A Lawsone–DAMN based colorimetric chemosensor for rapid naked-eye detection of mercury(ii)

Abstract

We designed and synthesized a new colorimetric chemosensor L based on the combination of 3-hydroxy-1, 4-dioxo-1, 4dihydronaphthalene-2-carbaldehyde 2 and diaminomaleonitrile 3 moiety. The recognition abilities of the probe with a range of metal ions were evaluated and their optical properties have been systematically investigated. The chemosensor L exhibited well defined naked -eye visible color changes from yellow to pink for Hg 2+ in acetonitrile. Other ions, including Na + , Ca 2+ , CO 2+ , Ni 2+ , Cu 2+ , Mn 2+ , Sn 2+ , Hg 2+ , Fe 3+ , and Th 4+ had a negligible influence on the probe behaviour. The limit of detection (LOD) were 1.1x10 -7 M using the UV-vis changes. The selective recognition of Hg 2+ ions, it forms a 1:1 stoichiometric complex involving naphthoquinone hydroxyl and diaminomaleonitrile nitrogen functionality. The complex formations were proposed to be in 1:1 ratio based on Job plot, 1 H NMR titrations, ESI -mass spectrometry analysis and DFT calculations. Test strips based on L were fabricated, which could act as a convenient and efficient Hg 2+ test kits. The results consistently indicated that the Lawsone -DAMN was the ideal sensor, which can be utilised to monitor Hg 2+ in solution over a wide pH range. Graphical AbstractA highly sensitive and selective chemosensor L exhibited well defined naked -eye visible color changes from yellow to pink for Hg 2+ in acetonitrile. The selective recognition of Hg 2+ ions, it forms a 1:1 stoichiometric complex involving naphthoquinone hydroxyl and diaminomaleonitrile nitrogen functionality.

Green synthesis of new lawsone enaminones and theirZ/E(CC)-isomerization induced by organic solvent

“…It has been used as the starting material for the synthesis of a variety of biologically active compounds and materials with interesting properties. [22][23][24][25] In recent decades, it has been used in many reactions for the synthesis of various organic compounds. 26 Moreover, synthesis of aminonaphthoquinone Mannich base derivatives, as an interesting class of naphthoquinones, by multicomponent reactions of lawsone with a non-enolizable aldehyde and a primary or secondary amine via the Mannich reaction and their metal complexes using different conditions, and applications of these compounds has been reviewed.…”

Colorimetric detection of Hg2+ using a mixture of an anionic azo dye and a cationic polyelectrolyte in aqueous solution

“…). By calculating from the gradient ( k = 3.36 × 10, R 2 = 0.995) and σ = 1.63 × 10 −3 , the detection limit was found to be 1.46 μmol L −1 (equal to 0.292 mg kg −1 ), which is comparable to those (0.11–4.6 μmol L −1 ) of other colorimetric chemosensors for Hg 2+ (Table ) and lower than the maximum allowable level of Hg 2+ for food and animal feed regulated by the US Food and Drug Administration (1 mg kg −1 ) . As shown in Fig.…”

Recent progress in development of 2,3-diaminomaleonitrile (DAMN) based chemosensors for sensing of ionic and reactive oxygen species

“…The chemosensor (20) used in test strips was synthesized by the combination of diaminomaleonitrile and 3-hydroxy-1,4-dioxo-1,4- dihydronaphthalene-2-carbaldehyde. 55 The colorimetric sensing abilities of sensor (20) for Hg 2+ ion was again evaluated by UV-visible spectroscopy. It was observed that absorption bands of 20 at 335 nm and 481 nm were disappeared and new absorption bands at 421 nm and 595 nm were appeared on addition of Hg 2+ ion.…”