Bis-BODIPY-based fluoride and cyanide sensor mediated by unconventional deprotonation of C−H proton

Saiyasombat, Worakrit; Eiamprasert, Utt; Chantarojsiri, Teera; Chainok, Kittipong; Kiatisevi, Supavadee

doi:10.1016/j.dyepig.2022.110643

Cited by 26 publications

(8 citation statements)

References 48 publications

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“…1), because it meets the design strategy mentioned above. 26 As expected, this probe can react with the analyte Cu 2+ to in situ generate a benzimidazole receptor providing an appropriate coordination environment that enhances metal ion binding efficiency in contrast to several previous examples of reaction-based chemosensors for copper. [27][28][29][30][31] To the best of our knowledge, there was only one report on this in situ receptor generation for Cu 2+ detection which was based on coppercatalyzed ring-closing of a diaminomaleonitrile moiety in the recognition process.…”

Section: Introductionmentioning

confidence: 67%

“…Preparation of BODIPY-NN BODIPY-NN was prepared through a Cu(I)-catalyzed azidealkyne cycloaddition (CuAAC) between azido-BODIPY and N,N 0 -dipropargylbenzene-1,2-diamine according to the previous report. 26 The analytically pure product was isolated via column chromatography in 63% yield. The detailed experimental procedures and characterization of BODIPY-NN are described in the ESI.…”

Section: Resultsmentioning

confidence: 99%

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A turn-on bis-BODIPY chemosensor for copper recognition based on the in situ generation of a benzimidazole–triazole receptor and its applications in bioimaging

et al. 2022

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Section: Introductionmentioning

confidence: 67%

Section: Resultsmentioning

confidence: 99%

A turn-on bis-BODIPY chemosensor for copper recognition based on the in situ generation of a benzimidazole–triazole receptor and its applications in bioimaging

et al. 2022

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“…Many BODIPY-based sensors following this principle have been reported for CN À detection. [22][23][24] However, these sensors face challenges such as the decomplexation of the -BF 2 unit from the BODIPY moieties. To address the single wavelength measurement, evaluation of CN À in the aqueous medium, and its application to biological samples, we have developed a 3-pyrrolyl BODIPY-based fluorescent sensor capable of ratiometric CN À detection.…”

Section: Introductionmentioning

confidence: 99%

An α-benzithiazolyl 3-pyrrolyl BODIPY probe for ratiometric selective sensing of cyanide ions and bioimaging studies

Behera,

Mohanty,

Ravikanth

2024

Phys. Chem. Chem. Phys.

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“…Cyanide ions are persistently generated in the environment through industrial processes such as plastic production, electroplating, metallurgy, and leather tanning. Moreover, industrial activities, such as organic reagent manufacturing, photography, and mining, release large amounts of cyanide into the environment. , Cyanide is a highly toxic chemical that can kill quickly, especially in mammals like humans. It affects the respiratory, cardiovascular, and nervous systems.…”

Section: Introductionmentioning

confidence: 99%

Off-On–Off Cascade Recognition of Cyanide, Mercury, and Aluminum Using N/5-Monosubstituted Rhodanines

Bayindir,

Hussein

2024

ACS Omega

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This study aims to synthesize N-and 5-monosubstituted rhodanine derivatives as ion-sensing organics and investigate their sensing abilities. Following an easy and green approach to synthesis, the anion-sensing properties of the rhodanines were studied using colorimetric detection and spectroscopic methods. As a result of studies, rhodanines are found to be highly solventcontrolled colorimetric and fluorescent cyanide, mercury, and aluminum sensors. The stoichiometry of the interaction between CN − and both probes was determined to be 1:1 using Job's plot analysis. The binding constants (K s ) of CN − to 5-arylRh and N-arylRh were calculated to be 3.25 × 10 4 and 7.07 × 10 4 M −1 , respectively, demonstrating their high affinity for cyanide ions. The limits of detections for the 5-arylRh and N-arylRh were also determined as 356 and 617 nM, respectively. In addition to detecting CN − , 5-arylRh also serves as a specific turn-off sensor for mercury and aluminum when cyanide and hydroxide are present. This enables the fluorescence intensity to be toggled on/off by alternating the addition of CN − /OH − and Hg 2+ /Al 3+ . Furthermore, the LOD values for Hg 2+ and Al 3+ with 5-arylRh−CN − and 5-arylRh−OH − were determined to be 414 nM and 1.35 μM, respectively. Furthermore, the turn-on binding mechanisms of 5-arylRh and N-arylRh with cyanide ions were elucidated, and the experimental band gap (highest occupied molecular orbital/least unoccupied molecular orbital) energy values corroborated the proposed mechanism. Additionally, the interaction mechanism of the probes with CN − was further investigated by using the 1 H NMR technique. Collectively, these findings suggest that 5-arylRh, N-arylRh, and 5-arylRh−CN − hold promise as selective and sensitive candidate sensors for CN − , Hg 2+ , and Al 3+ ions.

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Bis-BODIPY-based fluoride and cyanide sensor mediated by unconventional deprotonation of C−H proton

Cited by 26 publications

References 48 publications

A turn-on bis-BODIPY chemosensor for copper recognition based on the in situ generation of a benzimidazole–triazole receptor and its applications in bioimaging

A turn-on bis-BODIPY chemosensor for copper recognition based on the in situ generation of a benzimidazole–triazole receptor and its applications in bioimaging

An α-benzithiazolyl 3-pyrrolyl BODIPY probe for ratiometric selective sensing of cyanide ions and bioimaging studies

Off-On–Off Cascade Recognition of Cyanide, Mercury, and Aluminum Using N/5-Monosubstituted Rhodanines

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