Fluorescence signaling of BF3 species by transformation of an ESIPT dye to its difluoroboron adduct

Choi, Myung Gil; Jung, Yun-uk; Hong, Ja Min; Chang, Suk‐Kyu

doi:10.1016/j.snb.2017.05.098

Cited by 23 publications

(2 citation statements)

References 38 publications

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“…To date, ASPH derivatives have emission wavelengths shorter than 530 nm, but many of them display a high chemiluminescence property . 2-Aryl-benzothiazoles is a highly fluorescent motif, that has been used widely used in fluorescent molecular probes, molecular logic gates, and fundamental photophysical studies. ,− To realize a red-shift emission, 7-amino-6-sulfanylphthalazine-1,4(2H,3H)-dione (ASPH) as an intense chemiluminophore was reacted with 2-hydroxy-5-morpholinobenzaldehyde to form a new conjugated structure (HM-ASPH-PH). To further understand the photophysical properties of the HM-ASPH-PH, a computational study at the Cam-B3LYP/def2-TZVP level of DFT and Cam-B3LYP/def2-TZVP level of TD-DFT theory were conducted.…”

Section: Resultsmentioning

confidence: 99%

A Small Molecule Chemiluminophore with near 600 nm Emission for In Vivo Imaging of Myeloperoxidase and Inflammatory Diseases

Meng,

Zhang,

Tang

et al. 2024

Chemical & Biomedical Imaging

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Chemiluminescence has emerged as a vital tool for bioimaging in vivo. The red shift emission of chemiluminophores is extremely useful for in vivo bioimaging. In this work, the conjugation system of the luminol was extended to achieve a red-shifted emission (591 nm) along with excellent water solubility. The probe (HM-ASPH-PF) has a molecular weight of only 396.42, which contains a benzothiazole and a cyclic phthalhydrazide structure. The probe has been used for in vivo luminescence imaging of neutrophil-mediated acute liver injury, including alcoholic liver injury (ALI) and acute liver failure (ALF) in mice, by exploiting myeloperoxidase (MPO) as a biomarker. The activated neutrophils were specifically imaged by HM-ASPH-PF. HM-ASPH-PF was also successfully applied to monitor the neutrophils in livers in mouse models of ALI and ALF. Consequently, HM-ASPH-PF, as an effective luminescent small molecule that possesses a red-shift emission near 600 nm, has been applied for the detection of MPO in living cells and neutrophil-mediated acute liver injury. This work also demonstrates the applied potential of the luminescent probe for the diagnosis of other neutrophil-associated liver diseases.

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Section: Resultsmentioning

confidence: 99%

A Small Molecule Chemiluminophore with near 600 nm Emission for In Vivo Imaging of Myeloperoxidase and Inflammatory Diseases

Meng,

Zhang,

Tang

et al. 2024

Chemical & Biomedical Imaging

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“…Redox-active organic molecules are used in a wide variety of applications, ranging from energy storage, use as photochemical sensitizers, as homogeneous (electro)catalysts, and in biomedical applications. [1][2][3][4][5][6] The generation of charged organic molecules facilitates their solubility in aqueous and nonaqueous solvents. We are particularly interested in boron compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of new N-Heterocyclic-BF3 adducts and their reactivity vs water

Romo

Hossain

Woods

et al. 2022

Preprint

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Species derived from N-Heterocycles with BF3 Lewis acids generate adducts that are redox active. Here we report the synthesis and characterization of 5 N-Heterocycle-BF3 adducts: Py-(BF3)2, Q-(BF3)2, Ph-(BF3)2, TMQ-(BF3), and Dipy-(BF3)2. The new adducts were structurally characterized by 1H, 11B, and 19F NMR. As an example, the Q-BF3 adduct is stable in an inert environment but in the presence of oxygen or water, its voltammetric profile decays, suggesting chemical decomposition of the adduct. Furthermore, this decomposition is accompanied by the generation of BF4-. The crystalline structure of the reaction product of TMQ-(BF3) with traces of water was obtained, showing that the BF3 generates BF4- counterion. Based on our observations, we proposed a plausible reaction mechanism for the generation of BF4-.

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Tailoring Fluorescence Emission of Diketopyrrolopyrrole Dyes by an Aggregation‐induced Emission Coupled Excited‐state Intramolecular Proton Transfer Process

Wang

Tang

et al. 2018

Chemistry An Asian Journal

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Two diketopyrrolopyrrole derivatives (DPP1 and DPP2) are used for generating multiple luminescent colors (yellow-orange-red-deep red) in solution, nanoparticle, aggregate and solid states through an aggregation-induced emission (AIE) coupled excited-state intramolecular proton transfer (ESIPT) process. They are potentially useful for bioimaging due to their good biocompatibility and large Stoke shifts.

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Fluorescence signaling of BF3 species by transformation of an ESIPT dye to its difluoroboron adduct

Cited by 23 publications

References 38 publications

A Small Molecule Chemiluminophore with near 600 nm Emission for In Vivo Imaging of Myeloperoxidase and Inflammatory Diseases

A Small Molecule Chemiluminophore with near 600 nm Emission for In Vivo Imaging of Myeloperoxidase and Inflammatory Diseases

Synthesis and characterization of new N-Heterocyclic-BF3 adducts and their reactivity vs water

Tailoring Fluorescence Emission of Diketopyrrolopyrrole Dyes by an Aggregation‐induced Emission Coupled Excited‐state Intramolecular Proton Transfer Process

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