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An asymmetric non-fused electron-deficient building block for low-cost polymer acceptor in all-polymer solar cells

中国科学:化学英文版 2023年第9期66卷 2626-2633页

作者： Haiqin Xiao Linfeng Yu Zhiliang zhang Haiyan Liang Yu Shi Xia Guo Maojie Zhang Yongfang Li Laboratory of Advanced Optoelectronic Materials Suzhou Key Laboratory of Novel Semiconductor-optoelectronics Materials and DevicesCollege of ChemistryChemical Engineering and Materials ScienceSoochow UniversitySuzhou 215123China National Engineering Research Center for Colloidal Materials School of Chemistry&Chemical EngineeringShandong UniversityJinan 250100China Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Organic SolidsInstitute of ChemistryChinese Academy of SciencesBeijing 100190China

The development of polymerized fused-ring small molecule acceptors(FRA-PAs) has boosted the performance of all-polymer solar cells(all-PSCs).However,these FRA-PAs suffer from lengthy synthesis steps and high production costs due to the high degree of synthetic complexity for fused-ring small molecule acceptors(FRAs).Furthermore,most FRA-PAs exhibit strong batch-to-batch variation,limiting further industrial applications.Herein,we designed and synthesized asymmetric non-fused electron-deficient building block TIC-Br with a simple structure(only three synthetic steps),showing a planar configuration,excellent electron affinity,and large dipole moment.A simple polymer acceptor PTIB was further developed by polymerization of TIC-Br and sensitized fluorinated-thienyl benzodithiophene(BDT-TF-Sn).PTIB exhibits a broad absorption from 300 to 800 nm,a suitable lowest unoccupied molecular orbital(LUMO) energy level of-3.86 e V,and moderate electron mobility(1.02×10^(-4)cm^(2)V^(-1)s^(-1)).When matched with PM6,the device achieved the best PCE of 10.11%with a high V_(OC) of 0.97 V,which is one of the highest among those reported all-PSCs.More importantly,PTIB exhibits a lower synthetic complexity index(SC=35.0%)and higher figure-of-merit values(FOM=29.0%) than all the reported high-performance PAs.The polymer also exhibits excellent batch-to-batch reproducibility and great potential for scale-up fabrication.This study indicates that TIC-Br is a promising building block for constructing low-cost polymer acceptors for large-scale applications in all-PSCs.

关键词： non-fused electron-deficient building block low-cost polymer acceptors batch-to-batch reproducibility all-polymer solar cells

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π-Extended End Groups Enable High-Performance All-Polymer Solar Cells with Near-Infrared Absorption

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Chinese Journal of Chemistry 2023年第23期41卷 3261-3267页

作者： Linfeng Yu Haiqin Xiao Yu Shi Xia Guo Xinxin Xia Xinhui Lu Maojie Zhang Laboratory of Advanced Optoelectronic Materials Suzhou Key Laboratory of Novel Semiconductor-optoelectronics Materials and Devices College of ChemistryChemical Engineering and Materials ScienceSoochow UniversitySuzhouJiangsu215123 China National Engineering Research Center for Colloidal Materials School of Chemistry & Chemical EngineeringShandong UniversityJinanShandong250100 China Department of Physics Chinese University of Hong KongNew TerritoriesHong Kong999077 China

Narrow-bandgap n-type polymers are essential for advancing the development of all-polymer solar cells(all-PSCs).Herein,we developed a novel polymer acceptor PNT withπ-extended 2-(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)malononitrile(CPNM)end groups.Compared to commonly used 2-(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1ylidene)malononitrile(IC)units,CPNM units have a further extended fused ring,providing the PNT polymer with extended absorption into the near-IR region(903 nm)and exhibiting a narrow optical bandgap(1.37 eV).Furthermore,PNT exhibits a high electron mobility(6.79×10^(−4) cm^(2)·V^(−1)·S^(−1))and a relatively high-lying lowest unoccupied molecular orbital(LUMO)energy level of−3.80 eV.When blended with PBDB-T,all-PSC achieves a power conversion efficiency(PCE)of 13.7%and a high short-circuit current density(JSC)of 24.4 mA·cm^(−2),mainly attributed to broad absorption(600—900 nm)and efficient charge separation and collection.Our study provides a promising polymer acceptor for all-PSCs and demonstrates thatπ-extended CPNM units are important to achieve high-performance for all-PSCs.

关键词： Polymer acceptors π-Extended end groups High short-circuit current density Narrow-bandgap All-polymer solar cells

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A Non-Halogenated Polymer Donor Based on Imide Unit for Organic Solar Cells with Efficiency Nearly 16%

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Chinese Journal of Chemistry 2023年第17期41卷 2095-2102页

作者： Liu zhang Zhiliang zhang Haiyan Liang Xia Guo Maojie Zhang Laboratory of Advanced Optoelectronic Materials Suzhou Key Laboratory of Novel Semiconductor-optoelectronics Materials and DevicesCollegeof ChemistryChemical Engineeringand Materials ScienceSoochow UniversitySuzhouJiangsu 215123China National Engineering Research Center for Colloidal Materials School of Chemistry&Chemical EngineeringShandong UniversityJinanShandong 250100China

Comprehensive Summary,Non-halogenated polymers have great potential in the commercialization of organic solar cells(OSCs)due to their advantages in the manufacturing process.However,high-performance donor polymers are limited to a small amount of building blocks.Herein,we utilize as building block 4H-dithieno[3,2-e:2',3'-g]isoindole-4,6(5H)-dione(DTID)to design and synthesize a relevant non-halogenated polymer PBTID for active layers in OSCs.PBTID exhibits a strong absorption in the wavelength range of 400—600 nm with a distinctly wide optical bandgap of 2.06 eV,a low-lying highest occupied molecular orbital(HOMO)energy level of−5.53 eV.In addition,this polymer has a very strong aggregation effect in solution and could form nanoscale fibrils in the neat film.Consequently,when blended with the non-fullerene acceptor Y6,the devices achieve a prominent PCE of 15.8%with a high Voc of 0.87 V.The Voc and PCE values are one of the highest values in the non-halogenated polymer donor-based OSCs reported to date.

关键词： Dithienophthalimide Non-halogenated polymer donor Building blocks High efficiency Organic solar cells Aggregation

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Tandem organic solar cells with 20.6% efficiency enabled by reduced voltage losses

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National Science Review 2023年第6期10卷 215-225页

作者： Jianqiu Wang Zhong Zheng Pengqing Bi Zhihao Chen Yafei Wang Xiaoyu Liu Shaoqing zhang Xiaotao Hao Maojie Zhang Yongfang Li Jianhui Hou State Key Laboratory of Polymer Physics and Chemistry Beijing National Laboratory for Molecular Sciences Institute of Chemistry Chinese Academy of Sciences Laboratory of Advanced Optoelectronic Materials Suzhou Key Laboratory of Novel Semiconductoroptoelectronics Materials and Devices College of Chemistry Chemical Engineering and Materials Science Soochow University School of Chemistry and Biology Engineering University of Science and Technology Beijing School of Physics State Key Laboratory of Crystal Materials Shandong University University of Chinese Academy of Sciences CAS Key Laboratory of Organic Solids Beijing National Laboratory for Molecular Sciences Institute of Chemistry Chinese Academy of Sciences

Large voltage losses are the main obstacle for achieving high efficiency in organic solar cells(OSCs).Here we construct ternary OSCs by introducing an asymmetric small molecule acceptor AITC into PBDB-TCl:BTP-eC9 system and demonstrate the effectiveness in simultaneously decreasing energy disorder and non-radiative voltage losses.It is found that the introduction of AITC can modify domain size and increase the degree of crystallinity,which enhances open-circuit voltage and power conversion efficiency(19.1%,certified as 18.9%).Inspiringly,an output efficiency of 20.6% of the constructed tandem OSCs based on PBDB-TCl:AITC:BTP-eC9 ternary active layer output a recorded efficiency of 20.6%(certified as 20.3%),which is the highest value in OSCs field to date.This work demonstrates that decreasing the voltage losses by ternary strategy and constructing of tandem architecture are effective approaches towards improving photovoltaic performance.

关键词： organic solar cells power conversion efficiency voltage losses tandem cells ternary strategy

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Effect of Fluorination on the Photovoltaic Properties of Medium Bandgap Polymers for Polymer Solar Cells

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Chinese Journal of Chemistry 2018年第6期36卷 502-506页

作者： Huan Guo Wanbin Li Chunmei Chang Xia Guo Maojie Zhang Laboratory of Advanced Optoelectronic Materials College of Chemistry Chemical Engineering and Materials Science Soochow University Suzhou Jiangsu 215123 China

Fluorination of conjugated polymers is one of the effective strategies to tune the molecular energy levels and morphology for high efficient polymer solar cells （PSCs）. Herein, two novel donor-acceptor conjugated polymers, PffBT and PBT, based on bis（3,5-bis（hexyloxy）phenyl）benzo[1,2- b：4,5-b＇]dithiophene and benzo[c][1,2,5]thiadiazole （BT） with or without fluorination, respectively, were synthesized, and their photovoltaic properties were compared. The polymer PffBT based on fluorinated BT showed lower frontier energy levels, improved polymer ordering, and a well-developed fibril structure in the blend with PC71BM. As a result, the PSCs based on PffBT/PC71BM exhibit a superior power conversion efficiency （PCE） of 8.6% versus 4.4% for PBT-based devices, due to a high space charge limit current （SCLC） hole mobility, mixed orientation of polymer crystals in the active layer, and low bimolecular recombination.

关键词： benzo[c][1 2 5]thiadiazole conjugated polymers fluorination polymer solar cells power conversion efficiency

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Tuning Aggregation Behavior of Polymer Donor via Molecular-Weight Control for Achieving 17.1%Efficiency Inverted Polymer Solar Cells

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Chinese Journal of Chemistry 2021年第7期39卷 1941-1947页

作者： Qi Liu Jin Fang Jingnan Wu Lei Zhu Xia Guo Feng Liu Maojie Zhang Laboratory of Advanced Optoelectronic Materials College of ChemistryChemical Engineering and Materials ScienceSoochow UniversitySuzhouJiangsu 215123China Frontiers Science Center for Transformative Molecules School of Chemistry and Chemical EngineeringShanghai Jiao Tong UniversityShanghai 200240China

Main observation and conclusion Recently,the polymer solar cells(PSCs)based on the PM6 and small molecular acceptor(SMA)Y6 have attracted considerable attention in this community for their outstanding photovoltaic per... 详细信息

关键词： Organic solar cells Power conversion efficiency Polymers Donor-acceptor systems Molecular weight

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Functional nanoemulsions: Controllable low-energy nanoemulsification and advanced biomedical application

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Chinese Chemical Letters 2024年第2期35卷 57-69页

作者： Maojie Zhang Qiang Cao Yuming Yuan Xiaohan Guo Dawei Pan Rui Xie Xiaojie Ju Zhuang Liu Wei Wang Liangyin Chu College of Engineering Sichuan Normal UniversityChengdu 610101China School of Chemical Engineering Sichuan UniversityChengdu 610065China State Key Laboratory of Polymer Materials Engineering Sichuan UniversityChengdu 610065China

Nanoemulsions are widely used as advanced pharmaceutical delivery systems in biomedical field, due to their high encapsulation efficiency and good therapy efficacy.Nanoemulsification techniques that produce nanoemulsions with controllable sizes and compositions are promising for creating advanced nanoemulsion systems for pharmaceutical delivery.This review summarizes recent advances on low-energy emulsification techniques for producing nanoemulsions, and the use of these nanoemulsions as advanced pharmaceutical delivery systems and as templates to create drug-loaded functional particles for biomedical application.First, nanoemulsification techniques that utilize elaborate interfacial physics/chemistry and micro-/nano-fluidics, featured with relatively-low energy input, to produce nanoemulsions with controllable sizes and compositions, are introduced.Uses of these nanoemulsions to create nanoemulsionincorporated milli-particles, drug-loaded nanoparticles and nanoparticle-incorporated microparticles with sizes ranging from several millimeters to sub-10 nm are emphasized.Flexible and efficient use of the nanoemulsions, functional nanoparticles and milli-/micro-particles integrated with nanoemulsions or nanoparticles for advanced pharmaceutical delivery in biomedical field are highlighted, with focus on how the interplay between their sizes and compositions achieve desired pharmaceutical-delivery performances.Finally, perspectives on further advances on the controllable production of nanoemulsions are provided.

关键词： Nanoemulsions Interfaces Drug delivery Template synthesis Nanoparticles

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A Non-Fullerene Acceptor with Chlorinated Thienyl Conjugated Side Chains for High-Performance Polymer Solar Cells via Toluene Processing

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Chinese Journal of Chemistry 2020年第7期38卷 697-702页

作者： Cuangwei Li Jingnan Wu Jin Fang Xia Guo Lei Zhu Feng Liu Maojie Zhang Yongfang Li Laboratory of Advanced Optoelectronic Materials College of ChemistryChemical Engineering and Materials ScienceSoochow UniversitySuzhouJiangsu 215123China Department of Physics and Astronomy and Collaborative Innovation Center of IFSA(CICIFSA) Shanghai Jiao Tong UniversityShanghai 200240China Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Organic SolidsInstitute of ChemistryChinese Academy of SciencesBeijing 100190China

Small molecular acceptors(SMAs)BTC-2F and BTH-2F,based on heptacyclic benzodi(cyclopentadithiophene)electron-donating core(CBT)with chlorinated-thienyl conjugated and thienyl conjugated side chains,respectively,are designed and synthesized.Compared with non-chlorine acceptor BTH-2F,BTC-2F exhibits slightly blue-shifted absorption spectra,similar the lowest unoccupied molecular orbital(LUMO)(-3.91 eV);deeper highest occupied molecular orbital(HOMO)energy level and higher electron mobility than that of BTH-2F.PM6,a wide bandgap polymer,is selected as the donor material to construct bulk heterojunction polymer solar cells processed with nonhalogenated solvent toluene.The optimized PM6:BTC-2F-based device presents a 12.9%power conversion efficiency(PCE),while the PCE of PM6:BTH-2F-based device is only 11.3%.The results suggest that it is an effective strategy to optimize the photoelectric properties of SMAs by incorporating chlorine atom into the conjugated side chains.

关键词： conjugated chlorine chains

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Modulating Crystallinity and Miscibility via Side-chain Variation Enable High Performance All-Small-Molecule Organic Solar Cells

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Chinese Journal of Chemistry 2021年第8期39卷 2147-2153页

作者： Yang Wang Qunping Fan Yulong Wang Jin Fang Qi Liu Lei Zhu Jinjing Qiu Xia Guo Feng Liu Wenyan Su Maojie Zhang Laboratory of Advanced Optoelectronic Materials College of ChemistryChemical Engineering and Materials ScienceSoochow UniversitySuzhouJiangsu 215123China Department of Chemistry City University of Hong KongKowloon 999077Hong KongChina Frontiers Science Center for Transformative Molecules School of Chemistry and Chemical EngineeringShanghai Jiao Tong UniversityShanghai 200240China Guangdong Provincial Key Laboratory of Optical Fiber Sensing and Communications Siyuan LaboratoryDepartment of PhysicsJinan UniversityGuangzhouGuangdong 510632China

Side-chain engineering as one of the most important molecular design strategies has been widely used to improve photovoltaic effi-ciency of active layer materials.Herein,a series of acceptor-n-donor-n-acceptor typed small molecule(SM)-donors(SL1,SL2,SL3,and SL4),on the basis of high-performance SM-donor BTTzR(SL1)with thiazolo[5,4-d]thiazole as the n-bridging units and 3-butylrho-danine as the terminal electron-withdrawing groups,were designed and synthesized to study the effect of the side-chain substitu-tions of BDT-T on the photovoltaic performanee.

关键词： Organic solar cells Small molecule donor Substituent effects Aggregation Solvent effects

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A Noncovalently Fused-Ring Asymmetric Electron Acceptor Enables Efficient Organic Solar Cells

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Chinese Journal of Chemistry 2021年第10期39卷 2685-2691页

作者： Ji Lin Qing Guo Qi Liu Junfang Lv Haiyan Liang Yang Wang Lei Zhu Feng Liu Xia Guo Maojie Zhang Laboratory of Advanced Optoelectronic Materials College of ChemistryChemical Engineering and Materials ScienceSoochow UniversitySuzhouJiangsu215123 China Frontiers Science Center for Transformative Molecules School of Chemistry and Chemical EngineeringShanghai Jiao Tong UniversityShanghai 200240China Henan Institute of Advanced Technology Zhengzhou UniversityZhengzhouHenan450003 China

Main observation and conclusion Recently,the asymmetric nonfullerene acceptors(NFAs)with acceptor-donor-acceptor(A-D-A)structure have been developed rapidly,especially for the modification of asymmetric core,asymmetric side chains and asymmetric end groups.In this work,a novel asymmetric A-D-π-A type NFA with a noncovalently fused-ring core named PIST-4F is synthesized,containing an indacenodithieno[3,2-b]dithiophene(IDT),two strong electron-withdrawing end groups and an alkylthio-substituted thiopheneπ-bridge.Benefiting from the S···S noncovalent interaction between the sulfur atom onπ-bridge and the adjacent thiophene in IDT,the PIST-4F presents nearly planar geometry and extended conjugated area,resulting in the optimized electronic properties,charge transport,and film morphology compared to the symmetric NFA PI-4F.As a result,PM6:PIST-4F-based devices achieve a higher power conversion efficiency(PCE)of 13.8%,while the PM6:PI-4F-based devices only show a PCE of 7.1%.Notably,the PM6:PIST-4F-based devices processed with nonhalogen solvent toluene exhibit an excellent PCE as high as 13.1%.These results indicate that PIST-4F is an effective acceptor for high-efficiency organic solar cells.

关键词： Organic solar cells Asymmetric synthesis π-bridge Noncovalent interactions Electron transport

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