Restriction of intramolecular bending (RIB) enables the quantitative design of AIEgens

Chi, Weijie; Dai, Jianfeng; Yan, Chenxu; Tan, Davin; Guo, Zhiqian; Liu, Xiaogang

doi:10.1039/d3tc01481a

Cited by 2 publications

(2 citation statements)

References 49 publications

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“…Moreover, the incorporation of targeting groups enables BODIPY-based fluorescent molecular rotors to identify alterations in the viscosity of diverse organelles present in cells. − It is noteworthy that certain BODIPY molecules dissipate energy through the adoption of bending conformation in the excited state. As the ambient viscosity increases, the intramolecular bending becomes constrained and tends toward a planar structure, showing higher fluorescence quantum yields. − Thus, the behavior of the BODIPY fluorophore could be governed by multiple mechanisms, including TICT, the bending mechanism,and most likely their combination. , …”

Section: Fluorescent Probes For Viscosity Detectionmentioning

confidence: 99%

Design and Application of Fluorescent Probes to Detect Cellular Physical Microenvironments

Ma,

Sun,

Xia

et al. 2024

Chem. Rev.

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The microenvironment is indispensable for functionality of various biomacromolecules, subcellular compartments, living cells, and organisms. In particular, physical properties within the biological microenvironment could exert profound effects on both the cellular physiology and pathology, with parameters including the polarity, viscosity, pH, and other relevant factors. There is a significant demand to directly visualize and quantitatively measure the fluctuation in the cellular microenvironment with spatiotemporal resolution. To satisfy this need, analytical methods based on fluorescence probes offer great opportunities due to the facile, sensitive, and dynamic detection that these molecules could enable in varying biological settings from in vitro samples to live animal models. Herein, we focus on various types of small molecule fluorescent probes for the detection and measurement of physical parameters of the microenvironment, including pH, polarity, viscosity, mechanical force, temperature, and electron potential. For each parameter, we primarily describe the chemical mechanisms underlying how physical properties are correlated with changes of various fluorescent signals. This review provides both an overview and a perspective for the development of small molecule fluorescent probes to visualize the dynamic changes in the cellular environment, to expand the knowledge for biological process, and to enrich diagnostic tools for human diseases.

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Section: Fluorescent Probes For Viscosity Detectionmentioning

confidence: 99%

Design and Application of Fluorescent Probes to Detect Cellular Physical Microenvironments

Ma,

Sun,

Xia

et al. 2024

Chem. Rev.

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“…Accordingly, the contribution of low-frequency vibrations (≤200 cm –1 ) to the excited-state reorganization energy (mainly due to the butterfly motions) is only 14.4% in DMAR-SY, compared to 38.2% in PTZR-DE (Figures S2 and S3). Low-frequency vibrations, accessible via thermal energy, could accelerate nonradiative decays and are detrimental to fluorescence quantum yields . The tailored motions in DMAR-SY and limited low-frequency vibration contributions to the reorganization energy could preserve a good quantum yield while amplifying the Stokes shift.…”

Section: Theoretical Calculationsmentioning

confidence: 99%

Auxochrome Dimethyl-Dihydroacridine Improves Fluorophores for Prolonged Live-Cell Super-Resolution Imaging

Ren,

Wang,

et al. 2024

J. Am. Chem. Soc.

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Superior photostability, minimal phototoxicity, red-shifted absorption/emission wavelengths, high brightness, and an enlarged Stokes shift are essential characteristics of top-tier organic fluorophores, particularly for long-lasting super-resolution imaging in live cells (e.g., via stimulated emission depletion (STED) nanoscopy). However, few existing fluorophores possess all of these properties. In this study, we demonstrate a general approach for simultaneously enhancing these parameters through the introduction of 9,9-dimethyl-9,10-dihydroacridine (DMA) as an electron-donating auxochrome. DMA not only induces red shifts in emission wavelengths but also suppresses photooxidative reactions and prevents the formation of triplet states in DMA-based fluorophores, greatly improving photostability and remarkably minimizing phototoxicity. Moreover, the DMA group enhances the fluorophores’ brightness and enlarges the Stokes shift. Importantly, the “universal” benefits of attaching the DMA auxochrome have been exemplified in various fluorophores including rhodamines, difluoride-boron complexes, and coumarin derivatives. The resulting fluorophores successfully enabled the STED imaging of organelles and HaloTag-labeled membrane proteins.

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Restriction of intramolecular bending (RIB) enables the quantitative design of AIEgens

Abstract: Fluorescent compounds with aggregation-induced emission (AIE) characteristics (or AIEgens) have garnered significant research interest for various applications. The establishment of new AIE mechanisms coupled with quantitative prediction power is crucial...

Cited by 2 publications

References 49 publications

Design and Application of Fluorescent Probes to Detect Cellular Physical Microenvironments

Design and Application of Fluorescent Probes to Detect Cellular Physical Microenvironments

Auxochrome Dimethyl-Dihydroacridine Improves Fluorophores for Prolonged Live-Cell Super-Resolution Imaging

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