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PDI衍生物
ANALYTICAL CHEMISTRY · 2023 · IF 7.4

Nanoassemblies Based on a Cationic Perylene Diimide Derivative and Sodium Dodecyl Sulfate: A Simple Fluorescent Platform for Efficient Analysis of Aflatoxin B1

Yijian Zhao,Tianyue Liu,Jinghui Gao,Qiaojuan Zhang,Mengyu Liao,He Cheng,Jingsheng Tian,Zhiyi Yao

Aflatoxin B1 (AFB1) is a kind of potently carcinogenic fungal metabolite in food threatening human health, and it is crucial and challenging to develop advanced nonimmune approaches for AFB1 determination. Addressing this challenge, we successfully constructed a nanoassembly (PdE-PDI/SDS) by noncovalently coupling a cationic perylene diimide derivative (PdE-PDI) and sodium dodecyl sulfate (SDS), exhibiting high-density charges and a specific surface area for rapid sensing of AFB1. The large electronic conjugate structure and rigid plane of PdE-PDI enable it to form more stable σ–π, π–π coordination, and hydrogen bonds with AFB1. Additionally, the introduction of SDS significantly amplifies noncovalent interactions and enhances the quenching efficiency of PdE-PDI toward AFB1. The proposed PdE-PDI/SDS exhibited excellent specificity to AFB1 and showed dosage-sensitive detection with detection limit as low as 0.74 ng mL–1. Finally, the PdE-PDI/SDS was successfully applied in cereal samples with good recoveries from 94.61 to 109.92%. To our knowledge, this is the first time a fluorescent strategy from the point of self-assembly for AFB1 determination is reported, which holds great promise for wide applications of perylene diimide derivative in food safety.

研究领域: 食品安全 · 分析化学 · 纳米技术
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MICROCHEMICAL JOURNAL · 2023 · IF 4.8

Smartphones and paper-assisted detection of TNP using a cationic perylene diimide derivative in 100% aqueous media

Meiyi Liu,Weilian Zheng,Yi Yang,Ge Shi,Yining Li,Shuai Zhou,Yijian Zhao,Zhiyi Yao

2,4,6-trinitrophenol (TNP) is an environmentally deleterious substance with high toxicity and explosibility. It is of great significance for environmental protection and public health to establish a rapidly on-site monitoring method for perilous TNP. Current methods for detecting TNP mainly rely on traditional laboratory analysis lacking rapid detection through intelligent modes. Herein, we construct a smartphone recognition based fluorescence sensing system via the supramolecular assembly of a perylene probe to quantify TNP. The sensing platform consists of a fluorescent probe based on quaternary ammonium functionalized perylene (PDI-BTMA), as the TNP-response recognition element, and smartphones as optical signals receptors bringing simpleness, celerity, and portability for TNP monitoring. The sensor reveals dual output signals of color and fluorescence in response to TNP. The results show that the optical responses of PDI-BTMA can be attributed to the formation of the supramolecular complex (PDI-BTMA/TNP) via non-covalent interactions including static electricity, hydrophobic interaction, charge transfer, and π-π stacking. It shows a wide linear range for TNP of 200–1200 nM with a detection limit of 9 nM. In addition, we successfully made portable PDI-BTMA fluorescence paper. The RGB value of fluorescence color was also collected by using the smartphone-assisted sensing platform, and the G/B channel values show a linear relationship with TNP concentration in 0.1–50 μM, with the lowest detection concentration of 48.4 nM. Additionally, it could be successfully utilized for quantitative TNP monitoring in environmental water and soil samples, which achieved a greater recovery rate in the range of 99–110%. This research integrating the PDI-BTMA probe with a smartphone firstly presents a new strategy for real-time and on-site monitoring of TNP in the environment.

研究领域: 环境科学 · 分析化学
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LANGMUIR · 2024 · IF 3.7

Self-Assembly of Amphiphilic PDI and NDI Derivatives with Opposite Thermoresponsive Fluorescent Behaviors in Aqueous Solution

Bizhuo Wei,Huajing Li,Huan Chu,Huanhuan Dong,Yijun Zhang,Cai-Li Sun,Yuangang Li

This work presents a study of the thermally induced aggregation of perylene diimide (PDI) and naphthalene diimide (NDI) derivatives modified with oligo ethylene glycol (OEG) chains in aqueous solution. Water-soluble and flexible OEG side chains were introduced into the π-core of glutamate-modified NDI and PDI structures, and the aggregation process was modulated by heating or cooling in water. Interestingly, a rare opposite temperature response of fluorescent behavior from the two amphiphilic chromophores was revealed, in which the PDI exhibited fluorescent enhancement, while fluorescent quenching upon temperature increase was observed from the NDI assembly. The mechanism of thermally induced aggregation is clearly explained by studies with various spectroscopic techniques including UV–visible, fluorescence, 1H NMR, 2D NMR spectroscopy, and SEM observation as well as control experiments operated in DMSO solution. It is found that although similar J-aggregates were formed by both amphiphilic chromophores in aqueous solution, the temperature response of the aggregates to temperature was opposite. The degree of PDI aggregation decreased, while that of NDI increased upon temperature rising. This research paves a valuable way for understanding the complicated supramolecular behaviors of amphiphilic chromophores.

CAS / MDL: 288-32-4 128-69-8
研究领域: 超分子化学 · 材料科学 · 物理化学
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CHEMISTRY-A EUROPEAN JOURNAL · 2024 · IF 3.9

S/Se-Annulated Star-Shaped Perylene Diimides (PDIs) with Large Two-Photon Absorption (TPA) Cross-Section in NIR-I Region

Dandan Li,Wenrong Zhao,Gang Li,Yan Xu,Liang Xu,Bo Tang

Graphical Two novel star-shaped fluorophores named PDI−S and PDI−Se are constructed by S/Se-fused perylene diimides (PDIs) connected with bicarbazole core. Particularly, PDI−S presents excellent two-photon absorption cross-action (δ TPA ) of 3775 GM excited with 800 nm light, which is the highest value based on PDIs motif in the NIR−I region (700–900 nm). Two-photon absorption (TPA) has attracted growing attention over recent years owing to the wide range of applications in organic nonlinear optical (NLO) materials. The quantitative sensitivity of a two-photon molecular entity is determined by its TPA cross-section (δ TPA ). Perylene diimides (PDIs) are excellent n-type organic semiconductor materials demonstrating distinguished thermal, optical, and chemical stability. Nonetheless, PDIs-based scaffolds exhibit poor δ TPA in the NIR−I region (700–900 nm) due to the lack of suitable molecular design. Here, two novel star-shaped PDIs fluorophores, namely PDI−S and PDI−Se, were constructed by four periphery S/Se-fused PDIs connected with bicarbazole core. PDI−S manifested excellent δ TPA of 3775 GM, which are among the highest values reported for PDIs excited in the NIR−I region.

研究领域: 有机化学 · 材料科学
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Asian Journal of Organic Chemistry · 2020 ·Vol. 9 ·期 7 ·1076-1080 · IF 3.13

Nucleophilic Substitution Reaction of Pentafluorophenyl Aminated Perylene Diimide system with N,N-Dimethylformamide

Siyu Wu,Gengwen Yin,Caihong Cheng,Bo Liang,Haiquan Zhang

Graphical A new product -PDMBPRI-4F was synthesized by one-step method, which has the special property of fluorescence quenching caused by intramolecular charge transfer. Nucleophilic substitution process with loss of one fluorine atom was observed when pentafluorophenyl substituted benzo[ghi]perylene triimide and perylene diimide were heated in N , N -dimethylformamide, in which N , N -dimethylformamide acted both as solvent and nucleophile reagent. Unexpectedly, the obtained product exhibited significant intramolecular charge transfer optical properties in solutions. The mechanism of nucleophilic substitution and the influence of substituent were further studied and proposed in this manuscript.

研究领域: 有机化学 · 材料科学
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