Latent turn-on fluorescent probe for the detection of toxic malononitrile in water and its practical applications

Jung, Yuna; Park, Nam Kyoo; Kang, Sangrim; Huh, Youngbuhm; Jung, Junyang; Hur, Junho K.; Kim, Dokyoung

doi:10.1016/j.aca.2019.10.015

Cited by 18 publications

(9 citation statements)

References 27 publications

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“…The 8-dialkylaminobenzo[ g ]coumarin motive has been subsequently explored by Ahn and co-workers in numerous contributions addressing, e.g., autofluorescence in deep tissue imaging , and discrepancy of fluorescence properties in solutions and in cells . The discovery of 8-dimethylamino-benzo[ g ]coumarin led to numerous papers exploring this dye as next generation fluorescent probes. − …”

Section: Introductionmentioning

confidence: 99%

Conformation of the Ester Group Governs the Photophysics of Highly Polarized Benzo[g]coumarins

Szychta

Koszarna

Banasiewicz

et al. 2023

JACS Au

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Photosensitizers that display “unusual” emission from upper electronically excited states offer possibilities for initiating higher-energy processes than what the governing Kasha’s rule postulates. Achieving conditions for dual fluorescence from multiple states of the same species requires molecular design and conditions that favorably tune the excited-state dynamics. Herein, we switch the position of the electron-donating NMe2 group around the core of benzo[g]coumarins (BgCoum) and tune the electronic coupling and the charge-transfer character of the fluorescent excited states. For solvents with intermediate polarity, three of the four regioisomers exhibit fluorescence from two different excited states with bands that are well separated in the visible and the near-infrared spectral regions. Computational analysis, employing ab initio methods, reveals that the orientation of an ester on the pyrone ring produces two conformers responsible for the observed dual fluorescence. Studies with solid solvating media, which restricts the conformational degrees of freedom, concur with the computational findings. These results demonstrate how “seemingly inconsequential” auxiliary substituents, such as the esters on the pyrone coumarin rings, can have profound effects leading to “anti-Kasha” photophysical behavior important for molecular photonics, materials engineering, and solar-energy science.

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Section: Introductionmentioning

confidence: 99%

Conformation of the Ester Group Governs the Photophysics of Highly Polarized Benzo[g]coumarins

Szychta

Koszarna

Banasiewicz

et al. 2023

JACS Au

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“…Thus, Jung et al developed a turn-on fluorescent probe, Mal-P1 (303), for malononitrile detection. 298 The LOD of Mal-P1 was 6.6 ppb, and the response time was 299 A decrease in fluorescence at 529 nm was observed, while a new fluorescence emission signal at 645 nm emerged. This probe exhibited an LOD of 27 nM and was employed to image malononitrile in living HeLa cells and zebrafish.…”

Section: Fluorescent Probes For the Target Enzymes And Metabolites Of...mentioning

confidence: 96%

“…Thus, Jung et al developed a turn-on fluorescent probe, Mal-P1 (303), for malononitrile detection. 298 The LOD of Mal-P1 was 6.6 ppb, and the response time was min. This probe was used to visualize malononitrile in living HeLa cells.…”

Section: Fluorescent Probes For the Target Enzymes And Metabolites Of...mentioning

confidence: 98%

Fluorescent probes for the detection of chemical warfare agents

Meng¹,

Sedgwick

Kwon

et al. 2023

Chem. Soc. Rev.

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“…First, we chose 6-(dimethylamino)-3-hydroxy-2-naphthaldehyde (compound 3) as a representative D-A type fluorophore, because its hydroxy moiety could be linked with AIEgen material without disturbing the character of dipolar backbone. The synthesis and distinguishable applications of compound 3 have been presented by our research group [22][23][24][25][26][27]. For an AIEgen material, we chose bromomethyl-functionalized TPE because it showed a typical property of AIEgen and has been widely used throughout various research fields [28][29][30].…”

Section: Materials Design Synthesis and Characterizationmentioning

confidence: 99%

Articulated Structures of D-A Type Dipolar Dye with AIEgen: Synthesis, Photophysical Properties, and Applications

Kim

Hur

et al. 2020

Materials

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Articulated structures of naphthalene-based donor (D)-acceptor (A) type dipolar dye and aggregation-induced emission luminogen (AIEgen) based on tetraphenylethylene (TPE) were synthesized, and their photophysical properties were analyzed for the first time. There are many fluorophore backbones, which have dipolar structure and AIEgen. However, there has been neither property analysis nor research that closely articulates DA and AIE through non-conjugation linker. We have therefore prepared two representative fluorophores; DA-AIE series (DA-AIE-M and DA-AIE-D), and characterized their UV/vis absorption and emission properties with quantum chemical calculations. In addition, we utilized the unique photophysical properties of DA-AIE-D for monitoring a trace of dimethyl sulfoxide (DMSO) in aqueous media, including real water samples.

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Latent turn-on fluorescent probe for the detection of toxic malononitrile in water and its practical applications

Cited by 18 publications

References 27 publications

Conformation of the Ester Group Governs the Photophysics of Highly Polarized Benzo[g]coumarins

Conformation of the Ester Group Governs the Photophysics of Highly Polarized Benzo[g]coumarins

Fluorescent probes for the detection of chemical warfare agents

Articulated Structures of D-A Type Dipolar Dye with AIEgen: Synthesis, Photophysical Properties, and Applications

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