Design and Synthesis of α-Cyclodextrin Modified Coumarin

doi:10.6023/A1107292

Acta Chimica Sinica ›› 2012, Vol. 0 ›› Issue (05): 525-529 .DOI: 10.6023/A1107292 Next Articles

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α-环糊精修饰型香豆素的设计合成

江金强^a, 陈欣^a, 殷明^a, 王周平^b, 刘晓亚^a, 陈明清^a

a 江南大学化学与材料工程学院无锡 214122;
b 江南大学食品学院无锡 214122

投稿日期:2011-07-29 修回日期:2011-10-12 发布日期:2011-11-28
通讯作者: 江金强 E-mail:jiangjq@jiangnan.edu.cn
基金资助:
国家自然科学基金(Nos. 20704017, 50973044)、江苏省高校“青蓝工程”资助项目、中央高校基本科研业务费专项资金(No. JUSRP31003)资助项目.

Design and Synthesis of α-Cyclodextrin Modified Coumarin

Jiang Jinqiang^a, Chen Xin^a, Yin Ming^a, Wang Zhouping^b, Liu Xiaoya^a, Chen Mingqing^a

a School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122;
b School of Food Science and Technology, Jiangnan University, Wuxi 214122

Received:2011-07-29 Revised:2011-10-12 Published:2011-11-28
Supported by:
Project supported by the National Natural Science Foundation of China (NSFC) (under Grant Nos. 20704017, 50973044), the Qing Lan Project of Jiangsu Province and the Fundamental Research Funds for the Central Universities (No. JUSRP31003).

Using epichlorohydrin as the bridged unit, the water-soluble α-cyclodextrin (α-CD) was introduced to modify 7-hydroxy-4-methylcoumarin and prepare the novel α-cyclodextrin modified coumarin (α-CD-C), which was characterized by FTIR, ¹H NMR and LCMS. The photo-dimerization experiment showed that α-CD-C could photo-dimerize upon 365 nm irradiation, and then photo-de-crosslink upon the subsequent 254 nm irradiation. And by comparing the photo-dimerization degree upon 365 nm and 254 nm irradiation, it was concluded that the photo-dimerization reaction is only partially reversible.

Key words: coumarin, cyclodextrin, synthesis, UV, photo-dimerization

Cite this article

Jiang Jinqiang, Chen Xin, Yin Ming, Wang Zhouping, Liu Xiaoya, Chen Mingqing. Design and Synthesis of α-Cyclodextrin Modified Coumarin[J]. Acta Chimica Sinica, 2012, 0(05): 525-529 .

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1 Scott, R. T.; Allan, R. S.; Brian, J. L.; Timothy, E. L. Chem. Rev. 2004, 104, 3059

2 Boisde, P. M.; Meuly, C. Kirk-Othmer, Encyel. Chem. Technol. 1993, 7, 647.

3 Moeekli, P. Dyes Pigm. 1980, 1, 3.

4 Amendola, V. L.; Mangano, C.; Miller, H.; Pallavicini, P.; Perotti, A.; Taglietti, A. Angew. Chem., Int. Ed. 2002, 41,2553.

5 Wang, X. F.; Qu, Y.; Gu, F. Spec. Petrochem. 1999, 49, 52 (in Chinese). (王贤丰, 曲杨, 顾梵, 精细石油化工, 1999, 49, 52.)

6 Huang, C. H.; Li, F. Y.; Huang, Y. Y. Ultrathin Films for Optics and Electronics, 1st ed., Peking University Press, Beijing, 2001, p. 262 (in Chinese). (黄春辉, 李富友, 黄岩谊, 光电功能超薄膜, 第一版, 北京大学出版社, 北京, 2001, p. 262.)

7 Zhu, W. H.; Tian, H.; Zhu, S. Q. Prog. Chem. 2002, 14, 18 (in Chinese). (朱为宏, 田禾, 朱世琴, 化学进展, 2002, 14, 18.)

8 Charles, E. W. J. Am. Chem. Soc. 1959, 81, 1348.

9 Zhou, X.; Nimoth, J. B.; Pfeiffer, M.; Maennig, B.; Drechsel, J.; Werner, A.; Leo, K. Synth. Met. 2003, 138, 193.

10 Lee, M. T.; Yen, C. K.; Yang, W. P.; Chen, H. H.; Liao, C. H.; Tsai, C. H.; Chen, C. H. Org. Lett. 2004, 6, 1241.

11 Chen, Y.; Geh, J. L. Polymer 1996, 37, 4473.

12 Chen, Y.; Geh, J. L. Polymer 1996, 37, 4481.

13 Jiang, J. Q.; Qi, B.; Lepage, M.; Zhao, Y. Macromolecules2007, 40, 790.

14 Dahmane, S.; Lasia, A.; Zhao, Y. Macromol. Chem. Phys.2008, 209, 1065.

15 Babin, J.; Lepage, M.; Zhao, Y. Macromolecules 2008, 41,1246.

16 Fu, Q.; Cheng, L. L.; Zhang, Y.; Shi, W. F. Polymer 2008,49, 4981.

17 Jiang, J. Q.; Shu, Q. Z. Langmuir 2010, 26, 14247.

18 Shu, Q. Z.; Jiang, J. Q.; Chen, X.; Liu, X. Y.; Ni, Z. B.; Chen, M. Q. Acta Phys.-Chim. Sin. 2010, 26, 2845 (in Chinese). (舒巧珍, 江金强, 陈欣, 刘晓亚, 倪忠斌, 陈明清, 物理化学学报, 2010, 26, 2845.)

19 Jiang, J. Q.; Dai, P.; Zong, Y. W.; Liu, X. Y.; Zhang, S. W.; Chen, M, Q. Acta Phys.-Chim. Sin. 2009, 25, 2285 (in Chinese). (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, 2285.)

20 Nitin, C.; Arabinda, M.; Saumitra, S. J. Photochem. Photobiol. A: Chem. 2006, 177, 55.

21 Wang, B. Y.; Liu, X. Y.; Hu, Y. L.; Su, Z. X. Polym. Int.2009, 58, 703.

22 Dai, Z. H.; Wu, S. K. Acta Phys.-Chim. Sin. 1999, 15, 1076 (in Chinese). (戴赵华, 吴世康, 物理化学学报, 1999, 15, 1076.)

23 Gao, F.; Yang, Y. Y. Acta Phys.-Chim. Sin. 1999, 15, 550 (in Chinese). (高放, 杨永源, 物理化学学报, 1999, 15, 550.)

24 Li, X.; Wang, T.; Zhao, Y. X.; Wu, F. P. Photograph. Sci. Photochem. 2006, 24, 187 (in Chinese). (李雪, 王涛, 赵榆霞, 吴飞鹏, 感光科学与光化学, 2006,24, 187.)

25 Wang, T.; Wu, F. P.; Shi, M. Q.; Gao, F.; Yang, Y. Y. Acta Chim. Sinica 2004, 62, 527 (in Chinese). (王涛, 吴飞鹏, 施盟泉, 高放, 杨永源, 化学学报, 2004,62, 527.)

26 Hammond, G. S.; Stout, C. A.; Lamola, A. A. J. Am. Chem. Soc. 1964, 86, 31303.

27 Morrison, H.; Curtis, H.; McDowell, T. J. Am. Chem. Soc.1966, 88, 5415.

28 Liu, T. J.; Wu, S. K. Chem. J. Chin. Univ. 1996, 11, 1754 (in Chinese). (刘天军, 吴世康, 高等学校化学学报, 1996, 11, 1754.)

29 Liu, T. J.; Wu, S. K. Acta Phys.-Chim. Sin. 1996, 12, 677 (in Chinese). (刘天军, 吴世康, 物理化学学报, 1996, 12, 677.)

30 Zhu, A. P.; Wu, S. K. Photograph. Sci. Photochem. 1997,15, 151 (in Chinese). (朱爱平, 吴世康, 感光科学与光化学, 1997, 15, 151.)

31 Lehn, J. M. Supramolecular Chemistry-Concepts and Perspectives, Wiley-VCH Press, Wchlheim, 1995, pp. 1～271.

32 Awood, J. L.; Daries, J. E. D.; MacNicol, D. M.; Vögtle, F.; Lehn, J. M. Comprehensive Supramolecular Chemistry, Pergamon Press, Oxford, 1996, pp. 49～105.

33 Tong, L. H. Cyclodextrin Chemistry-Fundamentals and Applications, Science Press, Beijing, 2001, pp. 92～225 (in Chinese). (童林荟, 环糊精化学-基础与应用, 科学出版社, 北京,2001, pp. 92～225.)

34 Wenz, G.; Han, B. H.; Müller, A. Chem. Rev. 2006, 106,782.

35 Huang, F.; Gibson, H. W. Prog. Polym. Sci. 2005, 30, 982.

36 Nepogodiev, S. A.; Stoddart, J. F. Chem. Rev. 1998, 98,1959.

37 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. Cryst. Growth Des. 2004, 4,1431.

38 Martin, E. M.; Del, V. Process. Biochem. 2004, 39, 1033.

39 Ogoshi, T.; Harada, A. Sensors 2008, 8, 4961.

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

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

42 Connors, K. A. Chem. Rev. 1997, 97, 1325.

43 Wen, Z. L.; Zhang, Z. J. Analyst 1996, 121, 1119.

44 Lu, J. Z.; Zhang, Z. J. Analyst 1995, 120, 453.

45 Agjit, S.; Alarie, T. P.; Dinh, T. N. Talanta 1995, 42, 1567.

46 Paul, S.; Bate, S. Analyst 1994, 19, 181.

47 Loukas, Y. L.; Vyza, E. A.; Valiraki, A. P. Analyst 1995,120, 533.

48 Dang, Z.; Song, L. X.; Pan, S. Z.; Wang, M. Acta Phys.-Chim. Sin. 2009, 25, 1059 (in Chinese). (党政, 宋乐新, 潘淑臻, 王莽, 物理化学学报, 2009, 25,1059.)

49 Gao, Y. Y.; Liu, L. H.; Ou, Z. Z.; Li, Y.; Yang, G. Q.; Wang, X. S. Acta Phys.-Chim. Sin. 2010, 26, 495 (in Chinese). (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, 495.)

50 Dang, Z.; Song, L. X. Acta Phys.-Chim. Sin. 2010, 26, 1837 (in Chinese). (党政, 宋乐新, 物理化学学报, 2010, 26, 1837.)

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α-环糊精修饰型香豆素的设计合成

Design and Synthesis of α-Cyclodextrin Modified Coumarin

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