Ferrocenyl-isoxazole Derivative: a Novel Electrochemical, Colorimetric and Fluorescent Multiple Signal Probe for Highly Selective Recognition of Cu2+ Ions

doi:10.1007/s40242-017-6239-2

Chemical Research in Chinese Universities ›› 2017, Vol. 33 ›› Issue (1): 31-35.doi: 10.1007/s40242-017-6239-2

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Ferrocenyl-isoxazole Derivative: a Novel Electrochemical, Colorimetric and Fluorescent Multiple Signal Probe for Highly Selective Recognition of Cu²⁺ Ions

ZHANG Zhiqin, HE Xinwei, SHANG Yongjia, YU Zhiyu, WANG Sufan, WU Fuli

Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P. R. China

Received:2016-06-12 Revised:2016-10-31 Online:2017-02-01 Published:2016-11-21
Contact: SHANG Yongjia,E-mail:shyj@mail.ahnu.edu.cn E-mail:shyj@mail.ahnu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.21172001, 21372008), the Natural Science Foundation of the Education Administration of Anhui Province, China(No.KJ2016A267), the Special and Excellent Research Fund of Anhui Normal University, China and the Doctoral Scientific Research Foundation of Anhui Normal University, China(No.2016XJJ110).

Abstract

Abstract:

In this paper, a novel compound 3-(2-quinolyl)-5-ferrocenyl-isoxazole(5) with high selectivity toward Cu²⁺ over other heavy and transition-metal(HTM) ions was designed and synthesized in good yields. The compound not only could be used as an electrochemical probe for Cu²⁺ with an anodic peak shift of Fe(II)/Fe(III) redox couple, but also could be a colorimetric and fluorescent probe due to the detectable change in color by naked eyes and a significant fluorescence quenching of monomeric anthracene moiety. This highly selective sensing of Cu²⁺ may be attributed to the unprecedented intermolecular electron-transfer reorganization after the oxidation of the first single electron of compound 5, as indicated by electrospray ionization mass spectrometry(ESI-MS) and density functional theory(DFT) calculation results. To the best of our knowledge, this class of compounds have rarely been reported in the field of molecular sensing. It may have a potential significance for the application of the ferrocenyl-isoxazole derivative in molecular recognition.

Key words: Ferrocene, Isoxazole, Receptor, Recognition, Cu²⁺

ZHANG Zhiqin, HE Xinwei, SHANG Yongjia, YU Zhiyu, WANG Sufan, WU Fuli. Ferrocenyl-isoxazole Derivative: a Novel Electrochemical, Colorimetric and Fluorescent Multiple Signal Probe for Highly Selective Recognition of Cu²⁺ Ions[J]. Chemical Research in Chinese Universities, 2017, 33(1): 31-35.

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Ferrocenyl-isoxazole Derivative: a Novel Electrochemical, Colorimetric and Fluorescent Multiple Signal Probe for Highly Selective Recognition of Cu²⁺ Ions

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