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Imidazole/Benzimidazole-Modified Cyclotriphosphazenes as Highly Selective Fluorescent Probes for Cu2+: Synthesis, Configurational Isomers, and Crystal Structures

Abstract

Configurational isomers (cis- and trans) of imidazole- or benzimidazole-modified cyclotriphosphazenes (3a,4a or 3b, 4b) were designed, synthesized and investigated as fluorescent probes for metal ions. The newly synthesized compounds were characterized by 1H and 31P NMR; and MALDI MS spectrometry. The configurations of geometric isomers were analyzed by X-ray crystallography and 31P NMR spectroscopy on addition of CSA. The photophysical behaviour and metal ion selectivity of compounds were investigated by UV/vis and fluorescence spectroscopies. Among the examined 20 metal ions, the fluorescence emission of the isomer mixtures were quenched by Cu+2 together with Fe2+, Fe3+, Zn2+ and Ni2+ ions, but each individual isomer (3a,b and 4a,b) exhibited on-off-type fluorescence response with high selectivity towards only Cu2+ with the low limits of detection ranging from 1.27 µM to 2.04 µM. The complex stoichiometries of 3a,b and 4a,b with Cu2+ were determined as 1:1 (L/M) using the method of continuous variation (Job’s plot) and density functional theory (DFT) calculation, moreover the complex formation of 4a with Cu2+ was unambiguously determined by X-ray crystallographic analysis that is consistent with the results obtained by the Job's plots as well as DFT.

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Publication details

The article was received on 29 Mar 2017, accepted on 13 Jun 2017 and first published on 13 Jun 2017


Article type: Paper
DOI: 10.1039/C7DT01134B
Citation: Dalton Trans., 2017, Accepted Manuscript
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    Imidazole/Benzimidazole-Modified Cyclotriphosphazenes as Highly Selective Fluorescent Probes for Cu2+: Synthesis, Configurational Isomers, and Crystal Structures

    A. Uslu, S. O. Tümay, A. Şenocak, F. Yuksel, E. Özcan and S. Yeşilot, Dalton Trans., 2017, Accepted Manuscript , DOI: 10.1039/C7DT01134B

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