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Photoinduced excimer generation in perylene diimide dimer:effects of solvent polarity[Invited]

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Chinese Optics Letters 2022年第10期20卷 49-54页

作者：冉光柳汪航宋宇菁刘亚辉薄志山张文凯 Department of Physics and Applied Optics Beijing Area Major Laboratory Center for Advanced Quantum StudiesBeijing Normal UniversityBeijing 100875China College of Textiles&Clothing Qingdao UniversityQingdao 266071China Beijing Key Laboratory of Energy Conversion and Storage Materials College of ChemistryBeijing Normal UniversityBeijing 100875China

The aggregation and photoinduced excited state dynamics of organic π-conjugated molecules play a vital role in solar energy conversion and applications.This work investigates how solvent polarity affects the aggregation behavior and the photophysical process of perylene diimide dimer(PDI-II).The results show that the conjugations between PDI intramolecular chromophores are more likely to generate excimer,and the conjugations between PDI intermolecular chromophores are more likely to experience symmetry-breaking charge separation.Our study can provide a reference for the design of high-efficiency solar energy conversion materials.

关键词： excimer perylene diimide dimer solvent effect transient absorption spectroscopy

Interface Engineering of Inverted Perovskite Solar Cells Using a Self-doped perylene diimide Ionene Terpolymer as a Thickness-Independent Cathode Interlayer

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Chinese Journal of Chemistry 2023年第23期41卷 3326-3332页

作者： Daizhe Wang Tengling Ye Dongqing He Xiaochen Sun Yong Zhang Department of Applied Chemistry School of Chemistry and Chemical EngineeringHarbin Institute of TechnologyHarbinHeilongjiang150001 China School of Materials Science and Engineering Harbin Institute of TechnologyHarbinHeilongjiang150001 China State Key Laboratory of Luminescent Materials and Devices South China University of TechnologyGuangzhouGuangdong510640 China Institute of Advanced Technology Heilongjiang Academy of SciencesHarbinHeilongjiang150020 China

Inverted perovskite solar cells(PerSCs)are a highly promising candidate in the photovoltaic field due to their low-temperature fabrication process,negligible hysteresis,and easy integration with Si-based solar cells.A cathode interlayer(CIL)is necessary in the development of inverted devices to reduce the trap density and energy barrier between the electron transport layer(ETL)and the electrode.However,most CILs are highly thickness-sensitive due to low conductivity and poor film-forming.In this study,we report on a self-doping perylene imide-based ionene polymer(PNPDIN)used as CIL material to modify electrode in inverted PerSCs.PNPDIN exhibits high conductivity and a good solubility in polar solvent,which results in an improved power conversion efficiency(PCE)from 10.05%(device without a CIL)to 16.97%.When the blend of PNPDIN and Bphen was used as a mixed CIL,the PCE of PerSCs can be further increased to 21.28%owing to the excellent morphology and matched energy level.More importantly,the PCE of the device is highly tolerant to the thickness of the mixed CIL,which benefited from the high conductivity of PNPDIN.This development is expected to provide an excellent mixed CIL material for roll-to-roll processing efficient and stable inverted PerSCs.

关键词： perylene diimide Perovskite solar cells Interface engineering Cathode interlayer Thickness-independent

Highly emissive perylene diimide-based bowtie-shaped metallacycles

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Chinese Chemical Letters 2023年第4期34卷 296-299页

作者： Yali Hou Ruping Shi Hongye Yuan Mingming Zhang State Key Laboratory for Mechanical Behavior of Materials Shaanxi International Research Center for Soft MatterSchool of Materials Science and EngineeringXi’an Jiaotong UniversityXi’an 710049China

Metallacycles hold great promise for fluorescence-based sensing due to their synthetic advantages and unique physicochemical properties. However, it remains highly challenging to develop a versatile methodology for constructing highly emissive metallacycles with targeted functionalities and therefore soughtafter properties. Herein, we report a general strategy to construct a series of highly emissive perylene diimide-based metallacycles via the self-assembly of perylene diimide-based tetrapyridyl ligand with different dicarboxylic ligands featuring fixed angles and cis-Pt(PEt_(3))_(2)(OTf)_(2). Single crystal X-ray diffraction analyses verify the formation of bowtie-like metallacycles with two triangular cavities. Notably, the fluorescence quantum yields of most assemblies exceed 98%, amongst the highest values for metallacycles.Additionally, such metallacycles exhibit sensitive fluorescence responses toward picric acid with a detection limit of 2.8 × 10^(-6)mol/L. This study not only provides a rational strategy for preparing highly emissive bowtie-shaped metallacycles, but also sheds light on their usage in the detection of picric acid and associated compounds.

关键词： Fluorescence materials Emissive metallacycles Self-assembly perylene diimide Picric acid sensing

perylene diimide self-assembly: From electronic structural modulation to photocatalytic applications

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Journal of Semiconductors 2020年第9期41卷 99-125页

作者： Weiqin Wei Shuxin Ouyang Tierui Zhang College of Chemistry Central China Normal UniversityWuhan 430079China

As an emerging organic semiconductor,perylene diimide(PDI)self-assembly has attracted tremendous attention in the aspects of solar cells,sensors,fluorescence probes and n-transistors,etc.In term of photocatalysis,various photocatalysts based on PDI self-assembly exhibit some unique properties,such as intrinsicΠ-Πstacking structure,fast internal charge transfer,band-like electronic structure,flexible structural modifiability,well-defined morphological adjustability and excellent light absorption.This paper mainly presents recent progress on PDI self-assembly regarding how to regulate the electronic structure of PDI self-assembly.In addition,the photocatalytic applications of PDI self-assembly and its complexes were reviewed,such as environmental remedy,energy productions,organic synthesis and photodynamic/photothermal therapy,further highlighting related photocatalytic mechanisms.Finally,the review contents and some perspectives on photocatalytic research of PDI selfassembly were summarized,and some key scientific problems were put forward to direct related photocatalytic research in future.

关键词： perylene diimide self-assembly photocatalysis Π-Πstacking electron transfer

A Red-Emissive Sextuple Hydrogen-Bonding Self-Assembly Molecular Duplex Bearing perylene diimide Fluorophores for Warm-White Organic Light-Emitting Diode Application

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Chinese Journal of Chemistry 2016年第4期34卷 387-396页

作者： Hui Zeng Qingyu Huang Jingjing Liu Yan Huang Jie Zhou Suling Zhao Zhiyun Lu Key Laboratory of Green Chemistry and Technology of Ministry of Education College of Chemistry Sichuan University Chengdu Sichuan 610064 China Key Laboratory of Luminescence and Optical Information (Min&try of Education) Institute of Optoelectronics Technology Beijing Jiaotong University Beijing 100044 China

A novel sextuple hydrogen-bonding （HB） self-assembly molecular duplex bearing red-emitting perylene diimide （PDI） fluorophores, namely PDIHB, was synthesized, and its molecular structure was confirmed by IH NMR, 13C NMR, TOF-MS and 2D NMR. Compared with the small molecular reference compound PDI, PDIItB shows one time enhanced fluorescence efficiency in solid state （4.1% vs. 2.1%）. More importantly, the presence of bulky HB oli- goamide strands in PDIHB could trigger effective spatial separation between guest and host fluorophores in thin solid film state, hence inefficient energy transfer occurs between the blue-emitting host 2TPhNII/B and red guest PDIHB in the 2 wt% guest/host blending film. As a result, a solution-processed organic light-emitting diode （OLED） with quite simple device structure of ITO/PEDOT：PSS （40 nm）/PVK （40 nm）/PDIHB （2 wt%）： 2TPhNII-IB （50 nm）/LiF （0.8 nm）/A1 （100 nm） could emit bias-independent warm-white electroluminescence with stable Commission Intemationale de L＇Eclairage coordinates of （0.42, 0.33）, and the maximum brightness and current efficiency of this device are 260 cdom-2 and 0.49 cd·A-1, respectively. All these results indicated that HB self-assembly supramolecular fluorophores could act as prospective materials for white OLED application.

关键词： hydrogen-bonding self-assembly duplex perylene diimide inefficient energy transfer warm-whiteorganic light-emitting diode

Effect of Fluorination on Aggregate Structure of perylene diimide

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Chinese Chemical Letters 2004年第5期15卷 575-578页

作者： MinMinSHI HongZhengCHEN JingZhiSUN JianYE MangWANG DepartmentofPolymerScienceandEngineering StateKeyLabofSiliconMaterialsZhejiangUniversityHangzhou310027

The effect of fluorination on the aggregate structure of a novel fluorinated perylene diimide, N, N'-diperfluorophenyl-3, 4, 9, 10-perylenetetracarboxylic diimide 1, was investigated by UV-Vis absorptions and the conformation simulations from AM1 semi-empirical quantum mechanics modeling. The results showed that in the solid film 1 molecules stacked with the perfluorinated phenyl groups straightly over or below the perylene cores of the adjacent 1 molecules.

关键词： Fluorination perylene diimide aggregate structure absorption.

Symmetry-Induced Orderly Assembly Achieving High-Performance perylene diimide-Based Nonfullerene Organic Solar Cells

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CCS Chemistry 2021年第8期3卷 78-84页

作者： Shangshang Chen Dong Meng Jiachen Huang Ningning Liang Yan Li Feng Liu He Yan Zhaohui Wang Department of Chemistry Energy Institute and Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and ReconstructionHong Kong University of Science and TechnologyClear Water BayHong Kong 999077 Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Organic SolidsCAS Center of Excellence in Molecular ScienceInstitute of ChemistryChinese Academy of SciencesBeijing 100190 Key Laboratory of Organic Optoelectronics and Molecular Engineering Department of ChemistryTsinghua UniversityBeijing 100184 Department of Polymer Science and Engineering School of Chemistry and Chemical EngineeringShanghai Jiao Tong UniversityShanghai 200240

Controllable assembly of organic semiconductors has opened an avenue for an in-depth perception of their structure–property relationships;however,a detailed investigation of their molecular controllability remains challenging.Discerning the assembly of organic semiconductors could enable the attainment of a significant improvement of performance.

关键词： perylene diimide smallmolecule acceptors organic solar cells molecule assembly

Efficient and stable photocatalytic H2 evolution by self-assembly of zirconium(IV) coordination with perylene diimide supramolecules

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Efficient and stable photocatalytic H2 evolution by self-ass...

Novel organic/inorganic PDI-Urea/BiOBr S-scheme heterojunction for improved photocatalytic antibiotic degradation and H_(2)O_(2) production

第八届新型太阳能材料科学与技术学术研讨会

作者： Haoran Ding Jianli Hua Key Laboratory for Advanced Materials Institute of Fine ChemicalsSchool of Chemistry and Molecular EngineeringEast China University of Science and Technology

Wide spectral response and rapid separation and transfer of charge carriers are critical to the high activity of photocatalysts. Metal ions can work as an electron mediator to promote charge transfer. Therefore, we adopted the strategy of forming coordination bonds between metal cations of zirconium(IV) with a perylene diimide(PDI)-based organic supramolecular system to broaden the absorption spectrum and facilitate separation of photoinduced charges. We successfully prepared a series of doped supramolecular photocatalysts P-PMPDI containing different contents of Zr cations via phosphonate/ZrIV coordination bonds, and among them, P-PMPDI-Zr(Zr : P-PMPDI = 0.25 : 1) exhibited the highest activity toward the hydrogen evolution reaction(HER) of 2.52 mmol h(50.46 mmol g h) with an apparent quantum yield of 11.7% at 630 nm and good stability. This photocatalysts offer a useful strategy for optimizing the activity and stability of organic photocatalytic systems through the rational design of coordination bonds between metal cations and supramolecular system.

关键词： supramolecular photocatalysts photocatalytic H2 evolution perylene diimide

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Chinese Chemical Letters 2022年第12期33卷 5200-5207页

作者： Weiwei Wang Xibao Li Fang Deng Jiyou Liu Xiaoming Gao Juntong Huang Jilin Xu Zhijun Feng Zhi Chen Lu Han School of Materials Science and Engineering Nanchang Hangkong UniversityNanchang 330063China Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle Nanchang Hangkong UniversityNanchang 330063China Department of Chemistry and Chemical Engineering Shaanxi Key Laboratory of Chemical Reaction EngineeringYan'an UniversityYan'an 716000China School of Materials and Metallurgy University of Science and Technology LiaoningAnshan 114051China

The matched energy band structure and efficient carrier separation efficiency are the keys to heterogeneous photocatalytic reactions.A novel organic/inorganic step scheme(S-scheme)heterojunction PDI-Urea/BiOBr composite photocatalyst was constructed by simple solvothermal reaction combined with in-situ growth strategy.The composite photocatalyst not only has high chemical stability,but also can generate and accumulate a large number of active species(h^(+),·O_(2)^(-),·OH,H_(2)O_(2)).PDI-Urea/BiOBr showed higher photocatalytic activity for the degradation of antibiotic such as ofloxacin(OFLO),tetracycline(TC)and the production of H_(2)O_(2) in the spectral range of 400-800 nm.The apparent rate constant of 15%PDI-Urea/BiOBr for photocatalytic degradation of TC(or OFLO)was 2.7(or 2.5)times that of pure BiOBr and 1.7(or 1.8)times that of pure PDI-Urea.The H_(2)O_(2) evolution rate of 15%PDI-Urea/BiOBr was 2.5 times that of PDI-Urea and 1.5 times that of BiOBr,respectively.This work has formed a mature S-scheme heterojunction design thought and method,which offers new visions for the development of heterogeneous photocatalysts.

关键词： Photocatalysis perylene diimide Bismuth bromide oxide S-scheme heterojunction Antibiotic