A dicyanoisophorone-based highly sensitive and selective near-infrared fluorescent probe for sensing thiophenol in water samples and living cells

Zhang, Yintang; Hao, Yuanqiang; Ma, Xiao‐Hua; Chen, Shu; Xu, Maotian

doi:10.1016/j.envpol.2020.114958

Cited by 34 publications

(13 citation statements)

References 76 publications

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“…However, after reacting with PhSH, the fluorescence of the solution increased significantly. According to previous studies, the reaction involves a three-step process (Figure S12a). First, the sulfhydryl group of PhSH performs a nucleophilic attack on the DNP moiety, then the released phenol oxygen and adjacent cyano group can spontaneously cyclize to form a pyran-2-imine structure; subsequently, the hydrolysis of the imine leads to the generation of a coumarin-derived product (Dye′-PhSH), which displays a strong fluorescence emission.…”

Section: Resultsmentioning

confidence: 95%

“…On the other hand, PhSH is highly toxic, and its detection is essential for environmental monitoring and protection. Up to now, many optical PhSH probes have developed by exploiting its unique reactivity for thiolyzing dinitrophenyl (DNP) moiety. − However, to the best of our knowledge, there are still no PEC methods for PhSH sensing. Coumarin derivatives are an important type of photoactive molecules and have been applied in various areas, including fluorescence detection and imaging, , organic light-emitting diodes, − and dye-sensitized solar cells. − Coumarin dyes can be synthesized by Perkin condensation, Knoevenagel condensation, Pechmann reaction, and metal-catalyzed cyclization .…”

Section: Resultsmentioning

confidence: 99%

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Target-Induced In Situ Formation of Organic Photosensitizer: A New Strategy for Photoelectrochemical Sensing

Hao

Dong

et al. 2022

ACS Sens.

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Small-molecule photosensitizers have great application prospects in photoelectrochemical (PEC) sensing due to their defined composition, diversified structure, and adjustable photophysical properties. Herein, we propose a new strategy for PEC analysis based on the target-induced in situ formation of the organic photosensitizer. Taking thiophenol (PhSH) as a model analyte, we designed and synthesized a 2,4-dinitrophenyl (DNP)-caged coumarin precursor (Dye-PhSH), which was then covalently coupled onto the TiO 2 nanoarray substrate to obtain the working photoanode. Due to the intramolecular photoinduced electron transfer process, Dye-PhSH has only a very weak photoelectric response. Upon reacting with the target, Dye-PhSH undergoes a tandem reaction of the detachment of the DNP moiety and the intramolecular cyclization process, which leads to a coumarin dye with a pronounced photoelectric effect, thus achieving a highly selective turn-on PEC response to PhSH. For the first time, this study was to construct a PEC sensor by exploiting specific organic reactions for the in situ generation of small molecule-based photoactive material. It can be anticipated that the proposed strategy will expand the paradigm of PEC sensing and holds great potential for detecting various other analytes.

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Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 99%

Target-Induced In Situ Formation of Organic Photosensitizer: A New Strategy for Photoelectrochemical Sensing

Hao

Dong

et al. 2022

ACS Sens.

Self Cite

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“…Additionally, small molecules also help to achieve higher fluorophore density and spatial resolution. Therefore, a large number of FOSMPs have been designed and applied to detect substances in various matrix [ 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 ]. Fluorescent organic nanoparticles (FONPs), which were designed with FOSMPs as fluorophores, show the ability to build a multifunctional biosensing platform through surface functionalization and drug encapsulation [ 52 ].…”

Section: Introductionmentioning

confidence: 99%

Fluorescent Organic Small Molecule Probes for Bioimaging and Detection Applications

et al. 2022

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The activity levels of key substances (metal ions, reactive oxygen species, reactive nitrogen, biological small molecules, etc.) in organisms are closely related to intracellular redox reactions, disease occurrence and treatment, as well as drug absorption and distribution. Fluorescence imaging technology provides a visual tool for medicine, showing great potential in the fields of molecular biology, cellular immunology and oncology. In recent years, organic fluorescent probes have attracted much attention in the bioanalytical field. Among various organic fluorescent probes, fluorescent organic small molecule probes (FOSMPs) have become a research hotspot due to their excellent physicochemical properties, such as good photostability, high spatial and temporal resolution, as well as excellent biocompatibility. FOSMPs have proved to be suitable for in vivo bioimaging and detection. On the basis of the introduction of several primary fluorescence mechanisms, the latest progress of FOSMPs in the applications of bioimaging and detection is comprehensively reviewed. Following this, the preparation and application of fluorescent organic nanoparticles (FONPs) that are designed with FOSMPs as fluorophores are overviewed. Additionally, the prospects of FOSMPs in bioimaging and detection are discussed.

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“…[9][10][11][12][13] Among numerous detecting methods of thiophenols, uorescent method was considered as the most powerful tool for thiophenols detection, because of the intrinsic advantages such as high selectivity and high sensitivity. [14][15][16][17][18][19] In these probes, 2,4-dinitrobenzenesulfonyl or 2,4-dinitrophenyl groups were employed as recognition moieties linked to various uorophores. [20][21][22][23][24][25] However, there are still some defects, such as high pH-dependence of the uorescence intensity, weak uorescence enhancement aer the addition of thiophenols, and relatively long response time, which limit the practical application of uorescent method in environmental samples.…”

Section: Introductionmentioning

confidence: 99%

A novel dibenzo[a,c]phenazine-based fluorescent probe for fast and selective detection of thiophenols in environmental water

2022

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A dicyanoisophorone-based highly sensitive and selective near-infrared fluorescent probe for sensing thiophenol in water samples and living cells

Cited by 34 publications

References 76 publications

Target-Induced In Situ Formation of Organic Photosensitizer: A New Strategy for Photoelectrochemical Sensing

Target-Induced In Situ Formation of Organic Photosensitizer: A New Strategy for Photoelectrochemical Sensing

Fluorescent Organic Small Molecule Probes for Bioimaging and Detection Applications

A novel dibenzo[a,c]phenazine-based fluorescent probe for fast and selective detection of thiophenols in environmental water

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