A highly selective fluorescent probe for Al3+ based on bis(2-hydroxy-1-naphthaldehyde) oxaloyldihydrazone with aggregation-induced emission enhancement and gel properties

Chunbo Xing; Libo Hao; Libin Zang; Xiaodan Tang; Yuyan Zhao; Jilong Lu

doi:10.1016/j.saa.2019.117406

A highly selective fluorescent probe for Al³⁺ based on bis(2-hydroxy-1-naphthaldehyde) oxaloyldihydrazone with aggregation-induced emission enhancement and gel properties

Spectrochim Acta A Mol Biomol Spectrosc. 2020 Jan 5:224:117406. doi: 10.1016/j.saa.2019.117406. Epub 2019 Jul 19.

Authors

Chunbo Xing¹, Libo Hao¹, Libin Zang², Xiaodan Tang¹, Yuyan Zhao¹, Jilong Lu¹

Affiliations

¹ College of GeoExploration Science and Technology, Jilin University, Changchun, PR China.
² College of GeoExploration Science and Technology, Jilin University, Changchun, PR China. Electronic address: zanglb13@jlu.edu.cn.

PMID: 31351420
DOI: 10.1016/j.saa.2019.117406

Abstract

An efficient fluorescent probe, bis(2-hydroxy-1-naphthaldehyde) oxaloyldihydrazone (1), has been prepared for the selective sensing of Al³⁺ over other common metal ions in water-containing media. The 1:1 stoichiometry of 1 and Al³⁺ was determined from Job's plot and Benesti-Hildebrand plot. The binding constant was observed as 1.6×10⁵M^-1, and the limit of detection was found to be 0.36μM, which was far below the drinking water restriction of Al³⁺ by EPA (the maximum allowable value is 7.4μM). In addition, the inherent AIEE features of 1 were observed upon addition of water to DMSO solution due to the restriction of the intramolecular motion, which makes the molecular conformations rigid and planar. Moreover, 1 could act as a novel gelator to form thermo-reversible supramolecular organogel with significant green emission in DMSO-H₂O (v/v, 9:1) solution.

Keywords: AIEE; Aluminum ions; Bis(2-hydroxy-1-naphtaldehyde)oxaloyldihydrazone; Fluorescent probe; Organogel.