A systematic series of fluorescence chemosensors with multiple binding sites for Hg(ii) based on pyrenyl-functionalized cyclotriphosphazenes and their application in live cell imaging

Date

2018-09-07

Author

TÜMAY, SÜREYYA OĞUZ
USLU, AYLİN
Alidagi, Husniye Ardic
Kazan, Hasan Huseyin
Bayraktar, Cansu
Yolacan, Tutku
DURMUŞ, MAHMUT
YEŞİLOT, SERKAN

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A systematic series of fluorescence chemosensors (1-3) having one, two and three-metal binding sites based on cyclotriphosphazene derivatives bearing bis-, tetra- and hexakis-2-(pyren-1-yl methylene amino) phenoxy units, respectively, were designed, synthesized, and evaluated for their sensing behaviors toward metal ions using UV/Vis and fluorescence spectroscopies. Upon the addition of Hg2+ in both the absence and presence of competitive metal ions, the chemosensors revealed highly selective and sensitive turn-on emission enhancement based on the combined effects of chelation-enhanced fluorescence (CHEF), C?N isomerization and intramolecular pyrene excimer formation, as well as a color change from yellowish to colorless, which was readily detected by the naked eye. According to the Job plot method, the complexation ratios of chemosensors (1-3) with Hg2+ were found to be 1:1, 1:2 and 1:3 (ligand:metal), respectively, consistent with the proposed number of metal binding sites. Furthermore, the binding modes of chemosensors (1-3) with Hg2+ were supported by H-1 NMR spectroscopy. The increasing complexation ratios from 1:1 to 1:3 for chemosensors (1-3) enabled proportionally decreasing values for the detection limit (LOD) with 0.223 M, 0.114 M and 0.050 M, respectively. The cytotoxicity and fluorescence microscopy experiments also demonstrated that chemosensors (1-3) are non-cytotoxic, and can be used as fluorescence imaging sensors for Hg2+ in living cells.

Subject Keywords

Schiff-base, Heavy-metals, Turn-on, High-sensitivity, Living cells, HG2+ ions, Polymeric phosphazenes, Mercury speciation, Vapor generation, High selectivity

URI

https://hdl.handle.net/11511/68465

Journal

NEW JOURNAL OF CHEMISTRY

DOI

https://doi.org/10.1039/c8nj02482k

Collections

Department of Biology, Article

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Citation Formats

S. O. TÜMAY et al., “A systematic series of fluorescence chemosensors with multiple binding sites for Hg(ii) based on pyrenyl-functionalized cyclotriphosphazenes and their application in live cell imaging,” NEW JOURNAL OF CHEMISTRY, pp. 14219–14228, 2018, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/68465.