Piperazine-tuned NBD-based colorimetric and fluorescent turn-off probes for hydrogen sulfide?

Analytical Methods Pub Date: 2018-06-20 DOI: 10.1039/C8AY00797G

Abstract

The piperazine ring is a very important factor in governing molecular structure to generate the special properties of a compound. New NBD-based fluorescent probes 1–3 were designed and synthesized for hydrogen sulfide (H2S) detection. Probe 1 showed high sensitivity and selectivity for H2S with a color change from yellow to pink for naked eye observation. However, the analogues (2 and 3) were response-negative toward H2S. In order to clarify the importance of the piperazine ring in the NBD-based H2S probe and the mechanism, the crystal structure of 1 was obtained and the piperazine ring was deemed to mediate H2S nucleophilic addition. In addition, probe 1 had limits of detection of 18.96 μM (UV) and 23.42 μM (FL), and the thiolysis rate for 1 was found to be 0.49 M?1 s?1. Living cell imaging results indicated that probe 1 could be utilized to trace intracellular H2S. This work has a great guiding role in the design of NBD-based fluorescent probes through a nucleophilic addition mechanism.

Graphical abstract: Piperazine-tuned NBD-based colorimetric and fluorescent turn-off probes for hydrogen sulfide
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