Abstract

Naphthalenediimide derivatives have shown applications in the area of chemical sensors for anions due to their special optical and electrical properties. In the current work, NDI derivative having phenyl amine end group (PPD-NDI) has been synthesized and tested for sensitivity towards trifluoroacetic acid (TFA), hydrochloric acid (HCl), nitric acid (HNO <sub xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink">3</sub> ) and sulfuric acid (H <sub xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink">2</sub> SO <sub xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink">4</sub> ) for 1-65 mM concentrations. PPD-NDI displays reversible optical and visible sensitivity for detection of acids, specially, for HCl and TFA. PPD-NDI shows charge transfer band in the range of 500-600 nm in absorption spectra along with color change in presence of acid. To understand the mechanism of sensitivity, an exclusion method has been applied by analyzing other reference NDI molecules with different end groups and linkers. PPD-NDI shows selective sensitivity for TFA present in low concentration (1 mM) and HCl at all other concentrations. Binding constants for the association between PPD-NDI and acids are obtained from the Benesi Hildebrand plot and highest value is observed in case of TFA. The sensitivity of NDI derivatives can be very helpful in detection of acids in various industrial effluents from cloth, paper, refineries and in smelting industries. We have demonstrated the reversible lab-on paper strip testing experiment for detection of HCl acid by naked eye in low and high concentrations without need of any excitation light source.

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