物理化学学报 >> 2011, Vol. 27 >> Issue (08): 1968-1974.doi: 10.3866/PKU.WHXB20110821

光化学和辐射化学 上一篇    下一篇

7-羟基-4-甲基-8-(4'-甲基哌嗪-1'-基)-亚甲基香豆素的光二聚行为

江金强, 龚韵华, 成浩, 刘晓亚, 张胜文, 徐晶   

  1. 江南大学化学与材料工程学院, 江苏 无锡 214122
  • 收稿日期:2011-05-04 修回日期:2011-06-03 发布日期:2011-07-19
  • 通讯作者: 江金强, 刘晓亚 E-mail:jiangjq@jiangnan.edu.cn. lxy@jiangnan.edu.cn
  • 基金资助:

    国家自然科学基金(20704017, 50973044), 江苏省高校“青蓝工程”项目及中央高校基本科研业务费专项资金(JUSRP31003)资助

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

JIANG Jin-Qiang, GONG Yun-Hua, CHENG Hao, LIU Xiao-Ya, ZHANG Sheng-Wen, XU Jing   

  1. School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, Jiangsu Province, P. R. China
  • Received:2011-05-04 Revised:2011-06-03 Published:2011-07-19
  • Contact: JIANG Jin-Qiang, LIU Xiao-Ya E-mail:jiangjq@jiangnan.edu.cn. lxy@jiangnan.edu.cn
  • Supported by:

    The project was supported by the National Natural Science Foundation of China (20704017, 50973044), Qing Lan Project of Jiangsu Province, China, and Scientific and Fundamental Research Funds for the Central Universities, China (JUSRP31003).

摘要:

通过Mannich反应在7-羟基-4-甲基香豆素的8-位上引入具有pH响应性能的4-甲基哌嗪的供电子哌嗪基团, 得到水溶性香豆素衍生物, 7-羟基-4-甲基-8-(4'-甲基哌嗪-1'-基)-亚甲基香豆素(HMPC), 利用哌嗪环上的叔胺给电子体系对酸碱的敏感特性调节HMPC的光二聚反应特征. 详细考察该香豆素衍生物在不同pH水溶液中的紫外光二聚性能, 紫外光谱分析显示, 通过调节HMPC水溶液的酸碱性可有效改变其紫外特征吸收; 在波长大于310 nm的紫外光照射下, 衍生物上的香豆素单元可进行光二聚, 并且紫外点光源光二聚反应实验表明, 其在中性水溶液中的反应速度最快, 其次为碱性条件中的反应, 最慢的则是酸性条件中的反应.

关键词: 香豆素, 哌嗪, pH-敏感, 叔胺基团, 给电子, 光二聚

Abstract:

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.

Key words: Coumarin, Piperazine, pH-sensitivity, Tertiary amine group, Electron donor, Photodimerization

MSC2000: 

  • O644