A perylene diimide-based fluorescent probe for the selective detection of hypochlorite in living cells

Zhang, Le; Zhang, Yifan; Han, Ying‐Feng

doi:10.1039/d2qm00283c

“…Thus, PDIs have been recognized as one of the extensively studied artificial building blocks in supramolecular chemistry, including chemosensing [2,30]. Given the fact that pH control is usually critical for the optimized aggregation behavior and shape-defined assembly morphology of PDIs molecules, as well as their uses for ion sensing in the liquid phase [3,31,32], PDI−based fluorescent sensors have demonstrated great potential for use in pH probing or detection of pH-related ions [3,16,17].…”

Section: Ph Sensing Based On Supramolecular (De)aggregation Mechanismmentioning

confidence: 99%

Architectures and Mechanisms of Perylene Diimide-Based Optical Chemosensors for pH Probing

Chen

¹

,

Zhang

²

,

Zhu

³

et al. 2023

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The precise control and monitoring of pH values remain critical for many chemical, physiological and biological processes. Perylene diimide (PDI)-based molecules and materials exhibit excellent thermal, chemical and photochemical stability, unique UV-vis absorption and fluorescent emission properties, low cytotoxicity, as well as intrinsic electron-withdrawing (n-type semiconductor) nature and impressive molecular assembly capability. These features combined enable promising applications of PDIs in chemosensors via optical signal modulations (e.g., fluorescent or colorimetric). One of the typical applications lies in the probing of pH under various conditions, which in turn helps monitor the extracellular (environmental) and intracellular pH change and pH-relying molecular recognition of inorganic or organic ions, as well as biological species, and so on. In this review, we give a special overview of the recent progress in PDI-based optical chemosensors for pH probing in various aqueous and binary water–organic media. Specific emphasis will be given to the key design roles of sensing materials regarding the architectures and the corresponding sensing mechanisms for a sensitive and selective pH response. The molecular design of PDIs and structural optimization of their assemblies in order to be suitable for sensing various pH ranges as applied in diverse scenarios will be discussed in detail. Moreover, the future perspective will be discussed, focusing on the current key challenges of PDI-based chemosensors in pH monitoring and the potential approach of new research, which may help address the challenges.

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Alkyl‐Doping Enables Significant Suppression of Conformational Relaxation and Intermolecular Nonradiative Decay for Improved Near‐Infrared Fluorescence Imaging

Liang,

Pan,

Chen

et al. 2024

Angewandte Chemie

0

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Despite various efforts to optimize the near‐infrared (NIR) performance of perylene diimide (PDI) derivatives for bio‐imaging, convenient and efficient strategies to amplify the fluorescence of PDI derivatives in biological environment and the intrinsic mechanism studies are still lacking. Herein, we propose an alkyl‐doping strategy to amplify the fluorescence of PDI derivative‐based nanoparticles for improved NIR fluorescence imaging. The developed PDI derivative, OPE‐PDI, shows much brighter in n‐Hexane (HE) compared with that in other organic media, and the excited state dynamics investigation experimentally elucidates the solvent effect‐induced suppression of intermolecular energy transfer and intramolecular nonradiative decay as the underlying mechanism for the fluorescence improvement. Theoretical calculations reveal the lowest reorganization energies of OPE‐PDI in HE among various solvents, indicating the effectively suppressed conformational relaxation to support the strongest radiative decay. Inspired by this, an alkyl atmosphere mimicking HE is constructed by incorporating the octadecane into OPE‐PDI‐based nanoparticles, permitting up to 3‐fold fluorescence improvement compared with the counterpart nanoparticles. Owing to the merits of high brightness, anti‐photobleaching, and low biotoxicity for the optimal nanoparticles, they have been employed for probing and long‐term monitoring of tumor. This work highlights a facile strategy for the fluorescence enhancement of PDI derivative‐based nanoparticles.

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Alkyl‐Doping Enables Significant Suppression of Conformational Relaxation and Intermolecular Nonradiative Decay for Improved Near‐Infrared Fluorescence Imaging

Liang,

Pan,

Chen

et al. 2024

Angew Chem Int Ed

0

View full text Add to dashboard Cite

Despite various efforts to optimize the near‐infrared (NIR) performance of perylene diimide (PDI) derivatives for bio‐imaging, convenient and efficient strategies to amplify the fluorescence of PDI derivatives in biological environment and the intrinsic mechanism studies are still lacking. Herein, we propose an alkyl‐doping strategy to amplify the fluorescence of PDI derivative‐based nanoparticles for improved NIR fluorescence imaging. The developed PDI derivative, OPE‐PDI, shows much brighter in n‐Hexane (HE) compared with that in other organic media, and the excited state dynamics investigation experimentally elucidates the solvent effect‐induced suppression of intermolecular energy transfer and intramolecular nonradiative decay as the underlying mechanism for the fluorescence improvement. Theoretical calculations reveal the lowest reorganization energies of OPE‐PDI in HE among various solvents, indicating the effectively suppressed conformational relaxation to support the strongest radiative decay. Inspired by this, an alkyl atmosphere mimicking HE is constructed by incorporating the octadecane into OPE‐PDI‐based nanoparticles, permitting up to 3‐fold fluorescence improvement compared with the counterpart nanoparticles. Owing to the merits of high brightness, anti‐photobleaching, and low biotoxicity for the optimal nanoparticles, they have been employed for probing and long‐term monitoring of tumor. This work highlights a facile strategy for the fluorescence enhancement of PDI derivative‐based nanoparticles.

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A perylene diimide-based fluorescent probe for the selective detection of hypochlorite in living cells

Abstract: Electron leak in the respiratory chain of mitochondria is the major causative factor for the production of reactive oxygen species (ROS), including hypochlorite (OCl-). As one of the most important...

Cited by 10 publications

References 72 publications

Architectures and Mechanisms of Perylene Diimide-Based Optical Chemosensors for pH Probing

Architectures and Mechanisms of Perylene Diimide-Based Optical Chemosensors for pH Probing

Alkyl‐Doping Enables Significant Suppression of Conformational Relaxation and Intermolecular Nonradiative Decay for Improved Near‐Infrared Fluorescence Imaging

Alkyl‐Doping Enables Significant Suppression of Conformational Relaxation and Intermolecular Nonradiative Decay for Improved Near‐Infrared Fluorescence Imaging

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