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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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Polymer Chemistry · 2021 ·Vol. 12 ·期 48 ·7056-7064 · IF 5.582

Interlayer hydrogen bond-assisted poly(perylene diimide) photocatalysts to improve the oxygen evolution under visible light

Shufan Feng,Zhiqiang Wang,Huihui Xu,Sifan Li,Xueqing Gong,Jianli Hua

In recent years, polymeric photocatalysts have attracted worldwide attention due to their diverse synthetic approaches, tunable energy band and electronic structure. However, their photogenerated charge transfer is hindered by the lack of crystallinity, thus limiting their photocatalytic activity. In this work, four poly(perylene diimide) (poly(PDI)) photocatalysts (U-PDI, OA-PDI, MA-PDI and BU-PDI) with urea, oxalamide, malondiamide and biuret as the connecting groups were synthesized, respectively. Their photocatalytic oxygen production activity and charge transfer kinetics were investigated. It was found that BU-PDI exhibited the highest oxygen evolution rate (OER) of 46.80 μmol h−1 (2345 μmol g−1 h−1) under visible-light irradiation, which is 2.03 times higher than that of urea based U-PDI. The high OER of BU-PDI is mainly attributed to its interlayer hydrogen bond-enhanced crystallinity, which enhances the built-in electric field by avoiding dipole cancellation resulting by the disordered assembly and thus leads to an excellent charge transfer and separation capability. Moreover, to further expand its application in the utilization of solar energy, BU-PDI was used for the photodegradation of tetracycline and showed an excellent degradation rate and stability. This work may contribute to the development of photocatalysts for applications in photocatalytic water splitting and sewage treatment.

研究领域: 材料科学 · 环境科学
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CHINESE JOURNAL OF CATALYSIS · 2022 · IF 12.92

Hydrochloric acid-mediated synthesis of ZnFe2O4 small particle decorated one-dimensional Perylene Diimide S-scheme heterojunction with excellent photocatalytic ability

Yangrui Xu,Xiaodie Zhu,Huan Yan,Panpan Wang,Minshan Song,Changchang Ma,Ziran Chen,Jinyu Chu,Xinlin Liu,Ziyang Lu

The recyclable and stable ZnFe 2 O 4 small particle decorated one-dimensional perylene diimide (PDI) S-scheme heterojunction (1D PDI/ZnFe 2 O 4 ) is prepared by the hydrochloric acid-mediated (HCl-mediated) strategy, interestingly, the morphology of the 1D PDI/ZnFe 2 O 4 can also be effectively regulated by HCl-mediated process, the existence of HCl can regulate PDI into a uniform rod structure, while the co-existence of HCl and PDI can limit ZnFe 2 O 4 to become the uniform small particles. More importantly, based on the 1D rod structure of PDI and the small size effect of ZnFe 2 O 4 , carriers can migrate to the surface more easily, which can improve the photocatalytic activity. Meanwhile, due to the appropriate energy level structure, the S-scheme heterojunction structure is formed between PDI and ZnFe 2 O 4 , which eliminates meaningless photo-generated charge carriers through recombination and introduces strong redox to further enhance the photodegradation effect, thereby, 1D PDI/ZnFe 2 O 4 exhibits excellent photocatalytic ability, under the visible light irradiation, the degradation rate of tetracycline (TC) with 1D PDI/ZnFe 2 O 4 (66.67%) is 9.18 times that with PDI (7.26%) and 9.73 times that with ZnFe 2 O 4 (6.85%). This work proposes new ideas for the assembly of magnetic organic-inorganic S-scheme heterojunction photocatalysts.

研究领域: 材料科学 · 环境科学 · 化学
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CHEMOSPHERE · 2023 · IF 8.8

Perylene diimide/iron phthalocyanine Z-scheme heterojunction with strong interfacial charge transfer through π-π interaction: Efficient photocatalytic degradation of tetracycline hydrochloride

Kaiyang Shi,Man Zhou,Fulin Wang,Xiangwei Li,Weiya Huang,Kangqiang Lu,Kai Yang,Changlin Yu

The development of an all-organic Z-scheme heterojunction photocatalyst with the matched band structure, efficient electron transfer and excellent photocatalytic performance is valuable for a sustainable future. A novel perylene diimide/phthalocyanine iron (PDI/FePc) heterojunctions with strong π-π interaction were synthesized by a self-assembled method, which exhibited strong visible-light-driven photocatalytic degradation activities of tetracycline hydrochloride (TC). The TC removal rate over PDI/FePc was achieved three times and 87.5 times higher than that of PDI and FePc. PDI/FePc (131.1 mv·dec −1 ) presented a lower Taffel slope than that of PDI (228.6 mv·dec −1 ) for the oxidation. This may be due to the strong π-π interactions between PDI and FePc, which can reduce the layer spacing of the supramolecular structure and facilitate the separation and transfer of photogenerated carriers in the built-in electric field. In addition, radical quenching tests revealed that superoxide radicals (•O 2 − ) acted as a dominant role in photocatalytic oxidation. An increscent specific surface area of PDI decorated by FePc also gave the rapid pathway for charge transfer and enhanced the adsorption ability. This provides a new idea for the formation of heterojunction to improve the photocatalytic activity of organic supramolecular materials.

CAS / MDL: 107-95-9 60-54-8
研究领域: 材料科学 · 环境科学 · 有机化学
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Small · 2023 ·Vol. 19 ·期 39 ·2302665 · IF 13.3

Roles of Cobalt-Coordinated Polymeric Perylene Diimide in Hematite Photoanodes for Improved Water Oxidation

Lili Gao,Huan Chai,Huilin Niu,Jun Jin,Jiantai Ma

Interfacial charge recombination is a permanent issue that impedes the photon energy utilization in photoelectrochemical (PEC) water splitting. Herein, a conjugated polymer, urea linked perylene diimide polymer (PDI), is introduced to the designation of hematite-based composite photoanodes. On account of its unique molecule structure with abundant electronegative atoms, the O and N atoms with lone electron pairs can bond with Fe atoms at the surface of Zr 4+ doped α -Fe 2 O 3 (Zr:Fe 2 O 3 ) and thus establish charge transfer channels for expediting hole separation and migration. Meanwhile, PDI molecules can passivate the surface states in Zr:Fe 2 O 3 , which is in favor of suppressing carrier recombination. Particularly, Co 2+ is used to coordinate with PDI (Co-PDI) to accelerate hole extraction as well as utilization, and the as-obtained Co-PDI form type-II heterojunction with Zr:Fe 2 O 3 . Such a photoanode configuration takes advantage of the unique molecule structure of PDI, and the target Co-PDI/Zr:Fe 2 O 3 photoanodes eventually attain a photocurrent density of 2.17 mA cm −2 , which is inspirational for unearthing the potential use of conjugative molecules in PEC fields.

CAS / MDL: 10025-77-1 57-13-6
研究领域: 材料科学 · 光电化学
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SEPARATION AND PURIFICATION TECHNOLOGY · 2023 · IF 8.6

Covalent bond enhanced highly stable urea perylene diimide polymer for concurrent photocatalysis-persulfate activation

Qiuyi Ji,Pingping Lu,Shuying Li,Yuqi Lai,Jiandong Zhu,Zhe Xu,Gancheng Zuo,Yuan Ding,Shiyin Li,Shaogui Yang,Limin Zhang,Huan He

The self-assembled perylene diimide (SAPDI) connected by hydrogen bonds is limited by the instability of easy disintegration under alkaline conditions. The covalently linked urea PDI (UPDI) was synthesized under air conditions, and concurrent photocatalysis-persulfate activation (CPPA) system was constructed. A distinct synergistic effect was attained when UPDI/peroxymonosulfate (UPDI/PMS, 0.012 min −1 ) system was combined with photocatalysis (UPDI/PMS/Vis, 0.115 min −1 ) to degrade iohexol (IOX). The import of the light field can accelerate the electron migration between the electron donor and the acceptor with more reactive oxygen species (ROS) generation. Evidenced by quenching tests, electron paramagnetic resonance, the dominated reactive species in UPDI/PMS system tended to be holes and 1 O 2 . The utilization efficiency of ROS is crucial to improve the performance of CPPA. The stability of the UPDI system is superior to that of previously reported SAPDI and its derivatives or heterojunctions. The higher content of adsorbed oxygen can produce more reactive oxygen species (ROS), which is one of the reasons for the stable activity of UPDI in cyclic experiments. An enhancement for PMS activation on covalently bonded UPDI was observed based on density functional theory calculation. This study provides a new perspective for the application of stable and efficient metal-free water treatment technology.

CAS / MDL: 66108-95-0
研究领域: 环境科学 · 材料化学
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TALANTA · 2025 · IF 6.1

Ratiometric fluorescence aptasensor for lysozyme based on the controllable excimer formation of perylene probe

Juanmin Li,Shunsheng Zhao,Lihua Bai,Xiangrong Liu,Li Shang

As an important biological indicator, the abnormity of the lysozyme level is closely related to many diseases. Herein, we devise a novel ratiometric fluorescence aptasensor for lysozyme based on the controllable excimer formation of a perylene probe, N, N′-bis(6-caproic acid)-3,4:9,10-perylene diimide (PDI) induced by cationic silver nanoparticles (Ag NPs). Binding of lysozyme aptamer with multiple phosphate groups to cationic Ag NPs strongly hinders the formation of excimer, yielding intense monomer fluorescence of PDI probe. With the introduction of lysozyme, the adsorption of aptamer on the surface of Ag NPs will be weakened owing to the specific interactions between aptamer and lysozyme, which greatly facilitates the excimer formation of PDI. Based on the monomer-excimer transition triggered by lysozyme, ratiometric fluorescence aptasensor for lysozyme can be established. A good linear relationship between the ratio of monomer intensity to excimer intensity and the logarithm of lysozyme concentration was obtained in the range of 0.25–15 nM, and as few as 0.25 nM lysozyme could be easily detected. Moreover, excellent selectivity for lysozyme detection and satisfactory results in real sample analysis were also achieved. This work provides an innovative platform for the construction of simple, label-free ratiometric fluorescence sensors towards a wide range of analytes based on perylene probe.

研究领域: 生物化学 · 分析化学 · 医学诊断
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ANALYTICA CHIMICA ACTA · 2018 · IF 5.123

Tuning of the perylene probe excimer emission with silver nanoparticles

Juanmin Li,Huipeng Zhou,Yunyi Zhang,Sohail Anjum Shahzad,Meiding Yang,Zhenzhen Hu,Cong Yu

Silver nanoparticles (Ag NPs) enhanced perylene probe excimer emission is reported for the first time. It was observed that strong interactions between the perylene probe and the Ag NPs induced co-aggregation. As a result, a new in situ generated plasmonic absportion band of the Ag NPs at longer wavelength emerged. The monomer emission of the perylene probe was efficiently quenched, and dramatically enhanced probe excimer emission was observed. A remarkable emission enhancement of over 1000 fold was obtained compared to anionic polymers and other nanoparticles. The excimer emission intensity could be finely modulated by the size of the Ag NPs and the functionalities of the perylene probe. The observed Ag NPs enhanced perylene probe excimer emission shows good potential for the development of novel sensing techniques for various bioanalytical applications.

CAS / MDL: 78-10-4
研究领域: 化学 · 材料科学 · 生物分析
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APPLIED CATALYSIS B-ENVIRONMENTAL · 2018 · IF 11.698

Peroxymonosulfate-enhanced visible light photocatalytic degradation of bisphenol A by perylene imide-modified g-C3N4

Juanjuan Zhang,Xu Zhao,Yanbin Wang,Yan Gong,Di Cao,Meng Qiao

In this study, a metal-free photocatalyst (PI-g-C 3 N 4 ) was synthesized through an amidation reaction between perylene tetracarboxylic dianhydride (PTCDA) and graphitic carbon nitride (g-C 3 N 4 ). In order to enhance the photocatalytic degradation efficiency of bisphenol A (BPA) by 5 wt% PI-g-C 3 N 4 , peroxymonosulfate (PMS) was introduced into this system. When 5 mM PMS was added, 96% of BPA with an initial concentration of 10 mg/L was degraded within 60 min; the pseudo-first-order degradation kinetics constant of BPA was increased from 0.0057 to 0.0501 min −1 . Based on the photoelectrochemical analysis, it was proposed that PI-g-C 3 N 4 achieved a more effective separation of photogenerated electron–hole pairs and displayed higher conductivity than PTCDA and g-C 3 N 4 individually, thus promoting the PMS activation into active radicals by the photogenerated electrons. The BPA degradation was favored at high PMS concentrations under alkaline conditions. The slight inhibition effect of co-existing anions on the degradation of BPA followed the order: H 2 PO 4 − > NO 3 − ≈ HCO 3 − ; Cl − had a remarkable positive effect on the degradation of BPA. The radical quenching tests and electron spin resonance results indicated that O 2 − , 1 O 2 , and h + were the major species for the degradation of BPA. Combined with intermediates analysis, the degradation mechanism and pathway of BPA was proposed. The high stability of the 5 wt% PI-g-C 3 N 4 was finally demonstrated.

CAS / MDL: 299-11-6
研究领域: 环境科学 · 材料科学
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CHINESE JOURNAL OF CHEMISTRY · 2023 ·Vol. 41 ·期 11 ·1348-1354 · IF 5.4

Perylene Diimide Incorporated Polyurethane Polymer as Potential Colour Filter Material with Non-fluorescent Property†

Xin-Yi Zhang,Kai-Li Tian,Jie Liu,Wittaya Ngeontae,Ai-Juan Zhao,Maxim V. Bermeshev,Shi-Qing Wong,Kaspars Traskovskis,Zhijian Chen,Xiang-Kui Ren

Comprehensive Summary A novel polyurethane polymer containing perylene diimide (PDI) unit and aniline segment, denoted as PU-PDI, was designed and synthesized. Their tensile property and photophysical characteristic were investigated using various experimental and theoretical techniques. It is found that the elongation of PU-PDIs can reach more than 1000%, indicating good tensile performance. Moreover, based on the photoinduced electron transfer mechanism, the aniline segments in polyurethane can quench the auto-fluorescence of PDI unit to a negligible value, which overcomes the intractable fluorescence drawbacks of conventional colour filters. The non-emissive characteristic, in combination with the good thermal stability and tensile property of PU-PDI, provides a feasible design strategy to fabricate optical filters with high display quality.

CAS / MDL: 5124-30-1 822-06-0
研究领域: 材料科学 · 光学工程
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CHEMICAL ENGINEERING JOURNAL · 2023 · IF 15.1

Regulation of the band structure and water solubility of perylene imide derivatives based on bay-substitution to accelerate the transport of photogenerated carriers with TiO2

Yunning Chen,Zhengkai Wu,Renquan Guan,Xueying Cheng,Qingkun Shang,Yingnan Sun

Improving the efficiency of photogenerated charge separation and transport is the primary goal of designing and constructing efficient composite photocatalysts. The matching of energy bands and the formation of chemical bond between the two components are very conducive to the separation and transmission of photogenerated charges. Herein, three perylene diimide derivatives (PDIs) are synthesized by introducing sulfonic acid group (PDI-SA) and benzenesulfonic acid (PDI-BSA) respectively into the amide bond and further chlorine bay-substituting (Cl-PDI-BSA). The good water solubility of Cl-PDI-BSA ensures its forms a stable chemical bond with TiO 2 through the sulfonic acid group in the single molecular state, coupled with the matching of energy band structure, TiO 2 @Cl-PDI-BSA exhibited excellent performance upon visible light photocatalytic degradation to phenol and trenbolone acetate (TBA). It can remove 100% of phenol in 15 min and 100% trenbolone acetate (TBA) in 30 min, which is 14.3 times that of TiO 2 . Combining to DFT calculation, Kelvin probe force microscope and EPR analysis prove that bay chlorine substitution has a greater impact on the energy band structure and electron cloud distribution of PDIs than N-sulfonation, thereby seriously affecting the transport of photogenerated carriers with TiO 2 .

研究领域: 材料科学 · 环境科学 · 化学
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JOURNAL OF COLLOID AND INTERFACE SCIENCE · 2021 · IF 8.128

Hierarchical self-assemblies of carnosine asymmetrically functioned perylene diimide with high optoelectronic response

Tian Tian,Duo Wei,Lingling Ge,Zhifeng Wang,Chong Chen,Rong Guo

Hypothesis: Taking advantage of photoinduced electron transfer , one dimensional organic nanomaterials with tunable donor-acceptor (D-A) interface provide a promising avenue to get high optoelectric properties. However, strong charge transfer interaction between D and A segments impedes the formation of long-range ordered structure, which limits the charge transport through efficient π electronic delocalization. Incorporation of chiral peptide offering various hydrogen bonding (H-bonding) along with asymmetric molecular structure enables substantially controllable D-A interface and tunable organization of the π -conjugates. Experiments: A new amphiphilic perylene diimide (CUPDI) with PDI as an acceptor is designed and synthesized. A polar chiral dipeptide composed of β -alanine and l -histidine with the imidazole ring as the donor i.e. , l -carnosine, is incorporated at one of imides . Transition of various supramolecular assemblies of CUPDI is realized by changing CUPDI concentration and solvents. The photoelectronic properties of the assemblies are investigated as well as their association with the microstructure of the nanomaterials. Findings: Delicately tuned hydrogen bonds between the peptides and π - π interaction between PDI cores in different solvents enable the formation of assemblies with multifarious microstructures such as small spherical aggregates, nanowires with uniform diameter, nanobelts , and irregular aggregates. The maximum amount of photocurrent enhancement is up to 1.08 µA observed for the nanobelt, four times higher than that of irregular aggregates. However, the nanowires show the best performance of 7.1-fold in response to ammonia. Thus, the photoelectric performances are strongly dependent on the the molecular arrangement within the nanomaterials.

研究领域: 有机化学 · 材料科学 · 纳米技术 · 光电学
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