A fast responsive chromogenic and near-infrared fluorescence lighting-up probe for visual detection of toxic thiophenol in environmental water and living cells

Fluorescent probes based on nucleophilic aromatic substitution reactions for reactive sulfur and selenium species: Recent progress, applications, and design strategies

“…Benzenesulfonamide and benzenesulfonate are the main reactive groups of benzenesulfonic acid [20] , [112] , [113] , [114] , [115] , [116] , [117] , [118] , [119] , [120] . RSS and RSeS can break the benzenesulfonamide or benzenesulfonate bond and become bound to the aromatic part of the detection group with the concomitant release of SO 2 .…”

Phenanthridine‐Based Donor/Acceptor Fluorescent Dyes: Synthesis, Photophysical Properties and Fluorometric Sensing of Biogenic Primary Amines

“…Though these methods are advantageous, they have some drawbacks such as specialized instrumentation, low sensitivity, low selectivity and short lifetime [33–34] . In recent years, fluorescence‐based detection methods are widely used as the biomedical, environmental monitoring, clinical testing, food safety testing and other fields as it has high sensitivity and selectivity [35–60] …”

Chemical Sensors towards Environmental Toxic Molecule Monitoring: Fluores-cent Probes for Detection of Thiophenol

“…[8,9] Recently, we one-step synthesized a NIR fluorescent probe NB-DN (675 nm) to detect thiolphenols and visualize detoxification process of H2O2 to thiophenol in HeLa cells. [10] Moreover, dinitrobenzene-sulfonyl ester-bearing probes possess relatively quicker responses than their dinitrobenzenesulfonyl amide counter-parts, [6a,9b] due to their faster SNAr reaction rate. Besides, the reported probes demonstrated pseudo-first-order reaction kinetics to thiophenol in solution.…”

“…Besides, the reported probes demonstrated pseudo-first-order reaction kinetics to thiophenol in solution. [9,10] Although the above remarkable progress was obtained, most of the reported probes still work in the mixture of buffer solution with organic solvent, and their synthetic routes are tedious and redundant. Moreover, rational design and synthesis of thiophenol-specific fluorescent probes with desired sensing properties and mechanisms are not achieved and still remain a big challenge.…”

“…To fulfill the optimized applicability, [11] as a future perspective, we suggested the following issues (Scheme 1) need to be further addressed: (1) Facile, low cost, green and high efficient synthesis procedures (e.g., one-pot or multi-component reactions) [12] need to be developed and employed to prepare new fluorescent probes; (2) To satisfy different thiophenol analytes and further optimize the sensing efficiency, new sensing mechanisms-based (e.g., AIEE, cascade-signaling, self-immolative) probes [13] need to be rationally designed and their molecular diversity need to be expanded; (3) Probe structure-sensing property relationships (SSPR), especially, the contribution of molecular factors (e.g., topology, linkage bonds, electrodonating/withdrawing groups (EDG/EWG), as well as flexibility/ rigidity) to the relevant sensing properties, need to be systematically studied; (4) For in vivo imaging and monitoring of thiophenols and toxicological analysis, new NIR probes (650-800 nm) possess low cytotoxicity, good water solubility and high cell membrane permeability, is highly demanded. Notably, in vivo NIR probes should avoid the risk of competition reaction of aliphatic biothiols (e.g., cysteine, homocysteine and glutathione) to thiophenols under enzyme catalysis in body fluid and cytoplasma; (5) For practical application, it is highly desirable to develop immobilized fluorescent probes by using functional polymers/dendrimers/nanomaterials as supporter or scavenger, through covalent or non-covalent surface modifica- (V/V = 3/2, pH = 7.4) [10] Scheme 1 Possible future directions for the R&D of thiophenol-specific fluorescent probes tion. [14] We believe that, in the near future, based on the dedicated works from chemists and biochemists worldwide, more and more efficient fluorescent probes for thiophenols detection will be created, optimized and employed in the fields of environmental analysis, eco-toxicology study, and in vivo bio-imaging.…”