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Polymers · 2021 ·Vol. 13 ·期 11 ·1755 · IF 4.329

Recyclable Shape-Memory Waterborne Polyurethane Films Based on Perylene Bisimide Modified Polycaprolactone Diol

Kang Wei,Haitao Zhang,Jianbo Qu,Jianyong Wang,Yang Bai,Futao Sai

Currently, much attention is given to the functionality and recyclability of waterborne polyurethane (WPU). Herein, ε-caprolactone was used as a chain extender for grafting onto perylene bisimide (PBI) and 1,4-butanediol (BDO) via ring-opening reactions to obtain PBI-PCL and BDO- PCL. Then, two kinds of WPU, namely PBI-WPU (PWPU) and BDO-WPU (BWPU), were fabricated using PBI-PCL/polytetrahydrofuran ether glycol (PTMG) and BDO-PCL/PTMG, respectively, as mixed soft segments. The properties and appearance of PWPU and BWPU emulsions were analyzed in terms of particle size, zeta potential and TEM images, and the results showed that PWPU emulsions had uniform particle size distribution and decent storage stability. AFM and DMA results revealed that PWPU films possessed a more significant degree of microphase separation and a higher glass transition temperature (Tg) than BWPU films. The PWPU films displayed good shape-memory and mechanical properties, with tensile strength up to 58.25 MPa and elongation at break up to 1241.36%. TGA analysis indicated that PWPU films had better thermal stability than BWPU films. More importantly, the PWPU films could be dissolved in a mixed solvent of acetone/ethanol (v/v= 2:1) at room temperature. The dissolved PWPU could be dispersed in deionized water to prepare waterborne polyurethane again. After the recycling process was repeated three times, the recycled PWPU emulsion still exhibited good storage stability. The recycled PWPU films maintained their original thermal and mechanical properties. Comparing the properties of BWPU and PWPU showed that the soft segment structure had important influence on waterborne polyurethane performance. Therefore, PWPU may have great potential applications in making recycling and shape-memory coating or paint.Keywords:perylene bisimide;waterborne polyurethane;polycaprolactone diol;recyclable;shape-memory

CAS / MDL: 64-17-5 872-50-4 67-64-1
研究领域: 材料科学 · 化学工程
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SENSORS AND ACTUATORS B-CHEMICAL · 2018 · IF 5.667

Methylene blue sensitized photoelectrochemical biosensor with 3,4,9,10-Perylene tetracarboxylic acid film as photoelectric material for highly sensitive Pb2+ detection

Liaojing Huang,Liu Yang,ChuanChao Zhu,Hanmei Deng,Guangpeng Liu,Yali Yuan

It is of great significance to explore reliable and sensitive methods for the trace detection of lead ions (Pb 2+ ), which may cause serious adverse effect to human health. Herein, we proposed a methylene blue (MB) sensitized signal-on photoelectrochemical (PEC) biosensor with 3,4,9,10-perylene tetracarboxylic acid (PTCA) film as photoelectric material for highly sensitive Pb 2+ detection. First, PTCA was modified on the electrode surface, manifesting wonderful film-forming property and acquiring a satisfactory initial PEC signal. Afterward, Pb 2+ -dependent DNAzyme modified on electrode was cleaved by target Pb 2+ , followed by hybridizing MB assembled 3D DNA networks with the exposed Pb 2+ catalytic strand. Significantly, in the presence of sensitizer MB, the PEC signal of PTCA was extraordinarily increased and the designed biosensor performed a high sensitivity with a detection limit down to 0.03 pM. Therefore, with enzyme-free assembly of MB embedded 3D DNA networks, this dye-sensitized strategy exhibited effective and uncomplicated amplification technology for Pb 2+ detection.

CAS / MDL: 7220-79-3 61-73-4
研究领域: 分析化学 · 环境科学 · 生物传感技术
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ACS Applied Materials & Interfaces · 2019 · IF 8.456

Perylene Diimide and Luminol as Potential-Resolved Electrochemiluminescence Nanoprobes for Dual Targets Immunoassay at Low Potential

Yue Song,Wei Zhang,Shuijian He,Lei Shang,Rongna Ma,Liping Jia,Huaisheng Wang

In the field of clinical diagnosis, it is important to construct a potential-resolved multiplex electrochemiluminescence (ECL) biosensor for decreasing the false-positive rate and improving the diagnostic accuracy. However, the shortage of low-potential cathodic luminophores between −1 and 0 V (vs Ag/AgCl) severely limited the development of the biosensor. Herein, we synthesized a novel luminophore N,N-bis-(3-dimethyl aminopropyl)-3,4,9,10-perylene tetracarboxylic acid diimide (PDI), which gave dual emissions at −0.25/–0.26 V with K2S2O8 as a co-reactant in aqueous solution. The ECL was assigned to excited J-type PDI dimers. Then, PDI and luminol were used as luminophores to respectively combine with graphite oxide and gold nanoparticles and form potential-resolved ECL nanoprobes. Also, this potential-resolved ECL nanoprobes were respectively functionalized by secondary antibodies (Ab2) to construct a low-potential sandwiched ECL immunosensor for tumor markers carcinoembryonic antigen (CEA) and α-fetoprotein (AFP) simultaneous determination during linear scanning potential range from −0.6 to 0.6 V. The prepared multiplex immunosensor exhibited sensitive ECL response for CEA at −0.6 V due to PDI and that for AFP at 0.6 V due to luminol, and both linear semilogarithmical ranges were from 0.1 pg to 1 ng mL–1. In addition, PDI with dual ECL peaks showed enticing prospect of built-in self-calibration for a precise quantitative and bioimaging analysis.

CAS / MDL: 69-93-2
研究领域: 生物医学工程 · 分析化学 · 临床诊断
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ACS Applied Materials & Interfaces · 2021 · IF 9.229

Rechargeable Mg-Ion Full Battery System with High Capacity and High Rate

Zishuai Zhang,Yi Li,Gongyuan Zhao,Lin Zhu,Ye Sun,Flemming Besenbacher,Miao Yu

Thanks to the low cost, free dendritic hazards, and high volumetric capacity, magnesium (Mg)-ion batteries have attracted increasing attention as alternative energy storage devices to lithium-ion batteries. Despite the successful development of electrode materials, the real-life application potential of Mg-ion full battery systems (MIFBSs) is largely hindered by the lack of suitable electrode couples and hence low diffusion kinetics, which induce low specific capacity, poor rate performance, and low working voltage. Herein, we report an aqueous rechargeable MIFBS by employing copper hexacyanoferrate (CuHCF) as the cathode and 3,4,9,10-perylene-tetracarboxylic acid diimide (PTCDI) as the anode in 1 moL L–1 MgCl2 electrolyte. The combination of PTCDI//CuHCF allows efficient redox and convenient intercalation/deintercalation of Mg2+ at the electrodes while facilitating a fast transfer of Mg2+ between the two electrodes. As a result, the system delivers a high capacity of ∼120.3 mAh g–1 at a current density of 0.5 A g–1 after 200 operation cycles with a broadened voltage range (0–1.95 V) and maintains a capacity of ∼97.8 mAh g–1 at 2.0 A g–1 after 1000 cycles. Even at a high current density of 5.0 A g–1, the battery provides a steady capacity of ∼81.4 mAh g–1 over 5000 cycles. Moreover, after being applied at 11.0 A g–1, the system can deliver a capacity of ∼126.5 mAh g–1 at 0.5 A g–1. This work emphasizes the great promise of developing suitable electrode couples for aqueous MIFBSs to achieve high capacity and high rate.

研究领域: 材料科学 · 电化学
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IONICS · 2021 ·Vol. 27 ·期 11 ·4907-4916 · IF 2.817

A fluorescent probe for selective detection of Fe3+ by using a self-assembled nitrogen-doped carbon quantum dots-3,4,9,10-perylenetetracarboxylic acid composite

Wang Kunjie,Chen Jinliang,Li Hongxia,Zhang Mengmeng,Liao Quanxing,Wang Letong,Zhang Yuhua,Niu Xiaohui

We have synthesized nitrogen-doped carbon quantum dots (N-CQDs) via one-step hydrothermal method by using citric acid and urea as carbon sources, In order to solve the agglomeration effect of carbon quantum dots and increase its recognition sites, and then combined the N-CQDs with 3,4,9,10-perylenetetracarboxylic acid (PTCA) to synthesize an self-assembled carbon quantum dots-3,4,9,10-perylenetetracarboxylic acid (N-CQDs/PTCA) composite, which has strong fluorescent properties. The fluorescence spectrum showed that the prepared self-assembled composite (N-CQDs/PTCA) has strong yellow-green light emission near 510 nm. The characterizations such as ultraviolet–visible absorption, X-ray electron spectroscopy, Fourier infrared spectroscopy, and transmission electron microscopy have confirmed that the N-CQDs and PTCA were combined together successfully. And the prepared self-assembled N-CQDs/PTCA was independent of excitation. It has stable and strong fluorescence properties and can be used as a fluorescent probe. The study also found that in the presence of Fe 3+ ions, the fluorescence of self-assembled carbon quantum dots N-CQDs/PTCA will be quenched, and the quenching efficiency had a good linear relationship with the concentration of Fe 3+ ions. Therefore, we proposed to use the self-assembled carbon quantum dots N-CQDs/PTCA as a fluorescent probe to detect Fe 3+ selectively. The results showed that the method was fast, reliable, obvious detection signal, selective, and not affected by incubation time. The detection limit is 0.041 μM, which provides a new idea for the detection of Fe 3+ ions by using self-assembled method and has broad application prospects. Graphical abstract

研究领域: 化学 · 材料科学 · 分析化学
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TETRAHEDRON · 2023 · IF 2.1

Photoinduced nucleophilic substitution reaction of 1,7-dibromo-perylene diimide to form 1-bromo-7-hydroxyl perylene diimide

Jianping Zhang,Jinming Liu,Gengwen Yin,Wenlong Hou,Haiquan Zhang

Nucleophilic substitution reaction of 1,7-dibromo-perylene diimide derivatives can expend the chemical structure and photophysical properties of perylene diimide. Here, we reported firstly the synthesis and mechanism of 1-bromo-7-hydroxyl perylene diimide derivative by the 1,7-dibromo-perylene diimide derivative in electron donor solvents (such as, NMP, DMF and etc) and under visible light irradiation . The structure of 1-dibromo-7-hydroxyl perylene diimide was confirmed by HR-MS, UV–Vis absorption spectra and comparison of UV–Vis absorption spectra with product from the heating chemical reaction. Furthermore, the 1-bromo-7-hydroxyl-perylene diimide derivative showed a higher optical response to some metal ions , such as Fe 3+ , Cu 2+ and etc.

研究领域: 有机化学 · 光化学 · 材料科学
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JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY · 2023 · IF 4.3

Rapid detection of glutathione and spermidine by an in-situ pre-modification method based on perylene diimide derivatives

Keren Xiao,He Cheng,Yumeng Chen,Luting Ren,Qiaojuan Zhang,Qimeng Wang,Nan Cheng,Wenjing Hong,Zhiyi Yao

For some small biomolecules with simple structures, it is difficult to achieve rapid detection because they lack strong interactions with probes. To solve this problem, we have developed an approach based on perylene diimide derivatives combining an in-situ pre-modification technique. In this strategy, the nucleophilic reaction of o-phthalaldehyde (OPA) was used to enhance the non-covalent interactions between the analyte and probe. This method was utilized for sensing glutathione (GSH) and spermidine (SPD) and had the characteristics of fast response, wide detection range, and high selectivity. Moreover, it has been validated with real samples and the detection mechanism was investigated systematically. To the best of our knowledge, this is the first attempt to apply perylene diimide derivatives to the detection of some biological small molecules by an in-situ pre-modification method.

研究领域: 分析化学 · 生物化学
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Solar RRL · 2020 ·Vol. 5 ·期 2 ·2000453 · IF 7.527

Controlled Synthesis of Higher Interfacial Electron Transfer Graphite-Like Carbon Nitride/Perylenetetracarboxylic Diimide Heterogeneous for Enhanced Photocatalytic Activity

Hong Miao,Jun Yang,Yuqiang Sheng,Wenlu Li,Yongfa Zhu

To exploit the noble-metal-free, highly efficient and broad-spectrum responsive photocatalyst of perylenetetracarboxylic diimide (PDI), a self-assembled PDI nanowire is loaded on the surface of a graphite-like carbon nitride (g-C 3 N 4 ) nanosheet and forms an all-organic supramolecular 1D/2D heterogeneous g-C 3 N 4 /PDI with broad-spectrum responsiveness (254–700 nm), which can improve the absorption efficiency of solar energy. In the g-C 3 N 4 /PDI system, the π–π conjugated bond in the g-C 3 N 4 /PDI can accelerate the photoinduced charge carrier transfer. On the other hand, the interlaced band structure between the g-C 3 N 4 and PDI and the Z-scheme pathway of the carriers leads to the spatial separation of redox reaction sites. Therefore, the g-C 3 N 4 /PDI photocatalyst reaches strong redox ability in the photocatalytic process. In detail, the photocatalytic phenol degradation of g-C 3 N 4 /PDI (0.837 h −1 ) is enhanced 2.67 and 9.19 times higher as the pure PDI and g-C 3 N 4 , respectively, under the full spectra. Meanwhile, the H 2 evolution activity of the g-C 3 N 4 /PDI (1649.93 μmol g −1 h −1 ) is 2.03 times higher than g-C 3 N 4 nanosheet (814.03 μmol g −1 h −1 ).

研究领域: 材料科学 · 光催化化学
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Molecular Catalysis · 2024 · IF 3.9

Synthesis of bay-substituted perylene diimide as bifunctional photocatalyst for enhanced water oxidation and hydrogen peroxide generation

Bo Zhang,Shoufeng Wang,Shihao Min,Kang Li,Longtian Kang,Wenlie Lin

Rational design of semiconductor molecule structure is of significant importance for achieving the multifunctional photocatalysis. Herein, three end/bay-substituted perylenediimide (PDI) molecules, including bis(N-carboxymethyl) perylenediimide (H 2 PDI), 1,7-dibromo-substituted H 2 PDI (2Br-H 2 PDI) and 1,6,7,12-tetraether-substituted H 2 PDI (4CH 3 CH 2 O-H 2 PDI), are synthesized for photocatalytic oxygen evolution (POE) and oxygen reduction reaction (ORR). One-dimensional H 2 PDI nanorods, two-dimensional 2Br-H 2 PDI nanosheets, and zero-dimensional 4CH 3 CH 2 O-H 2 PDI nanoparticles are obtained. Under visible light, 4CH 3 CH 2 O-H 2 PDI as photocatalyst (5.31 mmol·g −1 ·h −1 ) exhibits the 1.8-times and 20-times POE rate of 2Br-H 2 PDI (2.93 mmol·g −1 ·h −1 ) and H 2 PDI (0.26 mmol·g −1 ·h −1 ) with AgNO 3 as sacrificial agent. Additionally, the POE rate can be further improved to 9.34 mmol·g −1 ·h −1 with the Co 2+ doping of 4CH 3 CH 2 O-H 2 PDI. With isopropanol as sacrificial agent, the H 2 O 2 evolution rate of 657.4 μM·g −1 ·h −1 can be also achieved via photocatalytic ORR with 4CH 3 CH 2 O-H 2 PDI as catalyst, which is ∼3 and ∼4 times those of 2Br-H 2 PDI (220.8 μM·g −1 ·h −1 ) and H 2 PDI (160.0 μM·g −1 ·h −1 ), respectively. Especially, in the O 2 - or air- saturated aqueous solution without sacrificial agent, the H 2 O 2 rate of 273.1 or 112.7 μM·g −1 ·h −1 can be also achieved. This work provides a promising way to design the PDI-based multifunctional photocatalysts.

研究领域: 材料化学 · 光催化 · 能源化学
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MOLECULES · 2024 ·Vol. 29 ·期 17 ·4196 · IF 4.2

Novel PDI-NH/PDI-COOH Supramolecular Junction for Enhanced Visible-Light Photocatalytic Phenol Degradation

Yongzhang Xu,Xingrui Luo,Fulin Wang,Wentao Xiang,Chensheng Zhou,Weiya Huang,Kangqiang Lu,Shaoyu Li,Man Zhou,Kai Yang

The development of efficient and environmentally friendly photocatalysts is crucial for addressing global energy and environmental challenges. Perylene diimide, an organic supramolecular material, holds great potential for applications in mineralized phenol. In this study, through the integration of different mass ratios of unmodified perylenimide (PDI-NH) into the self-assembly of amino acid-substituted perylenimide (PDI-COOH), a novel supramolecular organic heterojunction (PDICOOH/PDINH) was fabricated. The ensuing investigation focuses on its visible-light mineralized phenol properties. The results show that the optimal performance is observed with a composite mass fraction of 10%, leading to complete mineralization of 5 mg/L phenol within 5 h. The reaction exhibits one-stage kinetics with rate constants 13.80 and 1.30 times higher than those of PDI-NH and PDI-COOH, respectively. SEM and TEM reveal a heterogeneous interface between PDI-NH and PDI-COOH. Photoelectrochemical and Kelvin probe characterization confirm the generation of a built-in electric field at the interface, which is 1.73 times stronger than that of PDI-COOH. The introduction of PDI-NH promotes π-π stacking of PDI-COOH, while the built-in electric field facilitates efficient charge transfer at the interface, thereby enhancing phenol decomposition. The finding demonstrates that supramolecular heterojunctions have great potential as highly effective photocatalysts for environmental remediation applications.

CAS / MDL: 107-95-9 64-17-5
研究领域: 环境科学 · 材料科学
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Chemistry-An Asian Journal · 2018 ·Vol. 13 ·期 14 ·1784-1790 · IF 3.692

Solvents Effects on Film Morphologies and Memory Behavior of a Perylenediimide-Containing Pendent Polymer

Ming Wang,Qi-jian Zhang,Zhuang Li,Hua Li,Jian-Mei Lu

Graphical Remember this? A sandwich-structured device of indium tin oxide (ITO)/polymer/aluminum exhibited different electrical behavior and threshold voltages in different solvent mixtures of different ratios (see figure). This study suggests that polymeric memory behavior can be efficiently adjusted through the use of mixed solvents. The large polydispersity index of functional pendant polymers has hindered their application in semiconductors. Herein, a novel pendant polymer with perylenediimide (PDI) in the side chains was successfully synthesized through ring-opening metathesis polymerization (ROMP) with a very low polydispersity index. The synthesized polymers were spin-coated on indium tin oxide (ITO) substrate by using a mixture of 1,2-dichlorobenzene ( o -DCB) and methanol (MeOH) solvents. The surface morphologies and intermolecular π–π stacking of the fabricated film could be adjusted through tuning of the ratio of o -DCB and MeOH, and thus, the sandwich-structured device of ITO/polymer/aluminum exhibited different electrical behavior. The threshold voltages of the devices decreased as the MeOH content was increased from 0 to 30 % (v/v); however, the device changed from being unrewritable to rewritable if the MeOH content was increased to 40 %; a probable mechanism for this process is discussed. It is hoped that this new idea of synthesizing narrow polydispersity index pendant polymers, and the fabrication of high-quality films through the use of a mixture of solvents could allow high-performance memory devices to be prepared in the future.

CAS / MDL: 4048-33-3 56-12-2
研究领域: 材料科学 · 电子工程
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APPLIED SURFACE SCIENCE · 2019 · IF 5.155

Perylene diimide derivative regulate the antimony sulfide morphology and electrochemical sensing for hydrazine

Yongshun Gao,Shuo Zhang,Wenlong Hou,Huiyun Guo,Qizhe Li,Danyang Dong,Siyu Wu,Shiyuan Zhao,Haiquan Zhang

Sb 2 S 3 /perylene diimide derivatives composite micro-spheres composed of slight dendrites were synthesized by solvothermal reaction. Perylene diimide derivative with two carboxyl groups at amine position as morphology-controlling reagent is the key factor for determining the microscopic morphology of Sb 2 S 3 in this system. Time-dependent experiments have been conducted to track the formation of Sb 2 S 3 micro-spheres. Moreover, the composite material showed an excellent sensitivity of 29.8 μA mM −1  cm 2 with a low detection limit of 50 pM, it also showed better stability and selectivity in hydrazine detection. This approach not only regulate the morphology and composition of Sb 2 S 3 submicron materials effectively, but also provide new ideas for the manufacture of metal sulfide- perylenediimide amino acid derivative materials, which will be suitable for sensing, catalysis, and photovoltaic applications.

研究领域: 材料科学 · 电化学 · 分析化学
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