Citation: JIANG Jin-Qiang, NG Yun-Hua, CHENG Hao, LIU Xiao-Ya, ZHANG Sheng-Wen, XU Jing. Photodimerization Behavior of 7-Hydroxy-4-methyl-8-(4'-methylpiperazin-1'-yl) Methylcoumarin[J]. Acta Physico-Chimica Sinica, ;2011, 27(08): 1968-1974. doi: 10.3866/PKU.WHXB20110821 shu

Photodimerization Behavior of 7-Hydroxy-4-methyl-8-(4'-methylpiperazin-1'-yl) Methylcoumarin

1.
School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, Jiangsu Province, P. R. China

Received Date: 4 May 2011
Available Online: 20 June 2011
Fund Project: 国家自然科学基金(20704017, 50973044) (20704017, 50973044)项目及中央高校基本科研业务费专项资金(JUSRP31003)资助 (JUSRP31003)

The water-soluble coumarin derivative 7-hydroxy-4-methyl-8-(4'-methylpiperazin-1'-yl) methylcoumarin (HMPC) was synthesized by the Mannich reaction between 7-hydroxy-4-methylcoumarin and N-methylpiperazine, which possesses an electrondonating piperazine group with pH responsivity. Since the piperazine group is a pH-sensitive electron donor, the resultant HMPC has interesting photophysical and photochemical properties in different pH solutions. We investigated the characteristic UV absorption and photodimerization behavior of the coumarin derivative. The characteristic UV absorption and also the photodimerization of HMPC, which was irradiated by UV light (λ>310 nm), was effectively changed in different pH solutions. The photodimerization experiments showed that in the neutral solution the dimerization reaction rate was most rapid followed by that in the alkaline solution and it was the slowest in the acidic solution at the same concentration.
- Coumarin,
- Piperazine,
- pH-sensitivity,
- Tertiary amine group,
- Electron donor,
- Photodimerization
1. [1]
  
  (1) Boisde, P. M.; Meuly, C.; Kirk, O. Encyclopedia of Chemical Technology; JohnWiley & Sons: New York, 1993; p 647.
2. [2]
  (2) Moeekli, P. Dyes and Pigments 1980, 1, 3
3. [3]
  (3) Ma, D. Q. Encyclopedia of Chemical Technology; Chemical Industry Press: Beijing, 1998; p 1047. [马德强. 化工百科全书. 北京: 化学工业出版社, 1998: 1047.]
4. [4]
  (4) Amendola, V. L.; Mangano, C.; Miller, H.; Pallavicini, P. A.; Taglietti, A. Angew. Chem. Int. Edit. 2002, 41 (14), 2553.
5. [5]
  (5) Schwander, H. Ullmann H P. 5th ed; VCH Verlagsges: Weinheim, 1991; p 27.
6. [6]
  (6) Raue, R. Ullmann. 5th ed; VCH Verlagsges:Weinheim, 1991; pp 151-164.
7. [7]
  (7) Wang, X. F.; Qu, Y.; Gu, F. Speciality Petrochemicals 1999, 1, 49. [王贤丰, 曲杨, 顾梵. 精细石油化工, 1999, 1, 49.]
8. [8]
  (8) Huang, C. H.; Li, F. Y.; Huang, Y. Y. Ultrathin Films For Optics and Electronics; Peking University Press: Beijing, 2001; p 262. [黄春辉, 李富友, 黄岩谊. 光电功能超薄膜. 北京: 北京大学出版社, 2001: 262.]
9. [9]
  (9) 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.]
10. [10]
  (10) Sherman,W. R.; Robins, E. Anal. Chem. l968, 40, 803.
11. [11]
  (11) Charles, E. Wheelock. J. Am. Chem. Soc. 1959, 81 (6), 1348.
12. [12]
  (12) Zhou, X.; Nimoth, J. B.; Pfeiffer, M.; Maennig, B.; Drechsel, J.; Werner, A.; Leo, K. Synth. Met. 2003, 138 (1-2), 193.
13. [13]
  (13) Lee, M. T.; Yen, C. K.; Yang,W. P.; Chen, H. H.; Liao, C. H.; Tsai, C. H.; Chen, C. H. Organic Letters 2004, 6 (8), 1241.
14. [14]
  (14) Ciamician, G.; Silber, P. Berichte Der Deutschen Chemischen Gesellschaft 1902, 35, 4128.
15. [15]
  (15) Scott, R. T.; Allan, R. S.; Brian, J. L.; Timothy, E. L. Chem. Rev. 2004, 104, 3059.
16. [16]
  (16) Delzenne, G. A. Europ. Polymer J. Supplement 1969, 55.
17. [17]
  (17) Schadt, M.; Seiberle, H.; Schuster, A. Nature 1996, 381, 212.
18. [18]
  (18) Kishore, G.; A. K. Macromolecules 1995, 28, 806.
19. [19]
  (19) Obi, M.; Morino, S.; Ichimura, K. Chem. Mater. 1999, 11, 656.
20. [20]
  (20) Jiang, J. Q.; Qi, B.; Martin, L.; Zhao, Y. Macromolecules 2007, 40, 790.
21. [21]
  (21) 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.]
22. [22]
  (22) Jackson, P. O.; O?Neill, M.; Duffy,W. L.; Hindmarsh, P.; Kelly, S. M.; Owen, G. J. Chem. Mater. 2001, 13, 694.
23. [23]
  (23) Jiang, J. Q.; Shu, Q. Z. Langmuir 2010, 26 (17), 14247.
24. [24]
  (24) Shu, Q. Z.; Jiang, J. Q.; Chen, X.; Liu, X. Y.; Ni, Z. B.; Chen, M. Q. Acta Phys. -Chim. Sin. 2010, 26 (10), 2845. [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 (10), 2845.]
25. [25]
  (25) 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.]
26. [26]
  (26) Wang, B. Y.; Liu, X. Y.; Hu, Y. L.; Su, Z. X. Polym. Int. 2009, 58, 703.
27. [27]
  (27) Nitin, C.; Arabinda, M.; Saumitra, S. J. Photochem. Photobiol. A: Chem. 2006, 118 (2), 55.
28. [28]
  (28) Dai, Z. H.;Wu, S. K. Acta Phys. -Chim. Sin. 1999, 15 (12), 1076. [戴赵华, 吴世康. 物理化学学报, 1999, 15 (12), 1076.]
29. [29]
  (29) Gao, F.; Yang, Y. Y. Acta Phys. -Chim. Sin. 1999, 15 (6), 550. [高放, 杨永源. 物理化学学报, 1999, 15 (6), 550.]
30. [30]
  (30) Li, X.;Wang, T.; Zhao, Y. X.;Wu, F. P. Photographic Science and Photochemistry 2006, 24 (3), 187. [李雪, 王涛, 赵榆霞, 吴飞鹏. 感光科学与光化学, 2006, 24 (3): 187.]
31. [31]
  (31) Wang, T.;Wu, F. P.; Shi, M. Q.; Gao, F.; Yang, Y. Y. Acta Chim. Sin. 2004, 62 (5), 527. [王涛, 吴飞鹏, 施盟泉, 高放, 杨永源. 化学学报, 2004, 62 (5), 527.]
32. [32]
  (32) Hammond, G. S.; Stout, C. A.; Lamola, A. A. J. Am. Chem. Soc. 1964, 86, 31303.
33. [33]
  (33) Morrison, H.; Curtis, H.; McDowell, T. J. Am. Chem. Soc. 1966, 88, 5415.
34. [34]
  (34) Liu, T. J.;Wu, S. K. Chem. J. Chin. Univ. 1996, 11, 1754. [刘天军, 吴世康. 高等学校化学学报, 1996, 11, 1754.]
35. [35]
  (35) Liu, T. J.;Wu, S. K. Acta Phys. -Chim. Sin. 1996, 12 (8), 677. [刘天军, 吴世康. 物理化学学报, 1996, 12 (8), 677.]
36. [36]
  (36) Zhu, A. P.;Wu, S. K. Photographic Science and Photochemistry 1997, 15 (2), 151. [朱爱平, 吴世康. 感光科学与光化学, 1997, 15 (2), 151.]
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