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A α-cyanostilbene-modified Schiff base as efficient turn-on fluorescent chemosensor for Zn2+

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Abstract

A novel Schiff base derivative (Z)-3-(4-(hexyloxy)phenyl)-2-(4-((E)-2-hydroxybenzylidene amino)phenyl)acrylonitrile (L) was designed, synthesized and characterized. L was used as a Zn2+ selective, turn-on, fluorescent chemosensor with a detection limit of 0.1 μM in DMF. 1:1 stoichiometric complex formation of L wih Zn2+ was confirmed through fluorescent titration experiments and Job’s plot. The enhancement of fluorescence intensity of L with addition of Zn2+ is the consequence of the inhibited isomerization of the C=N bond, namely chelation-enhanced fluorescence (CHEF) effect.

α-Cyanostilbene-modified Schiff L was designed as a highly selective and sensitive zinc chemosensor. The complexation of L with Zn2+ enhanced the fluorescence intensity. This chemosensor could distinguish clearly Zn2+ from Cd2+, a frequently encountered trouble in the design for the Zn2+ fluorescent probes.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21101001 and 61107014), the Natural Science Foundation of Anhui Province (1208085MB21), the 211 Project of Anhui University, and the Team for Scientific Innovation Foundation of Anhui Province (2006KJ007TD).

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Authors and Affiliations

  1. Department of Chemistry, Key Laboratory of Functional Inorganic Materials of Anhui Province, Anhui University, Hefei, 230039, P. R. China

    AIXIANG DING, FANG TANG, TAO WANG & JIAXIANG YANG

  2. State Key Laboratory of Crystal Materials, Shandong University, **an, Shandong, 250100, P. R. China

    XUTANG TAO & JIAXIANG YANG

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  1. AIXIANG DING
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  2. FANG TANG
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  3. TAO WANG
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Correspondence to JIAXIANG YANG.

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Supplementary Information

Spectral data and calculated electron cloud distribution are given (figures S1–S5 and tables S1 and S2) which can be obtained from www.ias.ac.in/chemsci.

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DING, A., TANG, F., WANG, T. et al. A α-cyanostilbene-modified Schiff base as efficient turn-on fluorescent chemosensor for Zn2+ . J Chem Sci 127, 375–382 (2015). https://doi.org/10.1007/s12039-015-0787-0

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  • DOI: https://doi.org/10.1007/s12039-015-0787-0

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