Hydrazine-Selective Fluorescent Turn-On Probe Based on Ortho-Methoxy-Methyl-Ether (<i>o</i>-MOM) Assisted Retro-aza-Henry Type Reaction
Hydrazine (N<sub>2</sub>H<sub>4</sub>) 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 to...
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MDPI AG
2019-10-01
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| Series: | Sensors |
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| Online Access: | https://www.mdpi.com/1424-8220/19/20/4525 |
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| author | Yuna Jung Nam Kyoo Park Jae Seung Kang Dokyoung Kim |
| author_facet | Yuna Jung Nam Kyoo Park Jae Seung Kang Dokyoung Kim |
| author_sort | Yuna Jung |
| collection | DOAJ |
| description | Hydrazine (N<sub>2</sub>H<sub>4</sub>) 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 <b>HyP-1</b>, for the detection of hydrazine, which is based on <i>ortho</i>-methoxy-methyl-ether (<i>o</i>-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 <b>HyP-2</b>, as the next-generation hydrazine probe. The sensing rational of <b>HyP-2</b> is based on the <i>o</i>-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 <b>HyP-2</b> 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. |
| first_indexed | 2024-04-13T08:40:39Z |
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| id | doaj.art-021c7cc1166b4f899382591baec3705b |
| institution | Directory Open Access Journal |
| issn | 1424-8220 |
| language | English |
| last_indexed | 2024-04-13T08:40:39Z |
| publishDate | 2019-10-01 |
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| series | Sensors |
| spelling | doaj.art-021c7cc1166b4f899382591baec3705b2022-12-22T02:53:54ZengMDPI AGSensors1424-82202019-10-011920452510.3390/s19204525s19204525Hydrazine-Selective Fluorescent Turn-On Probe Based on Ortho-Methoxy-Methyl-Ether (<i>o</i>-MOM) Assisted Retro-aza-Henry Type ReactionYuna Jung0Nam Kyoo Park1Jae Seung Kang2Dokyoung Kim3Department of Biomedical Science, Graduate School, Kyung Hee University, Seoul 02447, KoreaDepartment of Biomedical Science, Graduate School, Kyung Hee University, Seoul 02447, KoreaLaboratory of Vitamin C and Antioxidant Immunology, Department of Anatomy and Cell Biology, Seoul National University, College of Medicine, Seoul 03080, KoreaDepartment of Biomedical Science, Graduate School, Kyung Hee University, Seoul 02447, KoreaHydrazine (N<sub>2</sub>H<sub>4</sub>) 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 <b>HyP-1</b>, for the detection of hydrazine, which is based on <i>ortho</i>-methoxy-methyl-ether (<i>o</i>-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 <b>HyP-2</b>, as the next-generation hydrazine probe. The sensing rational of <b>HyP-2</b> is based on the <i>o</i>-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 <b>HyP-2</b> 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.https://www.mdpi.com/1424-8220/19/20/4525fluorescent probeoff-on responsehydrazine detectiondipolar fluorophoremolecular rotor |
| spellingShingle | Yuna Jung Nam Kyoo Park Jae Seung Kang Dokyoung Kim Hydrazine-Selective Fluorescent Turn-On Probe Based on Ortho-Methoxy-Methyl-Ether (<i>o</i>-MOM) Assisted Retro-aza-Henry Type Reaction Sensors fluorescent probe off-on response hydrazine detection dipolar fluorophore molecular rotor |
| title | Hydrazine-Selective Fluorescent Turn-On Probe Based on Ortho-Methoxy-Methyl-Ether (<i>o</i>-MOM) Assisted Retro-aza-Henry Type Reaction |
| title_full | Hydrazine-Selective Fluorescent Turn-On Probe Based on Ortho-Methoxy-Methyl-Ether (<i>o</i>-MOM) Assisted Retro-aza-Henry Type Reaction |
| title_fullStr | Hydrazine-Selective Fluorescent Turn-On Probe Based on Ortho-Methoxy-Methyl-Ether (<i>o</i>-MOM) Assisted Retro-aza-Henry Type Reaction |
| title_full_unstemmed | Hydrazine-Selective Fluorescent Turn-On Probe Based on Ortho-Methoxy-Methyl-Ether (<i>o</i>-MOM) Assisted Retro-aza-Henry Type Reaction |
| title_short | Hydrazine-Selective Fluorescent Turn-On Probe Based on Ortho-Methoxy-Methyl-Ether (<i>o</i>-MOM) Assisted Retro-aza-Henry Type Reaction |
| title_sort | hydrazine selective fluorescent turn on probe based on ortho methoxy methyl ether i o i mom assisted retro aza henry type reaction |
| topic | fluorescent probe off-on response hydrazine detection dipolar fluorophore molecular rotor |
| url | https://www.mdpi.com/1424-8220/19/20/4525 |
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