A rhodamine–bistriazole based fluorescent and colorimetric sensor containing a phenyl linker for Fe(III) detection

Wechakorn, Kanokorn; Chomngam, Sinchai; Eiamprasert, Utt; Kongsaeree, Palangpon

doi:10.1007/s11696-020-01349-1

Original Paper
Published: 17 September 2020

A rhodamine–bistriazole based fluorescent and colorimetric sensor containing a phenyl linker for Fe(III) detection

Kanokorn Wechakorn ORCID: orcid.org/0000-0001-6985-8214¹,
Sinchai Chomngam²,
Utt Eiamprasert¹ &
Palangpon Kongsaeree²

Chemical Papers volume 75, pages 883–892 (2021)Cite this article

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Abstract

A rhodamine-based fluorescent sensor bearing 1,2-phenylenediamine linked to a bistriazole moiety was designed and synthesized through the copper(I)-catalyzed click chemistry. The bistriazole-based sensor containing an aromatic linker was highly selective toward Fe³⁺, among other metal ions in MeCN/H₂O (1:9 v/v, pH 7.0). Upon the addition of Fe³⁺, the solution of the sensor changed from colorless to pink and fluorescence emission increased 614-fold, visually observed within 5 min. For the titration experiments, the absorption and fluorescence intensity were distinctly enhanced with the increasing concentrations of Fe³⁺ and the limit of detection (LOD) was calculated to be 0.15 μM. The binding ratio of the sensor–Fe³⁺ complex was a 1:1 ratio, confirmed by the Job’s plot. Besides, the optimized condition of the sensor for Fe³⁺ recognition was investigated in a pH range of 5.0–7.0.

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Acknowledgements

This work was supported by the Faculty of Science and Technology, Rajamangala University of Technology Thanyaburi. We would like to thank the central instrumentation laboratory of Rajamangala University of Technology Thanyaburi for NMR facility.

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Department of Chemistry, Faculty of Science and Technology, Rajamangala University of Technology Thanyaburi, Pathum Thani, 12110, Thailand
Kanokorn Wechakorn & Utt Eiamprasert
Department of Chemistry and Center for Excellence in Protein and Enzyme Technology, Faculty of Science, Mahidol University, Bangkok, 10400, Thailand
Sinchai Chomngam & Palangpon Kongsaeree

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Kanokorn Wechakorn
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Sinchai Chomngam
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Utt Eiamprasert
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Palangpon Kongsaeree
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Correspondence to Kanokorn Wechakorn.

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Wechakorn, K., Chomngam, S., Eiamprasert, U. et al. A rhodamine–bistriazole based fluorescent and colorimetric sensor containing a phenyl linker for Fe(III) detection. Chem. Pap. 75, 883–892 (2021). https://doi.org/10.1007/s11696-020-01349-1

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Received: 27 May 2020
Accepted: 09 September 2020
Published: 17 September 2020
Issue Date: March 2021
DOI: https://doi.org/10.1007/s11696-020-01349-1

Keywords

Fluorescent sensor
Rhodamine
Bistriazole
Click chemistry
Fe³⁺