Review on application of perylene diimide (PDI)-based materials in environment: Pollutant detection and degradation

Zhou, Wenwu; Le, Guo; Zhang, Nana; Ji, Qiuyi; Xiang, Weiming; He, Huan; Xu, Zhe; Qi, Chengdu; Li, Shiyin; Yang, Shaogui; Xu, Chenmin

doi:10.1016/j.scitotenv.2021.146483

Cited by 57 publications

(54 citation statements)

References 352 publications

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“…Since perylene derivatives have strong fluorescence emission and high photostability, these hydrosoluble PMIs could be useful as fluorescent probes for cell and organelle imaging, as well as fluorescent tools for environmental and biological analysis. 41 , 42 …”

Section: Resultsmentioning

confidence: 99%

Hydrosoluble Perylene Monoimide-Based Telomerase Inhibitors with Diminished Cytotoxicity

et al. 2022

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Telomerase is essential for the immortality characteristics of most cancers. Telomerase-specific inhibitors should render cancer cells to replicative senescence without acute cytotoxicity. Perylene-based G-quadruplex (G4) ligands are widely studied as telomerase inhibitors. Most reported perylene-based G4 ligands are perylene diimides (PDIs), which often suffer from self-aggregation in aqueous solutions. Previously, we found that PM2, a perylene monoimide (PMI), exhibited better solubility, G4 binding affinity, and telomerase inhibition than PIPER, the prototypic PDI. However, the acute cytotoxicity of PM2 was about 20–30 times more than PIPER in cancer cells. In this report, we replaced the piperazine side chain of PM2 with ethylenediamine to yield PM3 and replaced the N , N -diethylethylenediamine side chain of PM2 with the 1-(2-aminoethyl) piperidine to yield PM5. We found that asymmetric PMIs with two basic side chains (PM2, PM3, and PM5) performed better than PIPER (the prototypic PDI), in terms of hydrosolubility, G4 binding, in vitro telomerase inhibition, and suppression of human telomerase reverse transcriptase ( hTERT ) expression and telomerase activity in A549 cells. However, PM5 was 7–10 times less toxic than PM2 and PM3 in three cancer cell lines. We conclude that replacing the N , N -diethylethylenediamine side chain with the 2-aminoethylpiperidine on PMIs reduces the cytotoxicity in cancer cells without impacting G4 binding and telomerase inhibition. This study paves the way for synthesizing new PMIs with drug-like properties for selective telomerase inhibition.

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Section: Resultsmentioning

confidence: 99%

Hydrosoluble Perylene Monoimide-Based Telomerase Inhibitors with Diminished Cytotoxicity

et al. 2022

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“…The red-colored perylenediimides are widely used as high-grade industrial paints in the plastic, automobile, and fiber industries . Their synthesis by Langhal’s method involves the use of high-boiling NMP as the solvent and a mixture of substrates perylene-3,4,9,10-tetracarboxylic dianhydride (PTCDA) and amines (in large excess) heated at high temperatures (>160 °C) for 24 h for better conversions. , Other imide-based dyes, naphthalic imides (NIs)s are also vastly used chromophores.…”

Section: Mechanochemical Synthesis Of Conventional Dyesmentioning

confidence: 99%

“…In a recent study, Ahmed and co-workers reported a mechanochemical synthesis of photochromic tetrahydroindolizines (THIs) and studied the substituent effect on their photochromic properties. 38 Five THIs (32) were prepared by grinding a mixture of spirocyclopropenes ( 29) and 1-substituted aryl-3,4-dihydroisoquinolines (30) in a mortar and pestle with silica gel (2 g per mmol of 29) as the grinding matrix. A 40 min period of grinding followed by a 2 h rest period, further 40 min of grinding, and standing for 8 h afforded the products dialkyl 5′,6′dihydro-10′b-substituted-1′H-spiro[fluorine-9,1′-pyrrolo[2,1a]isoquinoline-2′,3′-dicarboxylate (32) in 64−87% yields (Scheme 8).…”

Section: Mechanosynthesis Of Miscellaneous Dyesmentioning

confidence: 99%

Mechanochemical Synthesis of Organic Dyes and Fluorophores

et al. 2021

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The syntheses of dyes and fluorophores have significant commercial importance. In recent years, mechanochemistry has emerged as a green and sustainable alternative for the synthesis of conventional dyes, new fluorophores, and also synthetic modification of known dyes for their use as chemosensors. The dyestuffs based on BODIPYs, rhodamine, fluorescein, perylenedimides, coumarins, benzothiazoles, etc. were synthesized or derivatized by grinding or milling. The synopsis aims to pay key attention to their synthesis and the applications as chemosensors will be briefly covered.

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“…perylene (See Figure 3). [217][218][219] Figure 3. Chemical structure of perylene and perylene diimide and the various possible chemical modifications of the perylene core.…”

Section: Temporal Control High Polymerization Speed Spatial Controlmentioning

confidence: 99%

Recent advances on perylene-based photoinitiators of polymerization

Dumur

2021

European Polymer Journal

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Photopolymerization is an active research field requiring the design of new photosensitizers enabling to convert more efficiently liquid monomers as solids. Especially, a great deal of efforts is devoted to reduce the polymerization time, improve the monomer conversion while using safer irradiation conditions. To reach these goals, choice of the photosensitizers is crucial as it constitutes the unique element of the photocurable resins capable to interact with light. In this field, perylene which is a pigment of polycyclic aromatic structure has been studied as soon as 1978 for the design of photoinitiating systems. Since these pioneering works, a wide range of perylene-based photoinitiators have been developed, ranging from organic photocatalysts to water-soluble photoinitiators. In this review, an overview of the different perylene-based photoinitiators reported to date is provided. To evidence the efficiency of these structures, comparisons which benchmark photoinitiators is provided.

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Review on application of perylene diimide (PDI)-based materials in environment: Pollutant detection and degradation

Cited by 57 publications

References 352 publications

Hydrosoluble Perylene Monoimide-Based Telomerase Inhibitors with Diminished Cytotoxicity

Hydrosoluble Perylene Monoimide-Based Telomerase Inhibitors with Diminished Cytotoxicity

Mechanochemical Synthesis of Organic Dyes and Fluorophores

Recent advances on perylene-based photoinitiators of polymerization

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