A triphenylamine-based colorimetric and “turn-on” fluorescent probe for detection of cyanide anions in live cells

Wang, Shaodan; Xu, Hai; Yang, Qingbiao; Song, Yan; Li, Yaoxian

doi:10.1039/c5ra05807d

Cited by 31 publications

(11 citation statements)

References 53 publications

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“…[12][13][14] Derivative C2 was synthesized by condensation of 1,2,3,3-tetramethyl-3H-indol-1-ium with 2,7-azaindole-3-carboxaldehyde in ethanol (Scheme 2). 15 The structure of C2 was characterized by various spectroscopic and analytical studies ( Fig. S37-S39 in ESI †).…”

Section: Synthesis Of the Photosensitizers Based On Hemicyanine Derivmentioning

confidence: 99%

Exploring organic photosensitizers based on hemicyanine derivatives: a sustainable approach for preparation of amide linkages

Deol

Kumar

2018

RSC Adv.

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Section: Synthesis Of the Photosensitizers Based On Hemicyanine Derivmentioning

confidence: 99%

Exploring organic photosensitizers based on hemicyanine derivatives: a sustainable approach for preparation of amide linkages

Deol

Kumar

2018

RSC Adv.

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“…To calculate the limit of detection (LOD), the standard deviation of the blank measurements was determined by measuring the fluorescent intensity of probe 1 10 times [ 48 , 49 , 50 ]. Based on the equation (LOD = 3σ/m) and the fluorescence titration, the LOD was calculated to be 51 nM, which is much lower than the maximum level of cyanide anion (1.9 µM) in drinking water permitted by the WHO, suggesting its promising potential for the detection of low levels of cyanide anion in water samples.…”

Section: Resultsmentioning

confidence: 99%

A Biocompatible Colorimetric Triphenylamine- Dicyanovinyl Conjugated Fluorescent Probe for Selective and Sensitive Detection of Cyanide Ion in Aqueous Media and Living Cells

Zheng

Song

et al. 2017

Sensors

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A colorimetric and turn-on fluorescent probe 1 bearing triphenylamine-thiophene and dicyanovinyl groups has been synthesized and used to detect cyanide anion via a nucleophilic addition reaction. Probe 1 exhibited prominent selectivity and sensitivity towards CN− in aqueous media, even in the presence of other anions such as S2−, HS−, SO32−, S2O32−, S2O82−, I−, Br−, Cl−, F−, NO2−, N3−, SO42−, SCN−, HCO3−, CO32− and AcO−. Moreover, a low detection limit (LOD, 51 nM) was observed. In addition, good cell membrane permeability and low cytotoxicity to HeLa cells were also observed, suggesting its promising potential in bio-imaging.

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“…The specific synthesis steps for compounds A, 1 and 4 are described as follows or have been reported previously in the literature. [ 51–52 ]…”

Section: Methodsmentioning

confidence: 99%

A new highly selective fluorescent sensor based on a novel fluorophore for cyanide and its applications in bioimaging

Liu

et al. 2020

Luminescence

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A novel highly active fluorescence chemical sensor (TBI) for CN− was synthesized based on triphenylamine–benzothiazole as a new fluorophore, and was used for the first time as a fluorophore for detection of CN−. Fluorescence quantum yield of the probe clearly increased when using triphenylamine–benzothiazole as the group. The probe possessed good selectivity towards CN− and had anti‐interference ability over common ions. After adding CN−, the UV–visible spectrum of TBI changed clearly and underwent a dramatic colour change from red to colourless, which could be observed clearly by the naked eye. The limit of detection for CN− was calculated to be 2.62 × 10−8 M, which was well below the WHO cut‐off point of 1.9 μM. The novel probe displayed fast sensing of CN−. The detection mechanism was a nucleophilic addition reaction between CN− and a carbon atom –C = N– in indole salt. The π‐conjugation and intramolecular charge transfer (ICT) transition in the TBI molecule were destroyed by this addition, which resulted in a change of fluorescence before and after the addition of CN−. The mechanism was verified using theoretical calculation, 1H NMR titration, and mass spectra. In addition, the probe showed low cytotoxicity and could be used for biological imaging in HeLa cells.

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A triphenylamine-based colorimetric and “turn-on” fluorescent probe for detection of cyanide anions in live cells

Abstract: A triphenylamine–hemicyanine dye was developed as a colorimetric and turn-on fluorescent probe for detection of cyanide with high sensitivity and selectivity.

Cited by 31 publications

References 53 publications

Exploring organic photosensitizers based on hemicyanine derivatives: a sustainable approach for preparation of amide linkages

Exploring organic photosensitizers based on hemicyanine derivatives: a sustainable approach for preparation of amide linkages

A Biocompatible Colorimetric Triphenylamine- Dicyanovinyl Conjugated Fluorescent Probe for Selective and Sensitive Detection of Cyanide Ion in Aqueous Media and Living Cells

A new highly selective fluorescent sensor based on a novel fluorophore for cyanide and its applications in bioimaging

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