Potential chiral fluorescent molecular probes based on an \u03b1,\u03b2-unsaturated ketone for anion detection

Congshu Li,Xiufang Xu,Xuefang Shang,Weitong Pan,Yingling Wang,Yanmei Chen,Lixia Liu,Tianyun Wang

doi:10.1038/s41598-019-55421-2

Congshu Li, Xiufang Xu + Show 6 more

Open Access

https://doi.org/10.1038/s41598-019-55421-2

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Abstract

A series of potential chiral compounds containing an α,β-unsaturated ketone was developed for anion detection. The interplay of compounds and biological momentous anions (Cl−, H2PO4−, I−, AcO−, HS−, F−, and Br−) was evaluated by UV-vis experiments, fluorescence experiments, and electrochemical tests. By comparison, compound 1 had the best selectivity and compound 5 had the strongest binding ability among the five compounds. And compound 5 had the highest sensitivity to H2PO4− among the measured anions, and it also can be applied to actual samples, the content of H2PO4− tested in the potassium dihydrogen phosphate fertilizer solution reached above 97.5% of the marked content, and the recovery rates were within the range of 98.5–99.1%, attesting that this method was reliable for the test of H2PO4− in fertilizer. Through HRMS titration, circular dichroism and optical rotation experiments, the probable interacted mechanism was proved that the interaction site was the C=C of the α,β-unsaturated ketone structure. In addition, the interacted mechanism was researched from the perspective of chirality. Furthermore, theoretical investigation analysis was introduced to reveal that the roles of molecular frontier orbitals in molecular interplay were determined. Therefore, this series of potential chiral compounds has potential application prospects in anion recognition.

Highlights

A series of potential chiral compounds containing an α,β-unsaturated ketone was developed for anion detection
With the increasing attention on the safety and environmental problems with using radioactive probes and the advantages of high sensitivity and good selectivity, fluorescent probes have been widely used in molecular recognition
In view of the important role of anions in nature, a great deal of effort has been made within the field of supramolecular chemistry to devise and synthesize receptors capable of selectively identifying anions[7,8,9,10]

Summary

Introduction

A series of potential chiral compounds containing an α,β-unsaturated ketone was developed for anion detection. Theoretical investigation analysis was introduced to reveal that the roles of molecular frontier orbitals in molecular interplay were determined This series of potential chiral compounds has potential application prospects in anion recognition. There are few reports on potential chiral fluorescent molecular probes used to detect anions. It is very important to use potential chiral fluorescent molecular probes to selectively detect anions. A string of potential chiral compounds containing an α,β-unsaturated ketone structure was designed and synthesized (Scheme 1). The synthetic compounds displayed a high combination capacity for AcO−, HS−, F−, H2PO4− in the sensing of different anions by UV-vis, fluorescence, electrochemical, circular dichroism and optical rotation experiments. The crystal of compound 1 was obtained, which provided the foundation for the host-guest interaction

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