheim, 1991; pp l-27.
(25) Raue, R. Ullmann, 5th ed.; VCH Verlagsges:Weinheim, 1991; pp 151-164.
(26) Wang, X. F.; Qu, Y.; Gu, F. Spec. Petrochem. 1999, 49, 52.
[王贤丰, 曲杨, 顾梵. 精细石油化工, 1999, 49, 52.]
(27) Huang, C. H.; Li, F. Y.; Huang, Y. Y. Ultrathin films for Optics and Electronics, 1st ed.; Peking University Press: Beijing, 2001; p 262.
[黄春辉, 李富友, 黄岩谊. 光电功能超薄膜.第一版. 北京: 北京大学出版社, 2001: 262.]
(28) Zhu,W. H.; Tian, H.; Zhu, S. Q. Prog. Chem. 2002, 14 (1), 18.
[朱为宏, 田禾, 朱世琴. 化学进展. 2002, 14 (1), 18.]
(29) Dai, Z. H.;Wu, S. K. Photograp. Sci. Photochem. 2000, 18, 67.
[戴赵华, 吴世康. 感光科学与光化学. 2000, 18, 67.]
(30) Scott, R. T. ; Allan, R. S.; Brian, J. L. ; Timothy, E. L. Chem. Rev. 2004, 104, 3059.

(31) Delzenne, G. A. Europ. Polymer J. Suppl ement 1969, 22, 55.
(32) Schadt, M.; Seiberle, H.; Schuster, A. Nature 1996, 381, 212
(33) Kishore, G. A. K. Macromolecules 1995, 28, 806.
(34) Obi, M.; Morino, S.; Ichimura, K. Chem. Mater. 1999, 11, 656.

(35) Jiang, J. Q.; Qi, B.; Martin, L.; Zhao, Y. Macromolecules 2007, 40, 790.

(36) Jiang, J. Q.; Feng, Y.;Wang, H. M.; Liu, X. Y.; Zhang, S.W.; Chen, M, Q. Acta Phys. -Chim. Sin. 2008, 24 (11), 2089.
[江金强, 冯艳, 王红梅, 刘晓亚, 张胜文, 陈明清, 物理化学学报, 2008, 24 (11), 2089.]
(37) Jackson, P. O.; O’Neill, M.; Duffy,W. L.; Hindmarsh, P.; Kelly, S. M.; Owen, G. J. Chem. Mater. 2001, 13, 694.

(38) Jiang, J. Q.; Shu, Q. Z.; Chen, X.; Yang, Y. Q.; Yi, C. L.; Song, X. Q.; Liu, X. Y.; Chen, M. Q. Langmuir 2010, 26 (17), 14247.

(39) Shu, Q. Z.; Chen, X.; Chen, K. H.; Jiang, J. Q.; Ni, Z. B.; Zhang, H.W.; Liu, X. Y.; Chen, M. Q. Acta Phys. -Chim. Sin. 2010, 26 (10), 2845.
[舒巧珍, 陈欣, 陈开花, 江金强, 倪忠斌, 张红武, 刘晓亚, 陈明清. 物理化学学报, 2010, 26 (10), 2845.]
(40) Jiang, J. Q.; Dai, P.; Zong, Y.W.; Liu, X. Y.; Zhang, S.W.; Chen, M. Q. Acta Phys. -Chim. Sin. 2009, 25 (11), 2285.
[江金强, 代鹏, 宗奕吾, 刘晓亚, 张胜文, 陈明清. 物理化学学报, 2009, 25 (11), 2285.]

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Inclusion Behavior of β-Cyclodextrin and Amphiphilic Telechelic Polymer C-PDMAEMA

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