Abstract
• Synthesis of bay -functionalized unsymmetric trisubstituted PDI 1 and 2 is reported. • Ratiometric ‘turn-on’ absorbance (A 688 /A 560 ); fluorescence (F 670 /F 526 ) changes with H 2 S. • Low-cost solution-, solid-based test kits for the detection of ppm level of H 2 S gas. • We successfully applied PDI 1 for the intracellular detection of H 2 S in live A549 cells. We report the sustainable design for intracellular ratiometric ‘ turn-on ’ detection and discrimination of gaseous H 2 S and Cys using bay-functionalized trisubstituted PDI 1 and 2 . The two nitro groups were incorporated on PDI 1 and 2 as an effective target site for H 2 S, whereas presence of O-propargyl (PDI 1 ) and O-butyn (PDI 2 ) may be effective sites for H 2 S at high concentrations. This detection approach showed ratiometric ‘ turn-on ’ absorbance (A 688 /A 560 ) and fluorescence (F 670 /F 526 ) response associated with visual colour change from purple to green and green/red emission in the NIR region upon addition of H 2 S. These results were supported by current-voltage (I–V) plot, AFM, DLS studies and further augmented by isolation and characterization of intermediate product of reaction between PDI 1 and H 2 S. The application of PDI 1 and 2 as solution-based test kits for detection of 37.5 ppm H 2 S gas with naked eye colour change from purple to green to blue in 20s; PDI 1 adsorbed silica and TLC strips as solid-state test kits for detection of 150 ppm and 300–600 ppm H 2 S gas, respectively in 5 mins and exogenous detection of 150 and 750 µM H 2 S in A549 live cells have been demonstrated.
Published Version
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