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Download fileHighly Sensitive Bifunctional Probe for Colorimetric Cyanide and Fluorometric H2S Detection and Bioimaging: Spontaneous Resolution, Aggregation, and Multicolor Fluorescence of Bisulfide Adduct
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posted on 24.08.2017, 00:00 authored by Sumit
Kumar Patra, Sanjoy Kumar Sheet, Bhaskar Sen, Kripamoy Aguan, Debesh Ranjan Roy, Snehadrinarayan KhatuaA 4-methylbenzothiazole linked maleimide-based
single molecular
bifunctional probe 1 has been synthesized for the colorimetric
and fluorometric detection of highly competitive H2S and
cyanide ion in aqueous DMSO media. The probe 1 selectively
detected CN– under the UV–vis spectroscopy
through the rapid appearance of deep pink color. The bright pink color
developed due to ICT in the moderately stable cyano substituted enolate
intermediate. The absorbance titration of 1 with CN– revealed a new band at 540 nm and the nonlinear curve
fitting analysis showed good fit with 1:1 model. In fluorescence channel, 1 was found to be highly selective to H2S in 50%
aqueous buffer (pH 7). It exhibited ∼16-fold fluorescence intensity
enhancement at 435 nm after reaction with 1 equiv of H2S due to the inhibition of PET. The 1-SH adduct showed
TICT phenomenon and behaved like molecular rotor. It further displayed
aggregation behavior at higher concentration and excitation wavelength
dependent multicolor emission properties. Most interestingly, the
spontaneous resolution of chiral S-isomer of the
1-SH adduct occurred during crystallization. The cell imaging study
revealed the staining of the cell and multicolor emission in the presence
of H2S.
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Keywords
fluorescence intensity enhancementexcitation wavelengthaggregation behaviorMulticolor Fluorescencestainingenolatefluorometric detectioncell imaging studycyanochiral S4- methylbenzothiazoleinhibitionBisulfide Adductnonlinear curveappearanceSensitive Bifunctional Probefluorescence channelmaleimide-basedcolorimetricFluorometric H 2 S DetectionUVColorimetric CyanidepresencepHTICT phenomenonprobe 1crystallizationAggregationBioimagingCN1 equivH 2 Sspectroscopyisomerbifunctional probe 1DMSO mediacyanide ionconcentrationemission propertiesrotorSpontaneous Resolution435 nmabsorbance titration540 nm1- SH adductanalysismodel