Far-red to near-infrared fluorescent probes based on silicon-substituted xanthene dyes for sensing and imaging

Zhao, Mei; Guo, Yushuang; Xu, Weina; Zhao, Yonggang; Xie, Hanyi; Li, Huijuan; Chen, Xiangfeng; Zhao, Ru-Song; Guo, Dian‐Shun

doi:10.1016/j.trac.2019.115704

Cited by 29 publications

(23 citation statements)

References 91 publications

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“…ABS probes for NIR-I imaging have been developed for diverse targets such as metal ions, 46 reactive oxygen species (ROS), 47 reactive nitrogen species (RNS), 48 thiols, 49 carbonyls, 50 and proteins. [51][52][53] ABS probes have been developed on a variety of dye platforms including but not limited to cyanine, 54 hemicyanine, 55 xanthene, 56 and donor-twoacceptor dyes. 57,58 Several excellent review articles that cover this in detail are available.…”

Section: Near Infrared-i Fluorescencementioning

confidence: 99%

New directions of activity-based sensing forin vivoNIR imaging

2021

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Section: Near Infrared-i Fluorescencementioning

confidence: 99%

New directions of activity-based sensing forin vivoNIR imaging

2021

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“…In order to convert them into the quinoid form [24,25], a small amount of HCl (37%) was added to a solution containing 5 or 6. The spectra were acquired (Figure 2) and two major changes were observed: (i) a change in coloration from colorless to orange with appearance of a new absorption band at 489 nm (5) and 485 nm (6), and (ii) the appearance of an emission band at 521 nm (5) and 508 nm (6). These changes indicate that the acidic pH led to the opening of the lactone to the quinoid form.…”

Section: Spectroscopic Characterizationmentioning

confidence: 99%

Functionalization of Rhodamine Platforms with 3-Hydroxy-4-pyridinone Chelating Units and Its Fluorescence Behavior towards Fe(III)

et al. 2022

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Functionalization of xanthene fluorophores with specific receptor units is an important topic of research aiming for the development of new analytical tools for biological sciences, clinical diagnosis, food and environmental monitoring. Herein, we report a new dihydrorosamine containing two active amino groups, which was functionalized with 3-benzyloxy-1-(3′-carboxypropyl)-2-methyl-4-pyridinone through an amide coupling strategy. Benzylated mono- and di-functionalized dihydrorosamine derivatives (H in position 9 of the xanthene) were obtained, but with modest reaction yields, requiring long and laborious purification procedures. Looking for a more efficient approach, rhodamine 110 was selected to react with the carboxypropyl pyridinone, enabling the isolation of the corresponding mono- and di-functionalized derivatives in amounts that depend on the excess of pyridinone added to the reaction. The structure of all compounds was established by 1H and 13C NMR, MS (ESI) and their absorption and emission properties were evaluated in dichloromethane. The fluorescence behavior of the debenzylated mono-rhodamine 110 derivative in the presence of Fe(III) was studied, making it an interesting fluorogenic dye for future optical sensing applications.

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“…Fluorescent probe has gained great attention in recent years owing to high sensitivity, high selectivity, fast response, low cost, and direct detection 12 . Especially, azobenzene fluorescent probe exhibits outstanding fluorescent quantum yield, light stability 13 , and chemical and thermal stability 14 .…”

Section: Introductionmentioning

confidence: 99%

A highly sensitive octopus-like azobenzene fluorescent probe for determination of abamectin B1 in apples

Guo

et al. 2021

Sci Rep

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The development of detecting residual level of abamectin B1 in apples is of great importance to public health. Herein, we synthesized a octopus-like azobenzene fluorescent probe 1,3,5-tris (5′-[(E)-(p-phenoxyazo) diazenyl)] benzene-1,3-dicarboxylic acid) benzene (TPB) for preliminary detection of abamectin B1 in apples. The TPB molecule has been characterized by ultraviolet–visible absorption spectrometry, 1H-nuclear magnetic resonance, fourier-transform infrared (FT-IR), electrospray ionization mass spectroscopy (ESI-MS) and fluorescent spectra. A proper determination condition was optimized, with limit of detection and limit of quantification of 1.3 µg L−1 and 4.4 μg L−1, respectively. The mechanism of this probe to identify abamectin B1 was illustrated in terms of undergoing aromatic nucleophilic substitution, by comparing fluorescence changes, FT-IR and ESI-MS. Furthermore, a facile quantitative detection of the residual abamectin B1 in apples was achieved. Good reproducibility was present based on relative standard deviation of 2.2%. Six carboxyl recognition sites, three azo groups and unique fluorescence signal towards abamectin B1 of this fluorescent probe demonstrated reasonable sensitivity, specificity and selectivity. The results indicate that the octopus-like azobenzene fluorescent probe can be expected to be reliable for evaluating abamectin B1 in agricultural foods.

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Far-red to near-infrared fluorescent probes based on silicon-substituted xanthene dyes for sensing and imaging

Cited by 29 publications

References 91 publications

New directions of activity-based sensing forin vivoNIR imaging

New directions of activity-based sensing forin vivoNIR imaging

Functionalization of Rhodamine Platforms with 3-Hydroxy-4-pyridinone Chelating Units and Its Fluorescence Behavior towards Fe(III)

A highly sensitive octopus-like azobenzene fluorescent probe for determination of abamectin B1 in apples

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