Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (10): 2640-2646.DOI: 10.6023/cjoc201704010 Previous Articles     Next Articles



李英俊a, 张楠a, 靳焜b, 许永廷a, 王思远a, 周晓霞a   

  1. a 辽宁师范大学化学化工学院 大连 116029;
    b 大连理工大学精细化工国家重点实验室 大连 116012
  • 收稿日期:2017-04-09 修回日期:2017-06-20 发布日期:2017-07-04
  • 通讯作者: 李英俊
  • 基金资助:


Novel Carbazole-Thiosemicarbazide Based Schiff-Base Probes for Cu2+

Li Yingjuna, Zhang Nana, Jin Kunb, Xu Yongtinga, Wang Siyuana, Zhou Xiaoxiaa   

  1. a College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029;
    b State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012
  • Received:2017-04-09 Revised:2017-06-20 Published:2017-07-04
  • Contact: 10.6023/cjoc201704010
  • Supported by:

    Project supported by the Natural Science Foundation of Liaoning Province (No.20102126).

Three novel carbazole-thiosemicarbazides based Schiff-base were synthesized. The recognition ability of representive 2-((N-heptane-carbazol-3-yl)methylidene)hydrazine carbothioamide (L2) to metal ions was investigated by naked-eye, UV-Vis, fluorescence and mass spectra. The experimental results showed that this compound had a good water solubility and can be investigated in DMSO-H2O (V:V=6:4, Tris-HCl buffer, pH=7.0). The compound L2 in the DMSO-H2O displayed a dis-tinct color change from colorless to yellow upon the addition of Cu2+, other metal ions did not induce significant colour changes, which indicated that Schiff base L2 can be used as a probe with naked eye detection for Cu2+. The fluorescence spectra showed that the probe L2 was a high selective and sensitive "turn-off" fluorescence probe for Cu2+ in DMSO-H2O (V:V=6:4, Tris-HCl buffer, pH=7.0). The association constant between the probe L2 and Cu2+ was detected to be 3.42×104 L·mol-1, and the detection limit was calculated to be 8.96×10-6 mol·L-1. MS analysis showed a 1:1 binding stoichiometry between Cu2+ and L2. The detection limit of L2 for Cu2+ was far lower than the maximum allowable level of World Health Organization (WHO) limit (20 μmol·L-1) for drinking water.

Key words: carbazole, thiosemicarbazide, Schiff base, naked-eye recognition, Cu2+ fluorescence probe