Synthesis and Properties of Novel Fluorescence Probe Based on 1,8-Naphthalimide for Detection of Hydrogen Sulfide

Two fluorescence-enhanced probes, 4-(2,4-dinitrophenoxy)-N-(2-hydroxyethyl)-1,8-naphthalimide(NTE-1) and 4-(2,4-dinitrophenoxy)-N-[4-(2,4-dinitrophenoxy)phenyl]-1,8-naphthalimide(NTE-2), have been designed and synthesized for detection of H2S. 4-Hydroxy-1,8-naphthalimide as fluorophore in combination with 2,4-dinitrophenyl ether as H2S response site constructed the fluorescence probes. The consequences showed that both NTE-1 and NTE-2 displayed large red-shift(excess 100 nm) in absorption spectra and more than 30-fold fluorescence enhancement in response to H2S. Moreover, the dual site probe, NTE-2, displayed wider linear range between fluorescence intensity and concentration of H2S(0-40 mu mol/L) compared with single site probe, which can be applied to quantitative detection of high concentration of H2S. The photoinduced electron transfer(PET) response mechanism of probe was further studied by analyzing the distributions of molecular orbital. Importantly, the probes have potential practical applications in the detection of H2S.