Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (9): 1780-1785.DOI: 10.6023/cjoc201405012 Previous Articles     Next Articles


马拓, 张瑾, 刘龙珠, 贺云, 张尊听   

  1. 教育部药用资源与天然药物化学重点实验室, 西北濒危药材资源开发国家工程实验室, 陕西师范大学化学化工学院, 西安 710062
  • 收稿日期:2014-03-08 修回日期:2014-03-24 发布日期:2014-06-03
  • 通讯作者: 张尊听
  • 基金资助:

    国家自然科学基金(No. 21372150)、高校基本科研业务费专项资金(No. GK261001095)资助项目.

Synthesis and Characterization of a Visualization and Water-Soluble Fluorescent Probe for Al3+

Ma Tuo, Zhang Jin, Liu Longzhu, He Yun, Zhang Zunting   

  1. Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062
  • Received:2014-03-08 Revised:2014-03-24 Published:2014-06-03
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21372150), and the Fundamental Research Funds for the Central Universities (No. GK261001095).

In order to improve the water-solubility of 4-(2'-hydroxyphenyl)-pyrimido[1,6-a]benzimidazole and 4-(2'-hydrx- yphenyl-4'-isopropoxy)-pyrimido[1,6-a]benzimidazoles, they were sulfonated in 98% H2SO4. Sodium 4-(2'-hydroxyphenyl)- pyrimido[1,6-a]benzimidazole-5-sulfonate (L1), sodium 4-(2'-hydroxyphenyl)-pyrimido[1,6-a]benzimidazole-3',5',10'-three- sulfonate (L2), sodium 4-(2',4'-dihydroxyphenyl)pyrimido[1,6-a]benzimidazol-5-sulfonate (L3) were obtained and indentified by the method of NMR, IR and MS. Fluorescence spectra of L1, L2 and L3 were detected, and they have the ESIPT effect with a large Stokes shift (175~225 nm). The structures of these compounds could be complex with Al3+, and the fluorescence spectra of Al3+ in L1, L2 and L3 were analyzed. The results showed that L2 exhibited good sensitivity selectivity to Al3+. The fluorescence of L2 was strengthened dramatically in the presence of Al3+. Other metal ions, such as Cu2+, Hg2+, K+, Mg2+, Na+, Ni2+, Pb2+, Zn2+, Cr3+, Fe3+ induced negligible fluorescence strengthening for L2 under the same conditions. When the concentration (0~20 μmol/L) of Al3+ was increased, the fluorescence intensity of L2 (10 μmol/L) was also increased. The Job’s plot and fluorescence titration indicated that the stoichiometry of L2-Al3+ was 1:2 and the detection limit of Al3+ was 0.073 μmol/L. Moreover, L2 was used for the visual detection of Al3+.

Key words: coordinate, aluminum ions, fluorescent probe, excited state intramolecular proton transfer (ESIPT), visual detection