高等学校化学学报

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2-氨基-5-(对二甲氨基)苯基-1,3,4-噻二唑: Hg2+的选择性荧光传感分子

廖琴仙1,2, 李爱芳1, 黎朝1, 江云宝1   

  1. 1. 厦门大学化学化工学院化学系, 现代分析科学教育部重点实验室, 厦门 361005; 2. 厦门水务集团有限公司, 厦门 361008
  • 收稿日期:2008-10-06 修回日期:1900-01-01 出版日期:2008-12-10 发布日期:2008-12-10
  • 通讯作者: 江云宝

2-Amino-5-(p-dimethylamino)phenyl-1,3,4-thiadiazole as a Selective Fluorescent Chemosensor for Hg2+

LIAO Qin-Xian1,2, LI Ai-Fang1, LI Zhao1, JIANG Yun-Bao1*   

  1. 1. Department of Chemistry, College of Chemistry and Chemical Engineering, Key Laboratory of Analytical Sciences of Minster of Education, Xiamen University, Xiamen 361005, China; 2. Xiamen Water Group Co., Ltd., Xiamen 361008, China
  • Received:2008-10-06 Revised:1900-01-01 Online:2008-12-10 Published:2008-12-10
  • Contact: JIANG Yun-Bao

摘要: 设计合成了结构简单的分子内电荷转移荧光传感分子1,3,4-噻二唑类衍生物(1), 实现了水-乙醇(体积比1∶9)混合溶剂中Hg2+的荧光猝灭型选择性灵敏传感, 荧光猝灭常数达5.5×105 mol-1·L, Hg2+线性响应范围为5.0×10-6~5.0×10-5mol/L. 基于等摩尔连续变化法、红外光谱和核磁滴定实验结果提出了传感分子1与Hg2+的1∶1型结合模式, 其中1-位S原子和2-位胺N原子为Hg2+配位原子; 结合光谱变化讨论了Hg2+结合显著增强分子内电荷转移的荧光猝灭机理.

关键词: 荧光传感, 荧光猝灭, 1,3,4-噻二唑

Abstract: A structurally simple 2-amino-5-(p-dimethylamino)phenyl-1,3,4-thiadiazole(1) was designed and synthesized as a high selective fluorescent chemosensor for Hg2+ in H2O/EtOH(volume ratio 1∶9) solution. The selective quenching by Hg2+ of the fluorescence of compound 1 was rationalized in terms of the formation of a nonfluorescent Hg2+-1 complex with enhanced intramolecular charge transfer compared to compound 1 itself. The 1∶1 binding mode of compound 1 with Hg2+by its S atom and N atom of C-2 NH2 was proposed on the basis of Job plots, IR, and 1H NMR titrations. A linear fluorescent response was found for Hg2+ over 5.0×10-6 to 5.0×10-5 mol/L with a detection limit of 1.0×10-7 mol/L.

Key words: Fluorescent chemosensor, Hg2+, Fluorescence quenching, Intramolecular charge transfer, 1,3,4-Thiadiazole

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