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Fluorescent sensors based on BODIPY derivatives for aluminium ion recognition: an experimental and theoretical study

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Abstract

Two BODIPY derivative sensors for metal ion recognition containing 10-(4-hydroxyphenyl) (L1) and 10-(3,4-dihydroxyphenyl) (L2) were synthesized in a one-pot reaction of benzaldehyde derivative and 2,4-dimethylpyrrole in the presence of trifluoroacetic acid as catalyst. The binding abilities between these sensors and 50 equivalents of Na+, K+, Ag+, Ca2+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Pb2+, Al3+ and Cr3+ ions were studied using UV–vis and fluorescent spectroscopic methods. Of all the metal ions tested, Al3+ ion showed the greatest decrease in intensity in the spectra of the sensors, and therefore Al3+ ion forms the strongest complex. The binding abilities of BODIPY receptors with Na+, Ag+, Ca2+, Co2+, Ni2+, Cu2+, Zn2+ and Al3+ ions were also investigated using density functional theory (DFT) calculations at B3LYP/LanL2DZ theoretical level. The calculated results point to the same conclusion. DFT calculations also provided the HOMO–LUMO energy levels, which can explain the spectrum change upon complexation.

Graphical structure, fluorescent spectra, frontier orbital energy diagrams and electron-transfer paths in sensor L1, and after attachment with Al3+ ion.

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Acknowledgments

The authors gratefully acknowledge the faculty of science, Mahasarakham University and the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Thailand for financial support of this research. Profound gratitude is also extended to the facility provided by Supramolecular Chemistry Research Unit and Department of Chemistry, Faculty of Science, Mahasarakham University, Maha Sarakham, Thailand.

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Authors and Affiliations

  1. The Center of Excellence for Innovation in Chemistry (PERCH–CIC) and Supramolecular Chemistry Research Unit, Department of Chemistry, Faculty of Science, Mahasarakham University, Maha Sarakham, 44150, Thailand

    Tasawan Keawwangchai, Nongnit Morakot & Banchob Wanno

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  1. Tasawan Keawwangchai
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  2. Nongnit Morakot
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  3. Banchob Wanno
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Corresponding authors

Correspondence to Nongnit Morakot or Banchob Wanno.

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Keawwangchai, T., Morakot, N. & Wanno, B. Fluorescent sensors based on BODIPY derivatives for aluminium ion recognition: an experimental and theoretical study. J Mol Model 19, 1435–1444 (2013). https://doi.org/10.1007/s00894-012-1698-3

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  • DOI: https://doi.org/10.1007/s00894-012-1698-3

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