Discovery of a highly selective and ultra-sensitive colorimetric fluorescent probe for malononitrile and its applications in living cells and zebrafish

Wang, Xin; Cheng, Siyu; Liu, Caiyun; Zhang, Yan; Su, Meijun; Rong, Xiaodi; Zhu, Hanchuang; Yu, Miaohui; Sheng, Wenlong; Zhu, Baocun

doi:10.1039/d1nj04815e

Cited by 5 publications

(2 citation statements)

References 56 publications

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“…However, there have been limited literature reports on this subject in recent years [21,23,24]. It is well-known that the compounds within the aldehyde group can often undergo Knoevenagel condensation reactions with malononitrile [25,26].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Novel Trisubstituted Olefin-Type Probe Molecules Containing N-Heterocycles and Their Application in Detection of Malononitrile

Chen,

Yu,

et al. 2024

Organics

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Recently, the construction of the trisubstituted olefin-type probe molecules has elicited the attention of many researchers. However, the synthesis of the trisubstituted olefin-type probes containing two N-heterocycles simultaneously has been rarely reported. In this study, starting from the inexpensive mucobromic acid 1 and N-heterocyclic compound 2, we first utilized a simple one-step reaction to synthesize a series of trisubstituted olefin-type compounds 3 simultaneously bearing with the structure of two N-heterocyclic rings in the absence of transition metal catalysts with a yield of 62–86%. The optimal reaction conditions were systematically explored, and the structure of the obtained compounds 3 were well characterized with 1H NMR, 13C NMR, X-ray single-crystal and HR-MS. The preliminary observation showed that, in the presence of base, mucobromic acid 1 reacts as its ring-opening structure, and the successive nucleophilic substitution reaction and Michael addition reaction can generate the target product 3. Considering that the aldehyde group in the molecular structure of the trisubstituted olefin-type compounds 3 may react with malononitrile, we carried out some relevant investigations so as to realize the visual detection of malononitrile. Interestingly, among the products, compounds 3a–3c can be prepared in portable test strips through a simple process and used to achieve the naked-eye detection of malononitrile in environmental systems as designed.

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Section: Introductionmentioning

confidence: 99%

“…It is well-known that the compounds within the aldehyde group can often undergo Knoevenagel condensation reactions with malononitrile [25,26]. Thus, if the colour of the compound as a probe is changed when the aldehyde group in the probe reacts with malononitrile, it can contribute to the naked-eye detection of malononitrile [24].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Trisubstituted Olefin-Type Probe Molecules Containing N-Heterocycles and Their Application in Detection of Malononitrile

Chen,

Yu,

et al. 2024

Organics

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Mitochondrial targeting fluorescent probe for specific detection of nickel ions and biological imaging

Yu,

Qian,

Shi

et al. 2023

Journal of Photochemistry and Photobiology A: Chemistry

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Comprehensive investigations of four ratiometric fluorescent chemosensors based on 4-(1H-imidazol-2-yl)benzaldehyde skeleton for malononitrile detection

Li,

Huang,

et al. 2024

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Discovery of a highly selective and ultra-sensitive colorimetric fluorescent probe for malononitrile and its applications in living cells and zebrafish

Abstract: As a highly toxic organic compound, malononitrile can cause serious harm to human health and environment. However, methods for rapid detection of malononitrile are rarely reported. Hence, this paper provides...

Cited by 5 publications

References 56 publications

Synthesis of Novel Trisubstituted Olefin-Type Probe Molecules Containing N-Heterocycles and Their Application in Detection of Malononitrile

Synthesis of Novel Trisubstituted Olefin-Type Probe Molecules Containing N-Heterocycles and Their Application in Detection of Malononitrile

Mitochondrial targeting fluorescent probe for specific detection of nickel ions and biological imaging

Comprehensive investigations of four ratiometric fluorescent chemosensors based on 4-(1H-imidazol-2-yl)benzaldehyde skeleton for malononitrile detection

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