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perylenediimide
Materials Express · 2019 ·Vol. 9 ·期 7 ·741-748 · IF 1.465

An ultrasensitive photoelectrochemistry sensor for ascorbic acid based on etching perylenediimide modified CoOOH nanosheets

Chi Kuan-Neng,Hu Rong,Yang Yun-Hui

In this work, a neoteric photoelectrochemistry (PEC) sensor on account of perylenediimide (PDI) by coupling with ascorbic acid (AA) responsive decomposition of cobalt oxyhydroxide (CoOOH) nanosheets was developed. PDI is a kind of organic photoelectric material with strong photoelectrochemical properties in aqueous solution. When the surface of the PDI is modified by CoOOH, the photoelectric properties of the PDI could be effectively decreased. However, when AA is present, CoOOH is reduced to Co2+ while the photoelectric properties of PDI are restored. The photoelectric sensor constructed thereby exhibits high selectivity and transient response, and is simple in operation, low in cost and short in time, and provides a novel detection method for small molecule ascorbic acid. In the case of a signal-to-noise ratio of 3, the detection limit is 33.4 nM. This paper opens a new PEC method to detection of AA.

研究领域: 分析化学 · 生物传感 · 材料科学
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COMPOSITES PART B-ENGINEERING · 2024 · IF 12.7

Synergy of interfacial reinforcing and damage monitoring at elevated temperature by constructing fluorescence interphase of perylenediimide nanowires in carbon fiber/bismaleimide composites

Yuhang Sun,Qingfu Su,Gang Li,Xiaoping Yang,Xiaobiao Zuo

Amino-terminated perylenediimide (PDI) was designed and used to construct molecular assembly interphase with high temperature resistance and fluorescence on modified carbon fiber (CF-PDI) surface, and the correlations of the novel interphase with interfacial reinforcement and damage monitoring of carbon fiber/bismaleimide (CF/BMI) composites after treatment at 25 °C, 100 °C, 200 °C and 250 °C were investigated. Reticular nanowire structures from PDI self-assembly were observed on CF-PDI surface, leading to the increase of chemical activity and roughness of fiber surface. The partial detachment and decreased surface activity of the nanowire structures of PDI assembly on CF-PDI surface appeared with increasing the temperature, resulting from the weakening of π-π stacking and sectional breakage of intermolecular hydrogen bonding at high temperature. Compared with CF-desized composites, transverse fiber bundle tensile strength and interfacial shear strength were increased by 76.6 % and 52.2 % after treatment at 250 °C, which was ascribed to the enhanced interfacial bonding between PDI nanowires and BMI matrix. The confocal laser scanning microscope images and grayscale color maps showed the strong green fluorescence on CF-PDI surface and its composites at 25 °C, while the fluorescence intensity was gradually decreased with the increase of temperature. The fluorescence disappearance of damage region after low-velocity impact damage was observed after treatment at 200 °C and 250 °C, which realized damage monitoring at high temperature in CF/BMI composites.

CAS / MDL: 373-44-4 128-69-8
研究领域: 材料科学 · 复合材料工程
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PHYSICAL CHEMISTRY CHEMICAL PHYSICS · 2017 ·Vol. 19 ·期 35 ·23898-23904 · IF 4.123

Langmuir–Blodgett films of perylene bisimide derivatives and fluorescent recognition of diamines

Congdi Shang,Li Wang,Yanqin An,Ping Chen,Xingmao Chang,Yanyu Qi,Rui Kang,Yu Fang

Fast, sensitive and selective detection of diamines in the vapor phase is of pivotal importance for air and food quality monitoring. In this work, an electron-poor fluorophore, perylene bisimide (PBI), was modified with hydrophilic residues at its bay positions, resulting in an amphiphilic derivative, PEBBO. Photophysical studies revealed that the compound shows a strong aggregation tendency in various solvents, but the aggregates could be highly fluorescent provided suitable solvents are used. Accordingly, a fluorescent film was constructed via utilization of the well-known Langmuir–Blodgett technique. Sensing performance studies revealed that the film as prepared is sensitive and selective to the presence of diamines in air. Specifically, (1) the experimental detection limit is lower than 0.016 g m−3 and the linear range of the analysis extends from 0.33 g m−3 to 8.20 g m−3 when ethylenediamine was adopted as an example analyte; (2) the presence of other amines and solvents shows little effect upon detection; (3) the response time is less than 5 s. Considering the importance of diamine sensing, the convenience of fluorescence techniques and the superiorities of the film and method as developed, it is believed that the present work is of great importance for promoting technical progress in diamine sensing.

研究领域: 化学 · 环境科学 · 材料科学
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Journal of Materials Chemistry B · 2020 ·Vol. 8 ·期 16 ·3661-3666 · IF 5.344

Novel perylene probe-encapsulated metal–organic framework nanocomposites for ratiometric fluorescence detection of ATP

Xiaomeng Zhou,Juanmin Li,Li-Li Tan,Qiang Li,Li Shang

Adenosine triphosphate (ATP) plays an important role in various biological processes and the ATP level is closely associated with many diseases. Herein, a novel ratiometric fluorescence assay for ATP was developed based on the excimer-monomer transfer of a perylene probe. By encapsulating a perylene probe, N,N′-bis(6-caproic acid)-3,4:9,10-perylenediimide (PDI), into zeolitic imidazolate framework-8 (ZIF-8) nanocrystals, fluorescent nanocomposites (PDI@ZIF-8) with significant excimer emission of the perylene probe were prepared for the first time. The presence of ATP will trigger the decomposition of PDI@ZIF-8 due to much stronger coordination between ATP and Zn2+ than that of 2-methylimidazole and Zn2+. As a result, the encapsulated PDI probes were released, leading to significantly increased monomer emission accompanying the decrease in the excimer emission. The excimer-monomer transition signal was utilized for ratiometric ATP sensing and its potential application for detecting ATP in cell lysates was also successfully demonstrated.

研究领域: 生物化学 · 分析化学 · 材料科学
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Polymer Chemistry · 2019 ·Vol. 10 ·期 20 ·2551-2558 · IF 4.76

A perylenediimide-based nanocarrier monitors curcumin release with an “off–on” fluorescence switch

Wenyu Cheng,Hongtao Chen,Chendong Ji,Ru Yang,Meizhen Yin

Perylenediimide-cored (PDI-cored) polymers have been widely applied as fluorescent drug carriers due to their high fluorescence quantum yield and outstanding chemical/photophysical stability. However, most of these delivery systems lack detailed drug delivery specifics, especially when and where the drug is released. In this study, a PDI-based nanocarrier (PPL-B) is constructed and applied to monitor curcumin release with an “off–on” fluorescence switch. The star-shaped drug carrier has an amphiphilic structure with fluorescent PDI as the core and poly(amino acid) as the shell, which is suitable for drug delivery. A model drug curcumin is loaded to PPL-B and quenches its fluorescence significantly through photo-induced electron transfer (PET). Upon curcumin release, the fluorescence of PPL-B achieves an “off–on” switch as a result of PET interruption. In light of this, curcumin release is successfully monitored by CUR@PPL-B at the cellular level. This PDI-based nanocarrier for drug release monitoring with a PET mechanism shows great potential in the drug delivery field.

研究领域: 药学 · 材料科学 · 生物医学工程 · 纳米技术
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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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CHEMISTRY-A EUROPEAN JOURNAL · 2024 · IF 3.9

A Three-Dimensional Non-Fullerene Acceptor with Contorted Hexabenzocoronene and Perylenediimide for Organic Solar Cells

Xin Zhu,Lei Yang,Yangyang Pan,Yuqin Yang,Xuming Ding,Chuanming Wan,Zhuo Zhang,Yun Luo,Qinghai Zhou,Liwei Wang,Shengxiong Xiao

Graphical A conjugated molecular HBC-4-PDI with three-dimensional geometry is synthesized and applied as a non-fullerene acceptor material in the active layer of organic solar cells. Although fullerene derivatives such as [6,6]-phenyl-C 61 /C 71 -butyric acid methyl ester (PC 61 BM/PC 71 BM) have dominated the the photoactive acceptor materials in bulk heterojunction organic solar cells (OSCs) for decades, they have several drawbacks such as weak absorption, limited structural tunability, prone to aggregation, and high costs of production. Constructing non-fullerene small molecules with three-dimensional (3D) molecular geometry is one of the strategies to replace fullerenes in OSCs. In this study, a 3D molecule, contorted hexa- cata -hexabenzocoronene tetra perylenediimide (HBC-4-PDI), was designed and synthesized. HBC-4-PDI shows a wide and strong light absorption in the whole UV-vis region as well as suitable energy levels as an acceptor for OSCs. More importantly, the 3D construction effectively reduced the self-aggregation of c -HBC, leading to an appropriate scale phase separation of the blend film morphology in OSCs. A preliminary power conversion efficiency of 2.70 % with a champion open-circuit voltage of 1.06 V was obtained in OSCs with HBC-4-PDI as the acceptor, which was the highest among the previously reported OSCs based on c -HBC derivatives. The results indicated that HBC-4-PDI may serve as a good non-fullerene acceptor for OSCs.

研究领域: 材料科学 · 能源科学 · 有机光电
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ANALYTICAL SCIENCES · 2022 ·Vol. 38 ·期 7 ·989-1002 · IF 1.967

Preparation and evaluation of a perylenediimide bridged bis(β-cyclodextrin) chiral stationary phase for HPLC

Zeng Qingli,Zhong Hui,Zhang Tianci,Huang Zhiqin,Li Laisheng

A large π-conjugated perylenediimide bridged bis (β-cyclodextrin)-bonded stationary phase (PBCDP) was first prepared and characterized. The chiral HPLC performance was systematically evaluated using a series of chiral probes. The results showed that PBCDP could resolve 36 kinds of chiral compounds in reversed-phase and polar organic modes with high resolutions ( R s) 1.48–3.28 for profens, 1.25–2.85 for triazoles, 1.34–5.29 for flavanones, 1.66–4.58 for amino acids and 1.22–1.97 for β-blockers. Especially, PBCDP could completely resolve acidic non-steroidal chiral drugs (profens) and simultaneously resolve basic five triazole pesticides, which were difficult to separate by ordinary CDCSP. Compared with CDCSP (15 kinds), the new stationary phase has a wider resolution range (36 kinds). Obviously, the synergistic inclusion of the two cavities of bridged cyclodextrin, as well as the large π–π stacking, hydrogen bond, dipole–dipole and basic primary amine site (–NH–) provided by the perylenediimide bridging group contributed together to the improvement of the above chiral separations. PBCDP was a new type of versatile chiral separation material without port derivatization. Graphical abstract

研究领域: 分析化学 · 色谱技术
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LUMINESCENCE · 2022 ·Vol. 37 ·期 10 ·1741-1750 · IF 2.613

Amino-functionalized perylenediimide derivative with dual fluorescence emission for the detection of ascorbic acid in vivo and in vitro

Gui-Qun Zhang,Kuan-Neng Chi,Chao Yao,Tong Yang,Rui-Lin Zhang,Rong Hu,Yun-Hui Yang

The rapid, sensitive, and selective detection of ascorbic acid (AA) is of significance in medical assays and diagnostics. In this work, a new aminoperylenediimide (APDI) derived ratiometric fluorescent probe based on the specific redox reaction of cobalt oxyhydroxide (CoOOH) and AA was constructed. APDI exhibited dual fluorescence emission peaks at 549 and 596 nm with an excitation wavelength of 494 nm. In the presence of CoOOH, the dual fluorescence could be quenched. The dominant fluorescence quenching mechanism was caused by the inner filter effect. Using the red emission as a reference, the fluorescence intensity ratio ( F 549 / F 596 ) was linearly correlated with the concentration of AA over a range of 0.05 to 1 μM. The limit of detection for AA was found to be 17 nM. Importantly, the probe was successfully used to detect AA in living cells. Therefore, this high sensitivity and selectivity strategy could directly survey the AA levels in real samples.

研究领域: 分析化学 · 生物医学工程 · 荧光光谱
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