A naphthalimide-based chemodosimetric probe for ratiometric detection of hydrazine

A new naphthalimide-based probe was designed and synthesized for the rationmetric detection of hydrazine. The probe is designed in such a way that the intramolecular charge transfer (ICI') of the 4-hydroxynaphthalimide was masked by the 4-bromobutyrate moiety, and the selective deprotection of the 4-bromobutyrate group of the probe by hydrazine through a substitution-cyclisation-elimination process results in the recovery of the ICT of 4-hydroxynaphthalimide. Thus the probe can realize both calorimetric and fluorimetric detection of hydrazine in a ratiometric manner. The probe is highly selective toward hydrazine over other abundant interferences. The LOD (limit of detection) of the probe for N2H4 was calculated to be 0.27 mu M which is well below the safety level (10 ppb, 0.31 mu M) set by EPA. Notable, the probe loaded thin-layer-chromatography (TLC) plate could be successfully used to detect gaseous hydrazine. Moreover, the cell imaging studies demonstrated that the probe can be exploited to detect hydrazine in biological systems. (C) 2017 Elsevier B.V. All rights reserved.