A novel acylhydrazone-based derivative as dual -mode chemosensor for Al3+, Zn2+ and Fe3+ and its applications in cell imaging

作者:Liao, Zhuang; Liu, Yang; Han, Su-Fang; Wang, Dan; Zheng, Jian-Quan; Zheng, Xiang-Jun*; Jin, Lin-Pei
来源:Sensors and Actuators B: Chemical , 2017, 244: 914-921.
DOI:10.1016/j.snb.2017.01.074

摘要

An acylhydrazone-based derivative, 3-hydroxy-N'-(2-hydroxy-1-naphthalene methylene)-2 naphthalene hydrazide (H3L), was synthesized and characterized by elemental analyses, IR, H-1 NMR and mass spectrum. H3L is non-fluorescent in DMSO. But the fluorescence emission is enhanced obviously via the formation of aggregates in DMSO/H(2)0 mixture. The formed aggregates were confirmed by DLS and SEM. H3L is an aggregation-induced emission (AIE)-active fluorophore. H3L can act as a fluorescence sensor for Al3+ and Zn2+ in DMSO/H20 (v/v, 9/1) and THE/H(2)0 (v/v, 999/1), respectively. And H-3 L is also a naked-eye probe for Fe3+ in DMSO/H20 (v/v, 9/1). The binding stoichiometry of H3L to both Al3+ and Zn2+ is 1:1, but that to Fe3+ is 2:1. The metal complex species formed in the detection procedure are deduced by Job plot, spectroscopic titrations and ESI-MS to be [AIL(DMSO)(2)], IZn(HL)(H2O)] and [Fe(HL)(H2L)]. The detection limit is as low as 3.66 mu M for Al3+, '1.01 mu M for Zn2+ and 0.34 mu M for Fe3+. H3L can also be used to detect intracellular Al3+ and Zn2+. The sensing event might be attributed to a combinational effect of excited state intramolecular proton transfer (ESIPT) and chelation-enhanced fluorescence (CHEF) mechanism for selective detection of Al3+ and Zn2+ ions, and ligand-metal charge transfer (LMCT) mechanism for Fe3+ ion.