Naphthalene Flanked Diketopyrrolopyrrole: A New Functional Dye Based Optical Sensors for Monitoring Cyanide Ions in Water

Abstract

Cyanide (CN−) is one of the most hazardous ions to humans and the environment. Therefore, sensitive, and selective sensors for CN− monitoring are highly required. A novel chemosensor based on naphthalene flanked diketopyrrolopyrrole dye (TBC‐DPPN) is synthesized for the direct detection of CN− in water samples by naked eye and vibrational spectroscopy (UV–Vis and fluorescence). The electron deficient carbonyl group of the lactam ring of TBC‐DPPN undergoes a nucleophilic attack by the CN− thus causing the yellow color of the dye turn to colorless, and fluorescence of the dye at 527 nm to turn‐off. The mechanism of CN− sensing by the TBC‐DPPN sensor is confirmed by spectral measurements and density functional theory (DFT) calculations. The TBC‐DPPN sensor is utilized to determine the CN− by colorimetric and fluorescence methods in water down to 0.5 and 0.05 µm, respectively, which is well below the cut off limit of 1.9 µm that is recommended by the World Health Organization (WHO). Therefore, TBC‐DPPN can act as dual channel sensor with high selectivity and sensitivity for the determination of CN− in water.

2H-Pyran-2-one-Functionalized Diketopyrrolopyrrole Dye: Design, Synthesis, and Explosives Sensor

“…Literature search revealed that diketopyrrolopyrrole (DPP) has been extensively studied as a sensor for different analytes such as cations, anions, reactive oxygen species, pH, CO 2 , and H 2 S gas . Gholami et al reported recognition of CN – ions in water using naphthalene-flanked DPP as an optical sensor . Recently, DPP derivatives have been examined as biosensors in live-cell imaging. ,, To our surprise, very few reports are available in the literature for explosive sensors based on DPP .…”

“…21 Gholami et al reported recognition of CN − ions in water using naphthalene-flanked DPP as an optical sensor. 22 Recently, DPP derivatives have been examined as biosensors in live-cell imaging. 21,23,24 To our surprise, very few reports are available in the literature for explosive sensors based on DPP.…”

Synthesis of Novel Diketopyrrolopyrrole-Rhodamine Conjugates and Their Ability for Sensing Cu2+ and Li+

“…The use of diketopyrrolopyrrole (DPP) derivatives as fluorescent probes has been extensively explored in the last decade due to their high fluorescence quantum yields, exceptional photostability, and moderately high molar absorption coefficients [ 1 , 2 , 3 ]. The focus of these applications has been the tracing of biologically and environmentally important species, namely cations and anions [ 4 , 5 , 6 , 7 ]. The chemical versatility of the DPP skeletal unit allows for different functionalization to create a diverse range of DPP-based multifunctional dyes.…”

Synthesis and Optimization of Diphenyl Ether‐Based Receptors for the Selective Detection of Cyanide Ions in Neutral Semi‐Aqueous Medium

“…Several approaches for sensing cyanide ions have been reported in the literature. The nucleophilicity of the anion to attack carbonyl carbon, [21][22][23] alkenes [24][25][26] and playing around with proton abstraction are well documented. [27] However, the poor solubility of most organic ligands and the solvation of the cyanide ions in an aqueous medium limits the development of cyanide sensing.…”