Tetraphenylpyrazine-based luminogens with full-colour emission

Pan, Lingxiang; Cai, Yuanjing; Wu, Haozhong; Zhou, Fan; Qin, Anjun; Wang, Zhiming; Tang, Ben Zhong

doi:10.1039/c7qm00551b

Cited by 50 publications

(21 citation statements)

References 55 publications

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“…While for TPE‐IQ‐TPA, due to stronger electron‐donating capability of TPA, the electron cloud of HOMO was transferred to the triphenylamine part, implying its intramolecular charge transfer (CT) process was different from the other three molecules above. Luckily, the HOMOs of these TPE‐IQ‐based AIEgens were all mainly localized on typical restriction of intramolecular rotation (RIR) blocks (triphenylethylene or triphenylamine), so their AIE features were expected according to previous reports …”

Section: Resultsmentioning

confidence: 54%

Structural Modification Orientated Multifunctional AIE Fluorescence Probes: Organelles Imaging and Effective Photosensitizer for Photodynamic Therapy

Chen

Zhang

Wang

et al. 2019

Advanced Optical Materials

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Luminogens with aggregation‐induced emission feature (AIEgens) are highly demanded because of its excellent performance in fluorescent bioprobes. In this work, three AIEgens based on tetraphenylethylene isoquinolinium (TPE‐IQ) derivatives by introducing different electron donor and sterically hindered groups to replace the phenyl ring of the isoquinolinium core are prepared in a one‐pot reaction with a high yield and characterized systematically. By the analysis of photophysical properties and theoretical calculations, the structure‐property relationships among them become clear. Although they all inherit AIE feature as expected, these similar structural AIEgens present different organelle‐targets, which is attributed to their different cellular uptake way and energy barrier to cell membrane by detailed experiments. In addition, these TPE‐IQ‐based AIEgens are potential candidates for photodynamic therapy originating from their activities of generating reactive oxygen species under visible light irradiation.

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Section: Resultsmentioning

confidence: 54%

Structural Modification Orientated Multifunctional AIE Fluorescence Probes: Organelles Imaging and Effective Photosensitizer for Photodynamic Therapy

Chen

Zhang

Wang

et al. 2019

Advanced Optical Materials

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“…1 H-NMR analysis confirmed the modification efficiency up to 98.6% (). After that, the aggregation-induced emission (AIE) characteristics of PDMA-TPE were investigated in water/THF mixtures with diverse water contents ( f W ), from 0 to 99% [45]. PDMA-TPE was almost non-emissive in THF solution in molecular state, mainly due to that the rotational motion of phenyl rings and double bonds in the terminal TPE unit was free to contribute nonradiative decay, leading to non-emission in solution state [46, 47].…”

Section: Resultsmentioning

confidence: 99%

A Simple Approach to Bioconjugation at Diverse Levels: Metal-Free Click Reactions of Activated Alkynes with Native Groups of Biotargets without Prefunctionalization

Zhao

et al. 2018

Research

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The efficient bioconjugation of functional groups/molecules to targeted matrix and bio-related species drives the great development of material science and biomedicine, while the dilemma of metal catalysis, uneasy premodification, and limited reaction efficiency in traditional bioconjugation has restricted the booming development to some extent. Here, we provide a strategy for metal-free click bioconjugation at diverse levels based on activated alkynes. As a proof-of-concept, the abundant native groups including amine, thiol, and hydroxyl groups can directly react with activated alkynes without any modification in the absence of metal catalysis. Through this strategy, high-efficient modification and potential functionalization can be achieved for natural polysaccharide, biocompatible polyethylene glycol (PEG), synthetic polymers, cell penetrating peptide, protein, fast whole-cell mapping, and even quick differentiation and staining of Gram-positive bacteria, etc. Therefore, current metal-free click bioconjugation strategy based on activated alkynes is promising for the development of quick fluorescence labeling and functional modification of many targets and can be widely applied towards the fabrication of complex biomaterials and future in vivo labeling and detection.

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“…Tang and co-workers observed an unusual phenomenon on a class of molecules with propeller shape (e.g., tetraphenylethylene (TPE), siloles) which can turn on their fluorescence in the aggregate or solid states while keep non-emissive in diluted solutions. This phenomenon was termed as "aggregation-induced emission (AIE)" and the mechanism can be explained by a restriction of intramolecular motions (RIMs), including restriction of intramolecular vibrations (RIVs) and restriction of intramolecular rotations (RIR) [151][152][153][154][155][156][157][158][159]. Herein, AIE probes can overcome the drawbacks of the traditional fluorophore probes.…”

Section: Detection Of Mitochondrial Npsh Via a Snar Reaction Using Ether As A Leaving Groupmentioning

confidence: 99%

Fluorescent Probes for Live Cell Thiol Detection

2021

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Thiols play vital and irreplaceable roles in the biological system. Abnormality of thiol levels has been linked with various diseases and biological disorders. Thiols are known to distribute unevenly and change dynamically in the biological system. Methods that can determine thiols’ concentration and distribution in live cells are in high demand. In the last two decades, fluorescent probes have emerged as a powerful tool for achieving that goal for the simplicity, high sensitivity, and capability of visualizing the analytes in live cells in a non-invasive way. They also enable the determination of intracellular distribution and dynamitic movement of thiols in the intact native environments. This review focuses on some of the major strategies/mechanisms being used for detecting GSH, Cys/Hcy, and other thiols in live cells via fluorescent probes, and how they are applied at the cellular and subcellular levels. The sensing mechanisms (for GSH and Cys/Hcy) and bio-applications of the probes are illustrated followed by a summary of probes for selectively detecting cellular and subcellular thiols.

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Tetraphenylpyrazine-based luminogens with full-colour emission

Abstract: Full-colour emissive tetraphenylpyrazine-based luminogens are designed and prepared and their structure–photophysical property relationship is elaborated.

Cited by 50 publications

References 55 publications

Structural Modification Orientated Multifunctional AIE Fluorescence Probes: Organelles Imaging and Effective Photosensitizer for Photodynamic Therapy

Structural Modification Orientated Multifunctional AIE Fluorescence Probes: Organelles Imaging and Effective Photosensitizer for Photodynamic Therapy

A Simple Approach to Bioconjugation at Diverse Levels: Metal-Free Click Reactions of Activated Alkynes with Native Groups of Biotargets without Prefunctionalization

Fluorescent Probes for Live Cell Thiol Detection

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