Highly Sensitive Bifunctional Probe for Colorimetric Cyanide and Fluorometric H 2 S Detection and Bioimaging: Spontaneous Resolution, Aggregation, and Multicolor Fluorescence of Bisulfide Adduct

• Published in: Journal of organic chemistry Vol. 82; no. 19; pp. 10234 - 10246
• Main Authors: Patra, Sumit Kumar, Sheet, Sanjoy Kumar, Sen, Bhaskar, Aguan, Kripamoy, Roy, Debesh Ranjan, Khatua, Snehadrinarayan
• Format: Journal Article
• Language: English
• Published: United States 06.10.2017
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/acs.joc.7b01743

A 4-methylbenzothiazole linked maleimide-based single molecular bifunctional probe 1 has been synthesized for the colorimetric and fluorometric detection of highly competitive H S 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 H S in 50% aqueous buffer (pH 7). It exhibited ∼16-fold fluorescence intensity enhancement at 435 nm after reaction with 1 equiv of H S 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 H S.