Fluorescence Recognition of Hydrazine Driven by Neighboring Group Participation.

ABSTRACT

Hydrazine (N2H4) has toxic effects on the environment. Although a variety of reactive probes have been used to identify hydrazine, practical applications required continuous development of hydrazine fluorescent probes with improved performance. Here, we applied the neighboring group participation (NGP) to the design of a fluorescent probe for hydrazine. The probe exhibited a rapid response to N2H4 and strong anti-interference ability, with detection limited to 0.031 µmol/L. Theoretical calculation showed that the energy barrier could be reduced by NGP. The cyclic intermediate formed by the indole ring and the α-ester carbonyl group significantly reduced the activation energy of the reaction. Practically, the probe could detect hydrazine in actual water samples.