ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis and properties of an AIE fluorescent probe for Cu²⁺ detection based on ESIPT system

Jin Yan Shang, Yanbo Li, Kangni Chen, and Heping Li

Key Laboratory of Road Structure and Material of Ministry of Transport, School of Chemistry and Food Engineering, Changsha University of Science and Technology, Changsha, China

 

E-mail: lihepinghn@126.com

Received: 16 September 2020  Accepted: 21 November 2020

Abstract:

Abstract

The excessive accumulation of Cu²⁺ in the human body and the natural environment will endanger human health and break the balance of the ecosystem. Therefore, the development of a low-cost and rapid method to detect Cu²⁺ is of great significance to protect human health and the environment. In this study, we used electron-rich triphenylamine as the electron donor and AIE active core, coupled with the electron acceptor imine nitrogen, and further connected to the ESIPT active salicylaldimine unit, detection based on the ESIPT system a new AIE fluorescent probe 5-(diethylamino)-2-((E)-(((E)-4-(diphenylamino)benzylidene)hydrazono)methyl)phenol (DDP) was synthesized. DDP has strong fluorescence and can coordinate specifically with Cu²⁺ to form a copper complex and cause fluorescence quenching, thereby achieving the purpose of detecting Cu²⁺. The EDTA titration experiment was carried out on the DDP–Cu²⁺ solution, and the experimental results proved that the combination of DDP and Cu²⁺ is reversible. The interaction between DDP and Cu²⁺ rapidly forms a copper complex, which is approximately completed within 6 s. The detection limit of the probe is as low as 5.7 × 10^–8 M and it shows good stability in a weakly alkaline and weakly acidic environment, which provides necessary conditions for the detection of Cu²⁺ in a living environment. It is applied to the detection of Cu²⁺ in river water and lake water, showing a good linear relationship, indicating that DDP has the ability to detect Cu²⁺ in real water samples. Therefore, DDP is expected to become an effective tool for detecting Cu²⁺ in the environment and organisms.

Graphic abstract

Keywords: Synthesis; Property; AIE fluorescent probe; ESIPT; Copper(II)

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-020-01447-0

 

Chemical Papers 75 (5) 1851–1859 (2021)

© 2024 Chemical Papers