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A novel colorimetric and fluorometric anion sensor based on BODIPY-calix[4]pyrrole conjugate

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Abstract

A novel fluorescent anion sensor 1 based on boradiazaindacenes (BODIPY) derivative was synthesized and its absorption and fluorescence properties were investigated in various solvents. 1 exhibited a red shift of absorption spectrum and fluorescence quenching in varying degree in the presence of F−, AcO−, H2PO4 − and Cl− due to multiple hydrogen bonding interactions between these anions and calix[4]pyrrole receptor. As an anion sensor in the visible region, 1 displayed the similar selectivity and sensitivity toward anions compared to the parent calix[4]pyrrole. However, 1 can be used as an effective dual responsive optical sensor for F− via chromogenical and fluorogenical signals.

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Acknowledgments

This work was supported by the National Natural Science Foundation of China (Grant No. 20972170 to S-J. Shao), the open fund of State Key Laboratory of Oxo Synthesis & Selective Oxidation (Grant No. OSSO2008kjk6 to S-J. Shao) and by the Natural Science Foundation of Gansu province (No. 096RJ2A033 to Y. Guo).

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Authors and Affiliations

  1. Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000, People’s Republic of China

    Yongjun lv, Jian Xu, Yong Guo & Shijun Shao

  2. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000, People’s Republic of China

    Shijun Shao

  3. Graduate School of the Chinese Academy of Sciences, Beijing, 100039, People’s Republic of China

    Yongjun lv

Authors
  1. Yongjun lv
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  2. Jian Xu
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  3. Yong Guo
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  4. Shijun Shao
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Correspondence to Shijun Shao.

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Fig. S1

UV–vis titration of sensor 1 (1 × 10−5 M in CH3CN) upon the addition of AcO− from 0 to 2.08 × 10−4 M. Inset: Nonlinear curve fitting as a function of [AcO−]. (TIFF 1143 kb)

Fig. S2

UV–vis titration of sensor 1 (1 × 10−5 M in CH3CN) upon the addition of H2PO4 − from 0 to 3.2 × 10−4 M. Inset: Nonlinear curve fitting as a function of [H2PO4 −]. (TIFF 1152 kb)

Fig. S3

UV–vis titration of sensor 1 (1 × 10−5 M in CH3CN) upon the addition of Cl− from 0 to 1.12 × 10−3 M. Inset: Nonlinear curve fitting as a function of [Cl−]. (TIFF 1060 kb)

Fig. S4

Changes in the emission spectrum of 1 (5 × 10−6 M in CH3CN) upon the addition of AcO− from 0 to 3.2 × 10−4 M. Inset: Nonlinear curve fitting as a function of [AcO−] monitored at 626 nm. Excitation was at 587 nm. (TIFF 658 kb)

Fig. S5

Changes in the emission spectrum of 1 (5 × 10−6 M in CH3CN) upon the addition of H2PO4 − from 0 to 8.48 × 10−4 M. Inset: Nonlinear curve fitting as a function of [H2PO4 −] monitored at 626 nm. Excitation was at 587 nm. (TIFF 892 kb)

Fig. S6

Changes in the emission spectrum of 1 (5 × 10−6 M in CH3CN) upon the addition of Cl− from 0 to 1.52 × 10−3 M. Inset: Nonlinear curve fitting as a function of [Cl−] monitored at 626 nm. Excitation was at 587 nm. (TIFF 823 kb)

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lv, Y., Xu, J., Guo, Y. et al. A novel colorimetric and fluorometric anion sensor based on BODIPY-calix[4]pyrrole conjugate. J Incl Phenom Macrocycl Chem 72, 95–101 (2012). https://doi.org/10.1007/s10847-011-9946-1

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  • DOI: https://doi.org/10.1007/s10847-011-9946-1

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