Hydrazine-selective fluorescent turn-on probe based on ortho-methoxy-methyl-ether (O-MOM) assisted retro-aza-henry type reaction

Yuna Jung, Nam Kyoo Park, Jae Seung Kang, Dokyoung Kim

Research output: Contribution to journalArticle

Abstract

Hydrazine (N2H4) is one of the most widely used industrial chemicals that can be utilized as a precursor of pesticides, pharmaceutics, and rocket propellant. Due to its biological and environmental toxicity with potential health risks, various sensing tools have been developed. Among them, fluorescence-based molecular sensing systems have been highlighted due to its simple-operation, high selectivity and sensitivity, and biocompatibility. In our recent report, we disclosed a ratiometric type fluorescent probe, called HyP-1, for the detection of hydrazine, which is based on ortho-methoxy-methyl-ether (o-MOM) moiety assisted hydrazone-formation of the donor (D)-acceptor (A) type naphthaldehyde backbone. As our follow-up research, we disclose a turn-on type fluorescent probe, named HyP-2, as the next-generation hydrazine probe. The sensing rational of HyP-2 is based on the o-MOM assisted retro-aza-Henry type reaction. The dicyanovinyl moiety, commonly known as a molecular rotor, causes significant emission quenching of a fluorescent platform in aqueous media, and its cleavage with hydrazone-formation, which induces a significant fluorescence enhancement. The high selectivity and sensitivity of HyP-2 shows practical explicabilities, including real-time paper strip assay, vapor test, soil analysis, and real water assay. We believe its successful demonstrations suggest further applications into a wide variety of fields.

Original languageEnglish
Article number4525
JournalSensors (Switzerland)
Volume19
Issue number20
DOIs
StatePublished - 2 Oct 2019

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Keywords

  • Dipolar fluorophore
  • Fluorescent probe
  • Hydrazine detection
  • Molecular rotor
  • Off-on response

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