Design and synthesis of an AIE-active naphthaldehyde hydrazone-based ligand: mechanochromic, acidochromic, and sensing studies
Journal
MATERIALS ADVANCES
Date Issued
2026
Author(s)
Mandal, Ram Kumar
Haloi, Pankaj
Jain, Abhinav
Sutradhar, Sourav
Haribabu, Jebiti
Quezada, Diego
Moraga, Daniel
Barman, Pranjit
Abstract
A new multifunctional Schiff base material, 1-((E)-(((Z)-3,5-difluoro-2-hydroxybenzylidene)hydrazineylidene)methyl)naphthalen-2-ol (L2), was synthesized through a simple one-step condensation of 2-hydroxy-1-naphthaldehyde hydrazone and 3,5-difluorosalicylaldehyde. The ligand was characterized by FT-IR, 1H and 13C NMR, ESI-MS and single crystal X-ray diffraction. The crystal structure of L2 crystallizes in the monoclinic system with the space group P121/c1. The compound exhibited aggregation-induced emission (AIE) and excited-state intramolecular proton transfer (ESIPT) characteristics, along with reversible mechanochromic and acidochromic behavior. L2 exhibited a rapid, sensitive, and reversible colorimetric as well as fluorometric "turn-off" response for Cu2+ ions in aqueous media, displaying a 1 : 1 binding stoichiometry and an exceptionally low detection limit of 0.71 & micro;"M. The sensor L2 was effectively applied for Cu2+ detection in an on-site detection kit. Moreover, bioimaging studies demonstrated its excellent cell permeability, low cytotoxicity, and efficient Cu2+ sensing within living cells."


