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A highly selective fluorescent indicator for copper based on a boron complex

Posted on 26. February, 2015.

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Fluorescent organic dyes have been widely used in metal ion detection as fluorescent probes of high sensitivity and selectivity that allow reduced sample volume. Various ions can be successfully detected with a corresponding fluorescent compound, examples being: diketopyrrolopyrrole derivatives as fluorescent probes for Zn2+, 4‑aminoantipyrine for Al3+, and 4-(8-quinolyl)amino-7-nitro-2,1,3-benzoxadiazole for Hg2+.

The copper ion ranks third (behind Fe3+ and Zn2+) among the essential transition metal ions in the human body and plays a key role in a variety of fundamental physiological processes in organisms that range from bacteria to mammals.
Lack of Cu2+ can cause neurodegenerative diseases such as Menkes disease, Wilson disease, and Alzheimer’s disease. Therefore, the development of new selective fluorescent probes is necessary to detect the concentration of Cu2+. Several compounds have been used, such as N,N-bis(2-pyridylmethyl) amine, rhodamine chromene, and rhodamine. Boron complexes are the best-known fluorescent probes and have been widely applied in optical devices, biological sensing, light harvesting, and catalysis due to their valuable characteristics, such as: sharp, intense absorption, high molar absorption coefficients and high quantum yield. Boron complexes were also applied to detect different ions such as Zn2+, Hg2+, F and CN.

In the present work, the authors report a boron complex containing a 4-(diethylamino)-salicylaldehyde hydrazine structure, Boronil (1) can effectively detect Cu2+ in a water/THF (7 :3, v/v) solution using UV‑Vis absorption and fluorescence techniques; it showed significant fluorescence quenching in the presence of Cu2+ with markedly high sensitivity, selectivity and a reduced sample volume.

Read the full article in Journal of Chemical Research, Volume 39, Number 1, January 2015, pp. 36-40.

Authors: Jie Zhenga, Fang Huangb, Yujin Lia*, Qing Yea, Jianhong Jiaa, Liang Hana and Jianrong Gaoa
aState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, P.R. China
bDepartment of Pharmacology, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, P.R. China

Keywords: Cu2+, fluorescent indicator, boron complex, salicylaldehyde, hydrazine, fluorescent quenching

DOI: 10.3184/174751914X14190791988509

Image: The synthesis of Boronil