Hydrogen-bond activated ESIPT in naphthalimide-based fluorescent probe for sensing volatile amines.

Amines levels present important indicative value in food safety and human health. Although they are involved in some normal physiological responses of the organism, their overproduction or intake may cause pathological responses. Herein, we report a recyclable visual packaging bag for volatile amines detections based on the naphthylamide derivative N-S and its positive PL characteristics. Specifically, handmade test strips based on compound N-S have been applied to fish freshness labeling, and the cyclic fumigation experiment shows its restorable PL effect and efficiency. The possible PL transfer mechanism of naphthylamide derivative N-S is uncovered by the density functional theory (DFT) calculation and titration mass spectrometer and 1H NMR. This work expands a conjugation in a molecule by hydrogen-bond activated ESIPT (H-ESIPT) and provides a portable detection method for volatile amines detection.

A novel 1,8-naphthalimide-based Cu2+ ion fluorescent probe and its bioimaging application.

A new 1,8-naphthalimide-based Schiff base compound, named as (Z)-2-butyl-6-(((2-hydroxyphenyl)imino)methyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (BHBD), has been simply synthesized with high yields. BHBD can be employed as a "turn-on" fluorescent probe for Cu2+ ion with high sensitivity, high selectivity and relatively low detection limit (0.48 × 10-6 M). The fluorescence emission of BHBD is very weak in H2O/THF (v/v: 7/3) mixture, which is significantly enhanced after addition of Cu2+ ion. The proposed mechanism is verified by 1H NMR, Job's plot and TOF-MS experiments. Anti-interference experiment, cytotoxicity assay and pH influence results indicated that BHBD meets the requirements of bioimaging. Therefore, BHBD has been successfully applied in detecting Cu2+ ion in HeLa cells.

A highly sensitive, fast responsive and reversible naphthalimide-based fluorescent probe for hypochlorous acid and ascorbic acid in aqueous solution and living cells.

It is very important to exploit real-time, ultrasensitive and specific visualization detection methods for hypochlorous acid/hypochlorite (HOCl/ClO-) in biological systems as they are the guardians of the human immune system against pathogens invasion. In our work, we designed a novel reversible naphthalimide-based fluorescent probe NAP-OH to recognize HClO/ClO- with a unique selective colorimetric and fluorescent response, a short response time (<8 s) and a high sensitivity (10.3 nM). In addition, NAP-OH exhibits a novel on-off-on fluorescence response to ClO-/ascorbic acid (AA) with good cycle stability. The fluorescence signal is quenched because HClO/ClO- oxidizes the subunit of NAP-OH to the segment 2,2,6,6-tetramethyl-1-oxo-piperidinium in NAP-O, which can be reduced by AA with the recovery of fluorescence. Finally, the confocal fluorescence imaging has been performed, which proves that NAP-OH can satisfactorily monitor intracellular endogenous and exogenous HClO/AA redox cycles.

An o-hydroxyl aldehyde structure based naphthalimide derivative: Reversible photochromic properties and its application in ClO- detection in living cells.

A bifunctional organic compound 2-butyl-6-hydroxy-1,3-dioxo-2,3-dihydro-1H-benzo[de] isoquinoline-5-carbaldehyde (BHC) with photochromic properties in solid state and probe detection for ClO- in complete water solution was synthesized and fully characterized. A 'white-yellow-white' reversible photochromic behavior could be observed when alternating UV/vis light irradiation on the solid BHC powder. Good fatigue resistance and adjustable bleaching rate were shown when heating conditions changes. In addition, BHC displayed a high selectivity and low detection limit (1.16 × 10-8 M) for ClO-. The photoluminescent fluorescence "on-off" recognition result can be easily identified and BHC has been tested for safely imaging living cells and detecting hypochlorite anion in vitro and vivo. A better water solubility of BHC effectively reduces damage caused by organic solvent in cell imaging progress.