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Manipulating molecular aggregation and crystalline behavior of A-DA’D-A type acceptors by side chain engineering in organic solar cells

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Aggregate 2022年第3期3卷 13-18页

作者： Wei Liu Rui Zhang Qingya Wei Can Zhu Jun Yuan Feng Gao Yingping Zou State Key Laboratory of Powder Metallurgy College of Chemistry and Chemical EngineeringCentral South UniversityChangshaP.R.China Department of Physics Chemistry and Biology(IFM)Linköping UniversityLinköpingSweden Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Organic SolidsInstitute of ChemistryChinese Academy of SciencesBeijingP.R.China

Alkyl chains engineering plays an important role in photovoltaic materials for organic solar ***,three A-DA’D-A(acceptor–donor–acceptor’–donor–acceptor)type acceptors named Y6,Y6-C4,and Y6-C5 with different branching position on the pyrrole motif are discussed and the relationship between molecular aggregation,crystalline,and device performance are systematically *** distance between the branching position and the main backbone affects their optical absorption and energy levels.Y6-C4 and Y6-C5 with the branching position at the fourth and fifth carbon of the alkyl chain show blue-shifted absorption and increased electrochemical bandgaps,compared with Y6 with the branching position at the second carbon of the alkyl side *** addition,this distance influences the molecular aggregation and crystalline behavior of the donor/acceptor *** with Y6-C4,Y6-C5 possesses a stronger crystalline and aggregate ability in the blends with a lower non-radiative energy loss,which results in a higher open circuit voltage(Voc)of 0.88 ***,Y6-C5-based binary device achieved a high power conversion efficiency up to 16.73%with afill factor(FF)of *** results demonstrate that the side chain engineering is an effective strategy for tuning the molecular aggregation and crystalline to improve photovoltaic performance of the A-DA’D-A type acceptors.

关键词： A-DA’D-A type acceptor aggregation side chain engineering

Silane or Siloxane-side-chain engineering of Photovoltaic Materials for Organic Solar Cells

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Chinese Journal of Chemistry 2023年第24期41卷 3703-3713页

作者： Qian Wang Xu Zhang Wentao Zou Huajun Xu Yuanyuan Kan Yanna Sun Ke Gao Shandong Provincial Key Laboratory for Science of Material Creation and Energy Conversion Science Center for Material Creation and Energy ConversionInstitute of Frontier and Interdisciplinary ScienceShandong UniversityQingdaoShandong266237 China

With the tactful material design,skillful device engineering,and in-depth understanding of morphology optimization,organic solar cells (OSCs) have achieved considerable ***,OSCs have reached high power conversion efficiencies (PCEs) exceeding 19%.Especially,continuously emerging new materials have been considered as one of the key factors to improve the PCEs of *** molecular design strategies,side-chain engineering is an easy and commonly-used means which can optimize the solubility,alter intermolecular stacking arrangement,fine-tune the open circuit voltage (VOC),thus ultimately improve the *** hybrid side chains,silane and siloxane side chains have considerable effects,not only in increasing the carrier mobility and tuning the energy level,but also in affecting the crystallinity and molecular *** this review,the latest developments in photovoltaic materials based on silane and siloxane side chains are presented to illustrate the structure-property *** review comprehensively includes silane-side based polymer/small molecule donors;siloxane-side based polymer/small molecule donors,and polymer/small molecule *** the similarities and differences between these two side chains are ***,the possible applications and future prospects of silane and siloxane side chains are presented.

关键词： Organic solar cell Silane side chain Siloxane side chain side chain engineering High performance Batteries Applications

19.3% Efficiency ternary organic solar cells enabled by the alkyl side-chain effect of guest non-fullerene acceptors

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Science China Chemistry 2024年第8期67卷 2686-2693页

作者： Hongqian Wang Sijian Wu Daobin Yang Xueliang Yu Shuncheng Yang Pengfei Ding Pengyu Yan Zaifei Ma Jianfeng Zhang Ziyi Ge School of Materials Science and Chemical engineering Ningbo UniversityNingbo 315211China Zhejiang engineering Research Center for Energy Optoelectronic Materials and Devices Ningbo Institute of Materials Technology and EngineeringChinese Academy of SciencesNingbo 315201China State Key Laboratory for Modification of Chemical Fibers and Polymer Materials Center for Advanced Low-dimension MaterialsCollege of Materials Science and EngineeringDonghua UniversityShanghai 201620China Center of Materials Science and Optoelectronics engineering University of Chinese Academy of SciencesBeijing 100049China

The effect of side-chain engineering of conjugated molecules on the morphology and device performance in binary organic solar cells has been widely investigated. However, this relationship has hardly been studied in the guest components of ternary organic solar cells. In this study, a family of non-fullerene guest acceptors, namely XY-3, XY-5 and XY-7, with hydrogen substituent,straight and branched alkyl chains on the bithiophene units, respectively, were designed and synthesized to understand their effects on aggregation properties and device performance. The straight and branched alkyl chains on the bithiophene units result in sightly blue-shifted absorption compared to the hydrogen substituent and the XY-7 demonstrates the most appropriate phase separation scale and the most balanced charge transport. Consequently, the OSCs based on D18:e C9:XY-7 achieve a high shortcircuit current density(JSC) and fill factor(FF), while maintaining the enhancement of the open-circuit voltage(VOC) achieving an efficiency of 19.32%, exceeding those of D18:e C9, D18:e C9:XY-3, D18:e C9:XY-5(PCE:18.28%, 19.04%, 18.75%, respectively). These results highlight that the side-chain engineering of Y series non-fullerene acceptors as the guest acceptors has great potential in optimizing morphology properties and promoting photovoltaic performance.

关键词： organic solar cells side chain engineering ternary strategy non-fullerene energy losses

通过侧链工程提高A-D-A'-D-A型非稠环电子受体的光伏性能

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Science China Materials 2024年第5期67卷 1594-1601页

作者：周霞魏文魁庞淑婷袁熙越李俊宇黄飞曹镛段春晖 School of New Energy Ningbo University of TechnologyNingbo315336China Molecular Materials and Nanosystems&Institute for Complex Molecular Systems Eindhoven University of Technology5600 MBEindhovenNetherlands Institute of Polymer Optoelectronic Materials and Devices State Key Laboratory of Luminescent Materials and DevicesSouth China University of TechnologyGuangzhou510640China

非稠环电子受体(NFREA)具有合成简单和结构修饰灵活的特点,是制备高性能低成本有机太阳电池(OSCs)的理想材料.本工作以不同侧链修饰的二氟苯并三氮唑(ffBTz)作为弱缺电子核(A’),分别设计合成了三种A-D-A’-D-A型NFREA,即ffBTz-BO、ffBT... 详细信息

非稠环电子受体(NFREA)具有合成简单和结构修饰灵活的特点,是制备高性能低成本有机太阳电池(OSCs)的理想材料.本工作以不同侧链修饰的二氟苯并三氮唑(ffBTz)作为弱缺电子核(A’),分别设计合成了三种A-D-A’-D-A型NFREA,即ffBTz-BO、ffBTz-EH和ffBTz-C4.其中,ffBTz-EH,由于其合适的侧链长度,在分子结晶度和分子堆积优势取向之间取得了平衡,从而获得了更高的电荷迁移率.并且得益于高效的电荷传输和最合适的相分离形貌,基于ffBTz-EH的OSC获得12.96%的最高能量转换效率,这也是A-D-A’-D-A型NFREA获得的最高效率之一.本研究表明,A’核心上的烷基侧链在调节分子结晶度、活性层形貌和进一步调控器件性能方面起着至关重要的作用,这为未来设计高效低成本的A-D-A’-D-A型非稠环电子受体提供了思路.

关键词： organic solar cells non-fused ring electron acceptors side chain engineering molecular orientation power conversion efficiency

Recent progress in design of conductive polymers to improve the thermoelectric performance

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Chinese Physics B 2022年第2期31卷 22-32页

作者： Zhen Xu Hui Li Lidong Chen State Key Laboratory of High Performance Ceramics and Superfine Microstructures Shanghai Institute of CeramicsChinese Academy of SciencesShanghai 200050China Center of Materials Science and Optoelectronics engineering University of Chinese Academy of SciencesBeijing 100049China

Organic semiconductors,especially polymer semiconductors,have attracted extensive attention as organic thermoelectric materials due to their capabilities for flexibility,low-cost fabrication,solution processability and low thermal ***,it is challenging to obtain high-performance organic thermoelectric materials because of the low intrinsic carrier concentration of organic *** main method to control the carrier concentration of polymers is the chemical doping process by charge transfer between polymer and ***,the deep understanding of doping mechanisms from the point view of chemical structure has been highly desired to overcome the bottlenecks in polymeric *** this contribution,we will briefly review the recently emerging progress for discovering the structure–property relationship of organic thermoelectric materials with high *** include some achievements about doping strategies to effectively modulate the carrier concentration,the design rules of building blocks and side chains to enhance charge transport and improve the doping ***,we will give our viewpoints on the challenges and opportunities in the field of polymer thermoelectric materials.

关键词： conductive polymer organic thermoelectric material chemical doping side chain engineering

Asymmetric molecular engineering in recent nonfullerene acceptors for efficient organic solar cells

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Chinese Chemical Letters 2023年第10期34卷 48-54页

作者： Jinsheng Song Zhishan Bo engineering Research Center for Nanomaterials Henan UniversityKaifeng 475004China Beijing Key Laboratory of Energy Conversion and Storage Materials College of ChemistryBeijing Normal UniversityBeijing 100875China College of Textiles&Clothing Qingdao UniversityQingdao 266071China

Nonfullerene acceptors(NFAs),which usually possess symmetric skeletons,have drawn great attention in recent years due to their pronounced advantages over the fullerene ***,breaking the symmetry of NFAs could fine tune the molecular dipole,solubility,energy level,intermolecular interaction,molecular packing,crystallinity,etc.,and give rise to improved photovoltaic ***,there are three main strategies for the design of asymmetric *** review highlights the recent advances of high-performance asymmetric NFAs and briefly outlooks the materials exploration for the future.

关键词： Asymmetric strategy Organic photovoltaics Nonfullerene acceptor side chain engineering Y-series acceptors

Ternary solvent-processed efficient organic solar cells based on a new A-DA'D-A acceptor derivative employing the 3^(rd)-position branching side chains on pyrroles

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Chinese Chemical Letters 2021年第1期32卷 229-233页

作者： Yu Chen Honggang Chen Huilan Guan Wei Liu Zhe Li Hui Liu Yongfang Li Yingping Zou College of Chemistry and Chemical engineering Central South UniversityChangsha 410083China School of Materials Science and engineering Zhengzhou UniversityZhengzhou 450001China Institute of Chemistry Chinese Academy of SciencesBeijing 100190China

Recent advances in non-fullerene acceptors(NFAs),typically Y6,have driven power conversion efficiency(PCE) of single-junction orga nic solar cells(OSCs) over 16%.Mea nwhile,it becomes essential to know how to adopt simple strategies to further improve device *** this work,a new A-DA'D-A acceptor derivative,Y19-N3 employing 3-ethylheptyl branched at the 3^(rd)-position instead of 2-ethylhexyl on the pyrroles of Y19 is *** selection of an appropriate solvent in casting device is implemented to maximize the photovoltaic ***-T:Y19-N3-based OSCs treated with a ternary solvent of CF/CB(1:3,v/v) and 0.8% DIO exhibit the optimal PCE of 13.77% here,with the significantly improved V_(oc)(0.78 V) and FF(0.72) as well as the high J_(sc)(24.46 mA/cm^(2)).Further characterizations indicate that this ternary solvent-treated PBDB-T/Y19-N3 film exhibits the more appropriate morphological features with the highly efficient charge generation and collection as well as the more balanced electron and hole *** work combines molecular design and device engineering to improve the photovoltaic properties,which is important to the development of OSCs.

关键词： Organic solar cells side chain engineering Ternary solvent Increased efficiency Balanced mobilities

18.55% Efficiency Polymer Solar Cells Based on a Small Molecule Acceptor with Alkylthienyl Outer side chains and a Low-Cost Polymer Donor PTQ10

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CCS Chemistry 2023年第4期5卷 841-850页

作者： Xiaolei Kong Jinyuan Zhang Lei Meng Chenkai Sun Shucheng Qin Can Zhu Jianqi Zhang Jing Li Zhixiang Wei Yongfang Li Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Organic SolidsInstitute of ChemistryChinese Academy of SciencesBeijing 100190 School of Chemical Science University of Chinese Academy of SciencesBeijing 100049 College of Chemistry Green Catalysis CenterZhengzhou UniversityZhengzhou 450001 CAS Key Laboratory of Nanosystem and Hierarchical Fabrication CAS Center for Excellence in NanPSCienceNational Center for NanPSCience and Technology100190 Beijing Key Laboratory of Photochemical Conversion and Optoelectronic Materials Technical Institute of Physics and ChemistryChinese Academy of SciencesBeijing 100190 Laboratory of Advanced Optoelectronic Materials Suzhou Key Laboratory of Novel Semiconductor Materials and DevicesCollege of ChemistryChemical Engineering and Materials ScienceSoochow UniversitySuzhouJiangsu 215123

The development of A-DA′D-A type small molecule acceptors(SMAs)has promoted the rapid progress of polymer solar cells(PSCs)in recent *** outer side chains on the terminal thiophene ring and inner side chains on nitrogen atoms of the pyrrole ring of the DA′D fused ring play important roles in the photovoltaic performance of the ***,we synthesized two new SMAs,2,2′-((2Z,2′Z)-((12,13-bis(2-ethylhexyl)-3,9-bis(4-(2-ethylhexyl)thiophen-2-yl)-12,13-dihydro-[1,2,5]thiadiazolo[3,4-e]thieno[2″,3″:4′,5′]thieno[2′,3′:4,5]pyrrolo[3,2-g]thieno[2′,3′:4,5]thieno[3,2-b]indole-2,10-diyl)bis(methaneylylidene))bis(5,6-difluoro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile(T2EH)and 2,2′-((2Z,2′Z)-((12,13-bis(2-ethylhexyl)-3,9-bis(3-(2-ethylhexyl)phenyl)-12,13-dihydro-[1,2,5]thiadiazolo[3,4-e]thieno[2″,3″:4′,5′]thieno[2′,3′:4,5]pyrrolo[3,2-g]thieno[2′,3′:4,5]thieno[3,2-b]indole-2,10-diyl)bis(methaneylylidene))bis(5,6-difluoro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene)(P2EH),with 2-ethylhexylβ-substituted thienyl or phenyl as the outer side chains,respectively,to improve the photovoltaic properties of the *** with P2EH,T2EH exhibits closerπ−πstacking,slightly red-shifted absorption,and higher electron ***,the active layer of T2EH blended with the low-cost polymer donor poly[(thiophene)-alt-(6,7-difluoro-2-(2-hexyldecyloxy)quinoxaline)](PTQ10)possesses higher mobilities,a longer lifetime,and less recombination of the charge carriers in comparison with that of the PTQ10:P2EH active ***,the PTQ10:T2EH-based PSCs showed an outstanding power conversion efficiency(PCE)of 18.55%,while the PSC based on PTQ10:P2EH displayed a PCE of 17.50%.Importantly,18.55%is the highest PCE in the PTQ10-based binary PSCs so *** results indicate that T2EH is one of the best SMAs for the PTQ10-based PSCs and is a promising SMA for the application of PSCs.

关键词： polymer solar cells A-DA′D-A type small molecule acceptors side chain engineering thiophene conjugated side chains

Low-Cost and High-Performance Polymer Solar Cells with Efficiency Insensitive to Active-Layer Thickness

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CCS Chemistry 2023年第12期5卷 2945-2955页

作者： Xiaolei Kong Jinyuan Zhang Lei Meng Chenkai Sun Xin Jiang Jianqi Zhang Can Zhu Guangpei Sun Jing Li Xiaojun Li Zhixiang Wei Yongfang Li Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Organic SolidsInstitute of ChemistryChinese Academy of SciencesBeijing 100190 School of Chemical Science University of Chinese Academy of SciencesBeijing 100049 College of Chemistry and Green Catalysis CenterZhengzhou UniversityZhengzhou 450001 CAS Key Laboratory of Nanosystem and Hierarchical Fabrication CAS Center for Excellence in NanoscienceNational Center for Nanoscience and TechnologyBeijing 100190 Key Laboratory of Photochemical Conversion and Optoelectronic Materials Technical Institute of Physics and ChemistryChinese Academy of SciencesBeijing 100190 Laboratory of Advanced Optoelectronic Materials Suzhou Key Laboratory of Novel Semiconductor-Optoelectronics Materials and DevicesCollege of ChemistryChemical Engineering and Materials ScienceSoochow UniversitySuzhou 215123

The power conversion efficiency(PCE)of polymer solar cells(PSCs)has recently increased quickly,propelling PSCs closer to large-scale ***,several critical issues,such as the cost of materials and the sensitivity of the PCE to active-layer thickness,must be addressed before industrial application can be realized on a large ***,we fabricated a high-performance ternary PSC based on a low-cost polymer donor PTQ10 and an A-DA’D-A-type small molecule acceptor(SMA)2,2'-((2Z,2'Z)-((12,13-bis(2-butyloctyl)-3,9-bis(4-(2-ethylhexyl)thiophen-2-yl)-12,13-dihydro-[1,2,5]thiadiazolo[3,4-e]thieno[2'',3'':4',5']thieno[2',3':4,5]pyrrolo[3,2-g]thieno[2',3':4,5]thieno[3,2-b]indole-2,10-diyl)bis(methaneylylidene))bis(5,6-difluoro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile(m-TEH)with a newA-DA’D-A-type SMA 2,2'-((2Z,2'Z)-((12,13-bis(2-butyloctyl)-3,9-bis(3-(2-ethylhexyl)phenyl)-12,13-dihydro-[1,2,5]thiadiazolo[3,4-e]thieno[2'',3'':4',5']thieno[2',3':4,5]pyrrolo[3,2-g]thieno[2',3':4,5]thieno[3,2-b]indole-2,10-diyl)bis(methaneylylidene))bis(5,6-difluoro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile(m-PEH)(with phenyl outer side chains)as the third *** from the good compatibility and the unique alignment of the energy levels between PTQ10 and the two SMAs,the ternary system showed favorable phase separation and dominant face-on orientation,exhibiting suitable film morphology and enhanced charge ***,the optimized ternary PSCs based on PTQ10∶m-TEH∶m-PEH(1.0∶0.9∶0.3,w/w/w)demonstrated an outstanding PCE of 19.34%,which is one of the highest PCEs reported for the single junction PSCs to *** importantly,the ternary PSCs demonstrated superior tolerance to the active-layer thickness and showed a high PCE of 18.02% with a high fill factor(FF)of 76.56% for the devices with the active-layer thickness even reaching 300 *** results indicate that the ternary devices based on PTQ10∶m-TEH∶m-PEH are highly

关键词： ternary polymer solar cells A-DA’D-A-type small molecule acceptors side chain engineering insensitive to active-layer thickness commercial application