Citation: Li Yingjun, Zhang Nan, Jin Kun, Xu Yongting, Wang Siyuan, Zhou Xiaoxia. Novel Carbazole-Thiosemicarbazide Based Schiff-Base Probes for Cu²⁺[J]. Chinese Journal of Organic Chemistry, ;2017, 37(10): 2640-2646. doi: 10.6023/cjoc201704010 shu

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

Li Yingjun ^a,, ,
Zhang Nan ^a ,
Jin Kun ^b ,
Xu Yongting ^a ,
Wang Siyuan ^a ,
Zhou Xiaoxia ^a

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

Corresponding author: Li Yingjun, chemlab.lnnu@163.com
Received Date: 9 April 2017
Revised Date: 20 June 2017
Available Online: 4 October 2017
Fund Project: the Natural Science Foundation of Liaoning Province 20102126Project supported by the Natural Science Foundation of Liaoning Province (No. 20102126)

Figures(13)

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.
- carbazole,
- thiosemicarbazide,
- Schiff base,
- naked-eye recognition,
- Cu²⁺ fluorescence probe
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沈阳化工大学材料科学与工程学院沈阳 110142

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

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