A novel family of AIE-active <i>meso</i>-2-ketopyrrolyl BODIPYs: bright solid-state red fluorescence, morphological properties and application as viscosimeters in live cells

Yu, Changjiang; Huang, Zhenlong; Gu, Wei; Wu, Qinghua; Hao, Erhong; Xiao, Yi; Jiao, Lijuan; Wong, Wai Yeung

doi:10.1039/c9qm00154a

Cited by 36 publications

(33 citation statements)

References 79 publications

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“…This is resulting from the efficiently restricted ESDBR effect by the intermolecular H‐bonding interaction upon fluoro‐substitution. Furthermore, according to Förster–Hoffmann power‐law relationship, the relative PL intensity of AIEgens should increase in high‐viscous environment due to the limited molecular motions . We further carried out a viscosity study to confirm the ESDBR effect in the synthesized AIEgens (Figures c and d).…”

Section: Resultsmentioning

confidence: 99%

Planar AIEgens with Enhanced Solid‐State Luminescence and ROS Generation for Multidrug‐Resistant Bacteria Treatment

Min

et al. 2020

Angewandte Chemie

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Planar luminogens have encountered difficulties in overcoming intrinsic aggregation‐caused emission quenching by intermolecular π‐π stacking interactions. Although excited‐state double‐bond reorganization (ESDBR) can guide us on designing planar aggregation‐induced emission (AIE) luminogens (AIEgens), its mechanism has yet been elucidated. Major challenges in the field include methods to efficiently restrict ESDBR and enhance AIE performance without using bulky substituents (e.g., tetraphenylethylene and triphenylamine). In this study, we rationally developed fluoro‐substituent AIEgens with stronger intermolecular H‐bonding interaction for restricted molecular motions and increased crystal density, leading to decreased nonradiative decay rate by one order of magnitude. The adjusted ESDBR properties also show a corresponding response to variation in viscosity. Furthermore, their aggregation‐induced reactive oxygen species (ROS) generations have been discovered. The application of such planar AIEgen in treating multidrug‐resistant bacteria has been demonstrated in a mouse model. The relationship between ROS generation and distinct E/Z‐configurational stacking behaviors have been further understood, providing a design principle for synthesizing planar AIEgen‐based photosensitizers.

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Section: Resultsmentioning

confidence: 99%

Planar AIEgens with Enhanced Solid‐State Luminescence and ROS Generation for Multidrug‐Resistant Bacteria Treatment

Min

et al. 2020

Angewandte Chemie

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“…There is no doubt that high viscosity would restrict the intramolecular rotations and directly decrease the rapid non‐radiative decay. Thus, a turn on emission could be seen in more viscous media which might be applied in the measurement of viscosity or in the fast detection of the leaking oil [16,17] …”

Section: Resultsmentioning

confidence: 99%

“…Thus, a turn on emission could be seen in more viscous media which might be applied in the measurement of viscosity or in the fast detection of the leaking oil. [16,17] Thus, we tested the fluorescent response of these three compounds to the viscosity by simply increasing the fraction of glycerol in methanol. When adding glycerol into their dilute MeOH solutions, emissive spectra of compound 1 were slightly changed as the glycerol fraction changed from 0 to 90% ( Figure S17).…”

Section: Restriction Intramolecular Rotation and Viscosity Measurementmentioning

confidence: 99%

Preparation and Photoluminescent Properties of Three 5‐Amino Benzothiadiazoles (5‐amBTDs)

Wang

Lü

et al. 2020

Chemistry An Asian Journal

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Three DÀ A compounds were designed and synthesized based on a benzothiadiazole acceptor. Azepane (AP), iminodubenzyl (IDB) and iminostilbene (ISB) were used, respectively, as donors and installed on the 5-position of BTD to afford 1, 2 and 3, respectively. Their photophysical properties in different states (solution, film, crystal, and powder) are systematically investigated. Among them, AIEactive compounds 2 and 3 were found to have good sensitivity toward viscosity and display quite good linear relationship with an increase in viscosity. Compound 2 displayed dual emission in solutions which largely depended on the polarity of the solvent. Meanwhile, compound 2 exhibits a mechanochromic character with disappearance and reappearance of a dual-emissive peak induced by mechanical grinding and solvent fuming. Furthermore, these three compounds can be used in the fabrication of blue OLED devices.

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“…Thus, it is possible that a less bulky group (than phenyl) on meso -position of BODIPY with substituents on the 1,7-positions may allow the rotation in non-viscous media and thus might provide an alternative strategy for designing BODIPY based efficient micro-viscosity probes. Indeed, Yu et al recently reported a meso -2-ketopyrrolyl-derived BODIPY 10 as a new FMR containing substituents on the 1,7-positions (Figure 1J; Yu et al, 2019). The fluorescence lifetime (log τ) of BODIPY 10 has a linear relationship with viscosity (log η).…”

Section: Introductionmentioning

confidence: 99%

Functionalized BODIPYs as Fluorescent Molecular Rotors for Viscosity Detection

Miao

Hao

et al. 2019

Front. Chem.

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Abnormal changes of intracellular microviscosity are associated with a series of pathologies and diseases. Therefore, monitoring viscosity at cellular and subcellular levels is important for pathological research. Fluorescent molecular rotors (FMRs) have recently been developed to detect viscosity through a linear correlation between fluorescence intensity or lifetime and viscosity. Recently, 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (boron dipyrrins or BODIPY) derivatives have been widely used to build FMRs for viscosity probes due to their high rotational ability of the rotor and potentially high brightness. In this minireview, functionalized BODIPYs as FMRs for viscosity detection were collected, analyzed and summarized.

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A novel family of AIE-active meso-2-ketopyrrolyl BODIPYs: bright solid-state red fluorescence, morphological properties and application as viscosimeters in live cells

Abstract: AIE-active and bright solid-state red-emissive meso-2-ketopyrrolyl BODIPYs have been developed as viscosimeters in live cells for real-time quantification of intracellular viscosities.

Cited by 36 publications

References 79 publications

Planar AIEgens with Enhanced Solid‐State Luminescence and ROS Generation for Multidrug‐Resistant Bacteria Treatment

Planar AIEgens with Enhanced Solid‐State Luminescence and ROS Generation for Multidrug‐Resistant Bacteria Treatment

Preparation and Photoluminescent Properties of Three 5‐Amino Benzothiadiazoles (5‐amBTDs)

Functionalized BODIPYs as Fluorescent Molecular Rotors for Viscosity Detection

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