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ChemistrySelect · 2022 ·Vol. 7 ·期 46 ·e202203635 · IF 2.307

Rapid and Visual Detection of Al3+ Based on Supramolecular Self-Assembly of a Water-Soluble Perylene Diimide Derivative

Mei Shi,Jinghan Jiang,Xiao Gao,Yining Li,Keren Xiao,Qi-an Han,Weifu Kong,Qingliang Liu,Zhiyi Yao

Graphical A water-soluble PDI, N, N′ -bis (L-phenylalanine)-3,4,9,10-perylene tetracarboxylic diimide (PDI-Phe) is designed and synthesized for rapid and selective fluorescent detection of Al 3+ in aqueous solution. In the presence of Al 3+ , non-covalent interactions such as electrostatic and π-π interactions would promote supramolecular self-assembly between PDI-Phe and Al 3+ , making the aggregation and fluorescence quenching of PDI-Phe, thereby realizing the quantitative detection of Al3+ between 100 nM and 900 nM. The limit of detection (LOD) of Al 3+ was as low as 6.54 nM. Aluminum (Al) is widely used in food industry, but excessive absorption of Al 3+ causes many serious health problems. Therefore, it is of great significance to determine the specificity of Al 3+ . In this study, we designed and synthesized a water-soluble perylene diimide derivative (PDI-Phe) for monitoring Al 3+ rapidly and visually. Through absorption and emission spectroscopy techniques, we systematically explored the properties and mechanism of the sensor to Al 3+ . The limit of detection (LOD) of Al 3+ was as low as 6.54 nM. And with the existence of Al 3+ , electrostatic interaction and intermolecular π-π stacking promoted the aggregation and fluorescence quenching of PDI-Phe. Even in the presence of other analytes, PDI-Phe still had excellent selectivity and sensitivity for Al 3+ detection. Besides, it also had the characteristics of low cost, good water solubility, excellent chemical and optical stability, and easy synthesis. Finally, this method can be further applied to tap water samples.

研究领域: 分析化学 · 材料科学 · 环境科学
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JOURNAL OF COLLOID AND INTERFACE SCIENCE · 2022 · IF 9.965

Morphology engineering and photothermal effect derived from perylene diimide based derivative for boosting photocatalytic hydrogen evolution of ZnIn2S4

Lin Liu,Yan Wu,Ru Song,Yu Zhang,Yafei Ma,Jun Wan,Meili Zhang,Huali Cui,Hua Yang,Xiaoli Chen,Jijiang Wang

The construction of excellent photocatalysts for splitting water into hydrogen is highly desirable to realize carbon neutralization. In this work, an innovative and well-designed S-scheme photocatalyst composed of ultrathin ZnIn 2 S 4 (ZIS) nanosheets uniformly anchored on the surface of organic semiconductor PDIIM is successfully fabricated. Within the heterojunction , perylene diimide with an imidazole group (PDIIM) is strategically applied as a structure template, which plays a crucial role in optimizing the morphology, increasing the active sites of sulfur vacancies , providing the additional photothermal effect, and promoting photogenerated charge separation of the catalyst. The photocatalytic H 2 generation rate of the ZIS/PDIIM heterojunction with an optimized mass ratio reaches up to 13.04 mmol/g/h, which is 2.64 times and 14.02 times higher than that of pristine ZIS and PDIIM, respectively. The outstanding photocatalytic activity is attributed to the synergistic effect of the above advantages. Importantly, the photothermal effect induced by PDIIM belonging to the perylene diimide-based derivative was discovered to accelerate photocatalytic H 2 generation for the first time. This work provides valuable insight into the utilization of perylene diimide-based derivatives in the construction of multi-effect enhancement photocatalysts and their application in photothermal-assisted photocatalytic hydrogen evolution .

研究领域: 材料科学 · 能源科学
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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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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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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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DYES AND PIGMENTS · 2016 · IF 4.055

Novel hydrogen bonding composite based on copper phthalocyanine/perylene diimide derivatives p-n heterojunction with improved photocatalytic activity

Hailong Wang,Lele Zhao,Xueqiang Liu,Jing Xu,Wenlong Hou,Jianmin Wang,Enfang He,Ruijun Zhang,Haiquan Zhang

Among photocatalytic materials, p-n heterojunction-type photocatalysts has good photocatalytic performance under visible light irradiation. Herein, a novel Copper phthalocyanine/perylene diimide derivatives p-n heterojunction photoeatalysts based on the intermolecular hydrogen bond between pyridyl and carboxyl was designed and characterized using FT-IR, UV–vis and photoluminescence spectra, and then compared their photocatalytic performance by degradation for rhodamine B (RhB) under visible light irradiation. The hydrogen bond composites shows significant higher photocatalytic activity comparing with its parent, and the photocatalysis increased with increasing of mole fraction of perylene diimide derivatives. The change of morphology and p-n heterojunction structure are in favor of the high photocatalytic active. Furthermore, the photocatalytic mechanism was investigated by radical scavengers testing, that confirmed hydroxyl radical ( OH) was the main reactive species for the degradation of RhB.

研究领域: 材料科学 · 环境科学 · 化学
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CHEMICAL ENGINEERING JOURNAL · 2024 · IF 13.3

Regulating the photoelectric effect and built-in electric field based on the electronic and spatial effects of substituents on PDIs amide sites to enhance the photocatalytic performance of PDIs

Zhengkai Wu,Yunning Chen,Xueying Cheng,Renquan Guan,Shuyu Chen,Yingna Guo,Qingkun Shang

How to design and optimize the single-molecule structure of perylene diimide derivatives (PDIs) to obtain high-performance photocatalysts is one of the challenges facing the current research field of PDIs photocatalysis. In this article, we regulate the π-π self-assembly stacking and optoelectronic properties of PDIs by changing the type and position of substituents on the amide site. The PDI-PBA photocatalyst with excellent performance was obtained from seven types of PDIs supramolecular materials. Theoretical calculations and optoelectronic performance tests have shown that PDI-PBA has good crystallinity and maximum dipole moment, resulting in its maximum built-in electric field, effectively promoting the separation and transport of photo-generated carriers. The transient absorption spectra further indicate that photogenerated electrons and holes of PDI-PBA have outstanding separation efficiency and ultra-long lifetime. In the batch reactor, PDI-PBA can degrade almost 100% acetaminophen within 60 min. In the dynamic cycling system with a surface hydraulic load of 14.56 L/(m 2 ·h), the efficiency of PDI-PBA photocatalytic degradation of acetaminophen can reach 84%. PDI-PBA can also effectively degrade phenol, levofloxacin, and ciprofloxacin. This work provides a successful example for the design of novel and efficient PDIs supramolecular materials, and lays the foundation for the application of PDIs photocatalysts in practical wastewater treatment.

研究领域: 材料科学 · 环境科学 · 化学
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LUMINESCENCE · 2021 ·Vol. 37 ·期 2 ·247-254 · IF 2.464

Synthesis, luminescence, and excited-state absorption properties of disubstituted perylene diimide derivatives modified at bay region

Qian Cheng,Zhiyuan Chen,Qing Zhang,Senqiang Zhu,Rui Liu,Hongjun Zhu

Three A–π–A or D–π–D perylene diimide ( PDI ) derivatives with varied groups on π-conjugate were synthesized and characterized. The photophysical properties of these compounds were systematically studied by spectral experiments and density functional theory calculations. All compounds displayed intense absorption bands at 300–800 nm wavelengths. However, diverse groups on the π-conjugate influenced the UV–vis absorption. Electron-withdrawing groups on PDI-2 caused a slight red shift at the 350–400 nm wavelength and a blue shift after 400 nm wavelength. At the same time, the electron-donating substituents on PDI-3 caused an obvious red shift of this band. These PDI derivatives exhibited emission in solution at room temperature (λ em = 500–850 nm). The quantum yield of PDI-3 decreased, while the electron-donating substituents were introduced to the π-conjugated motifs. However, the quantum yield of PDI-2 increased when electron-withdrawing substituents were introduced to the π-conjugated motifs. In addition, PDI-1 and PDI-2 exhibited broad triplet transient absorption in the visible region. These photophysical properties could help us to understand the relationship between structure and photophysical properties of perylene diimide derivatives and exploit more original perylene diimide-based optical functional materials.

研究领域: 材料化学 · 光物理学
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ANALYTICAL AND BIOANALYTICAL CHEMISTRY · 2023 ·Vol. 415 ·期 23 ·5845-5854 · IF 4.3

Effect of perylene assembly shapes on photoelectrochemical properties and ultrasensitive biosensing behaviors toward dopamine

Chi Kuan-Neng,Liu Jia-Wen,Guan Yan,Li Qiu-Xia,Yang Tong,Hu Rong,Yang Yun-Hui

In this study, a photoelectrochemical (PEC) sensor based on perylene diimide derivatives (PDIs) was developed for the ultrasensitive quantification of dopamine (DA). PDIs were able to form self-assembled semiconductor nanostructures by strong π-π stacking, suitable for photoactive substances. Moreover, the shape of the PDI significantly affected the PEC properties of these nanostructures. The results showed that amino PDI with two-dimensional (2D) wrinkled layered nanostructures exhibited superior PEC properties relative to one-dimensional (1D) nanorods and fiber-based nanostructures (methyl and carboxyl PDIs). Based on these results, a mechanism for PEC sensor action was then proposed. The presence of 2D amino-PDI resulted in accelerated charge separation and transport. Furthermore, dopamine acted as effective electron donor to cause an increase in photocurrent. The as-obtained sensor was then used to detect small molecules like DA. A blue light optimized sensor at an applied potential of 0.7 V showed a detection limit of 1.67 nM with a wide linear range of 5 nM to 10 μM. On the other hand, the sensor presented acceptable reliability in determining DA in real samples. A recovery rate between 97.99 and 101.0% was obtained. Overall, controlling the morphology of semiconductors can influence PEC performance, which is a useful finding for the future development of PEC sensors. Graphical Abstract

CAS / MDL: 109-76-2 128-69-8
研究领域: 分析化学 · 生物传感 · 材料科学
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Frontiers in Chemistry · 2020 · IF 3.693

Propeller-Like All-Fused Perylene Diimide Based Electron Acceptors With Chalcogen Linkage for Efficient Polymer Solar Cells

Li Ying,Gong Yufei,Che Yongjie,Xu Xiaopeng,Yu Liyang,Peng Qiang

Perylene diimide (PDI) is a widely explored chromophore for constructing non-fullerene acceptors (NFAs) for polymer solar cells (PSCs). The advantage of using PDI derivatives lies in the readily availability of PDI unit which largely reduces the synthesis cost and improves material stability. Indeed, the recent development of high performance NFAs shed light on the feasibility of the commercialization, but the complex synthesis and poor stability of the top performing NFAs cast a shadow on this bright future. Our previous work has demonstrated a propeller-like structure with three PDIs lined to a benzene center core with a C-C bond which prevented the PDIs to aggregate into undesired large crystals. In this work, we designed and synthesized three new propeller-like PDI derivatives with extra chalcogen linkages between the PDIs and the center core to form all-fused rigid structures. These molecules showed more suitable absorption range than that of their unfused counterparts when blend with donor polymer PTB7-Th. Comparing between the molecules with extra oxygen, sulfur or selenium linkages, the sulfur-based BTT-PDI outperformed the others due to its higher photon absorption and charge transport abilities. This work demonstrated the great potential of PDI derivatives for PSC applications and explored the influences of linkage type on the fused PDI derivatives, which provided a useful tuning knob for molecular design of PDI-based NFAs in the future.

研究领域: 材料科学 · 有机化学
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SOLAR ENERGY · 2020 · IF 4.608

Effects of solvent additives on the morphology and transport property of a perylene diimide dimer film in perovskite solar cells for improved performance

Tengling Ye,Shan Jin,Ranbir Singh,Manish Kumar,Wenbo Chen,Daizhe Wang,Xiaoru Zhang,Wenxu Li,Dongqing He

Perylene diimide derivatives (PDIs) are a kind of very promising non-fullerene electron transport material for organic-inorganic perovskite solar cells (PerSCs), owing to their excellent photoelectric properties and low-cost synthesis. However, their tendency to form aggregates strongly influences the film morphology and transport properties. Herein, we provided a simple way to tune the morphology and transport properties of PDIs by solvent additive engineering. A series of solvent additives (1,8-diiodooctane, 1-chloronaphthalene, 1-phenylnaphthalene, 1-methylnaphthalene) was investigated for their role in the morphology and transport property of PDI dimer (Bis-PDI-T-EG) film as well as on the photovoltaic performance of PerSCs . Among these four solvent additives, 1-methylnaphthalene (MN) was found one of the best additive that possesses good adjusting ability to control both morphological and electrical properties of Bis-PDI-T-EG film. The fabricated PerSCs with optimized Bis-PDI-T-EG + 0.05 v/v% MN electron transport layer (ETL) displayed the best power conversion efficiency (PCE) of 14.96%. The performance of PerSCs was further improved by adding 0.05 wt% graphene together with 0.05 v/v% MN, and the maximum PCE of 15.11% was achieved.

研究领域: 材料科学 · 能源科学 · 光电化学
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SENSORS AND ACTUATORS B-CHEMICAL · 2016 · IF 4.758

High performance hydrazine vapor sensor based on redox mechanism of twisted perylene diimide derivative with lower reduction potential

Jianmin Wang,Enfang He,Xueqiang Liu,Lan Yu,Hailong Wang,Ruijin Zhang,Haiquan Zhang

A conductometric film device prepared using solution processing method based on a perylene diimide derivative with low reduction potentials (E 1/2 (PDI/PDI· − )   =   −0.098   V and E 1/2 (PDI· − /PDI 2− )   =   −0.360   V) for detection of hydrazine (NH 2 NH 2 ) vapors under ambient conditions is reported. The film device exhibited highly selectivity, reproducibility and ultrafast response towards hydrazine vapor with liner concentration-dependent characteristic under hydrazine vapor. However, the film device is unstable under high concentration (800   ppm) of hydrazine, which ascribed to the change of the film morphology demonstrated by SEM images combined with UV–vis spectra before and after exposed to 800   ppm hydrazine vapors. In addition, the effect of the film thick, the working voltages, relative humidity and temperature on the sensing performance were also discussed. Furthermore, the sensing mechanism of the film device to hydrazine vapor was investigated by UV–vis spectra, spectroelectrochemistry and cyclic voltammetry, which indicated that the redox of d-THBPDI plays a critical role in the sensing process.

研究领域: 材料科学 · 化学传感器 · 电化学
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