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Selective fluorination on donor and acceptor for management of efficiency and energy loss in non-fullerene organic photovoltaics

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Science China Chemistry 2023年第4期66卷 1190-1200页

作者： You Chen Peng Lei Yanfang Geng Ting Meng Xiangyu Li Qingdao Zeng Qing Guo Ailing Tang Yufei Zhong erjun zhou CAS Center for Excellence in Nanoscience National Center for Nanoscience and TechnologyBeijing 100190China Center of Materials Science and Optoelectronics Engineering University of Chinese Academy of SciencesBeijing 100049China Henan Institute of Advanced Technology Zhengzhou UniversityZhengzhou 450003China School of Materials Science and Engineering Ningbo Tech UniversityNingbo 315100China

Although fluorination has been proved effective to modulate optoelectronic properties and film morphology,knowledge of managing power conversion efficiency(PCE)and energy loss(Eloss)of organic photovoltaics(OPVs)by selective fluorination on the donor and/or acceptor is lacking.Herein we designed and synthesized three 1,2,3-benzotriazole(BTA)-based linear polymers(PE45,PE46 and PE47)with different numbers of fluorine atom substitution on the conjugated phenyl side chain.Two classic non-fullerene acceptors(NFAs)Y5(without fluorination)and Y6(with fluorination)were utilized to manage the device efficiency and energy loss.The results revealed that increasing fluorine substitutions on polymer donor improved the OPV efficiencies when the fluorinated Y6 was used as the acceptor,whereas decreased the PCEs when the non-fluorinated Y5 was used as the acceptor.The energy loss declined with the growing fluorine substitutions on polymer donor,and Y5 systems gave the lower values in comparison with the corresponding Y6 cases.It turns out that PE47:Y6 achieved the highest PCE of 15.58%with an open-circuit voltage(VOC)of 0.84 V(Eloss=0.56 e V)due to the highest and balanced hole/electron mobilities,suppressed bimolecular recombination and fibril network morphology,which is the highest value in the BTA-based polymers.Furthermore,PE47:Y5 attained an ultralow non-radiative energy loss of 0.15 e V,which is one of the lowest values among the reported OPVs.Our work could not only give a direct path on how to manage the efficiency and energy loss by selective fluorination on donor and acceptor,but also show a deep understanding on charge generation,transport and collection induced by selective fluorination.

关键词： fluorination D-π-A polymer non-fullerene acceptor energy loss organic solar cells

Reconcile the contradictory wettability requirements for the reduction and oxidation half-reactions in overall CO_(2) photoreduction via alternately hydrophobic surfaces

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Journal of Energy Chemistry 2024年第6期93卷 202-212,I0006页

作者： Hailing Huo Ting Hu Chengxi Huang Fang Wu Tongyu Wang Xuan Liu Liang Zhang Qiang Ju Zhiqing Zhong Hongbin Xing erjun Kan Ang Li MIIT Key Laboratory of Semiconductor Microstructure and Quantum Sensing Nanjing University of Science and TechnologyNanjing 210094JiangsuChina College of Information Science and Technology Nanjing Forestry UniversityNanjing 210037JiangsuChina

The overall photocatalytic CO_(2) reduction reaction(OPCRR)that can directly convert CO_(2) and H_(2)O into fuels represents a promising renewable energy conversion technology.As a typical redox reaction,the OPCRR involves two half-reactions:the CO_(2) reduction half-reaction(CRHR)and the water oxidation half-reaction(WOHR).Generally,both half-reactions can be promoted by adjusting the wettability of catalysts.However,there is a contradiction in wettability requirements for the two half-reactions.Specifically,CRHR prefers a hydrophobic surface that can accumulate more CO_(2) molecules on the active sites,ensuring the appropriate ratio of gas-phase(CO_(2))to liquid-phase(H_(2)O)reactants.Conversely,the WOHR prefers a hydrophilic surface that can promote the departure of the gaseous product(O_(2))from the catalyst surface,preventing isolation between active sites and the reactant(H_(2)O).Here,we successfully reconciled the contradictory wettability requirements for the CRHR and WOHR by creating an alternately hydrophobic catalyst.This was achieved through a selectively hydrophobic modification method and a charge-transfer-control strategy.Consequently,the collaboratively promoted CRHR and WOHR led to a significantly enhanced OPCRR with a solar-to-fuel conversion efficiency of 0.186%.Notably,in ethanol production,the catalyst exhibited a 10.64-fold increase in generation rate(271.44μmol g^(-1)h~(-1))and a 4-fold increase in selectivity(55.77%)compared to the benchmark catalyst.This innovative approach holds great potential for application in universal overall reactions involving gas participation.

关键词： Hydrophobic Hydrophilic Gas transport Overall CO_(2)photoreduction Z-scheme

High-density triple-phase contact points for enhanced photocatalytic CO_(2) reduction to methanol

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Chinese Chemical Letters 2024年第2期35卷 252-256页

作者： Hanwen Jian Kaiming Deng Tongyu Wang Chengxi Huang Fang Wu Hailing Huo Bo Ouyang Xuan Liu Jingjing Ma erjun Kan Ang Li MIIT Key Laboratory of Semiconductor Microstructure and Quantum Sensing School of ScienceNanjing University of Science and TechnologyNanjing 210094China College of Information Science and Technology Nanjing Forestry UniversityNanjing 210037China State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering Ningxia UniversityYinchuan 750021China

The efficiency of photocatalytic CO_(2) reduction reaction(PCRR)is restricted by the low solubility and mobility of CO_(2) in water,poor CO_(2) adsorption capacity of catalyst,and competition with hydrogen evolution reaction(HER).Recently,hydrophobic modification of the catalyst surface has been proposed as a potential solution to induce the formation of triple-phase contact points(TPCPs)of CO_(2)(gas phase),H_(2) O(liquid phase),and catalysts(solid phase)near the surface of the catalyst,enabling direct delivery of highly concentrated CO_(2) molecules to the active reaction sites,resulting in higher CO_(2) and lower H+surface concentrations.The TPCPs thus act as the ideal reaction points with enhanced PCRR and suppressed HER.However,the initial synthesis of triple-phase photocatalysts tends to possess a lower bulk density of TPCPs due to the simple structure leading to limited active points and CO_(2) adsorption sites.Here,based on constructing a hydrophobic hierarchical porous TiO_(2)(o-HPT)with interconnected macropores and mesopores structure,we have significantly increased the density of TPCPs in a unit volume of the photocatalyst.Compared with hydrophobic macroporous TiO_(2)(o-MacPT)or mesoporous TiO_(2)(o-MesPT),the o-HPT with increased TPCP density leads to enhanced photoactivity,enabling a high methanol production rate with 1111.5μmol g^(−1) h^(−1) from PCRR.These results emphasize the significance of high-density TPCPs design and propose a potential path for developing efficient PCRR systems.

关键词： Photocatalysis CO_(2)reduction reaction Photocatalyst Triple-phase contact points Methanol

A small molecular electron acceptor based on asymmetric hexacyclic core of thieno[1,2-b]indaceno[5,6-b']thienothiophene for efficient fullerene-free polymer solar cells

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Science Bulletin 2018年第13期63卷 845-852页

作者： Wenchao Zhai Ailing Tang Bo Xiao Xiaochen Wang Fan Chen erjun zhou CAS Key Laboratory of Nanosystem and Hierarchical Fabrication CAS Center for Excellence in NanoscienceNational Center for Nanoscience and Technology College of Materials Science and Opto-Electronic Technology University of Chinese Academy of Sciences

A novel A-D-A(acceptor-donor-acceptor)type non-fullerene small molecule,A201,consisting of an asymmetric thieno[1,2-b]indaceno[5,6-b^0]thienothiophene(TITT)unit as middle D part and 2-(3-oxo-2,3-dihydroinden-1-ylidene)malononitrile(IC)groups as end-capped A parts was designed and synthesized.The asymmetric TITT building block showed a higher dipole moment of 0.85 Debye(1 Debye=3.33564?10^(à30)cm)compared with the symmetric analogues of indacenodithiophene(IDT)and indacenodithieno[3,2-b]thiophene(IDTT)of 0.098 and 0.13 Debye,respectively.The solution-processed bulk heterojunction solar cells using a benzotriazole(BTA)-based polymer of J71 as donor and A201 as acceptor,showed a power conversion efficiency(PCE)of 9.36%with an open-circuit voltage(V_(oc))of0.88 V,a short-circuit current(J_(sc))of 13.15 m A cm^(à2),and a fill factor(FF)of 0.67,under the illumination of AM 1.5G at 100 m W cm^(à2).The high PCE of this material combination could be attributed to its broad absorption spectrum and the high hole mobility(l_h)and electron mobility(l_e)of 9.56?10^(à4)and 5.17?10^(à4)cm^2V^(à1)s^(à1),respectively.These results indicate that the asymmetric electron-donating segments are promising to construct A-D-A type small molecular acceptors,which could largely enhance the diversity of building blocks to design photovoltaic materials.

关键词：太阳能电池不对称小分子聚合物电子免费 A201 变换效率

-1.2 V open-circuit voltage from organic solar cells

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Journal of Semiconductors 2021年第7期42卷 5-7页

作者： Ailing Tang Zuo Xiao Liming Ding erjun zhou Center for Excellence in Nanoscience(CAS) Key Laboratory of Nanosystem and Hierarchical Fabrication(CAS)National Center for Nanoscience and TechnologyBeijing 100190China Henan Institute of Advanced Technology Zhengzhou UniversityZhengzhou 450003China

Organic solar cells(OSCs)have achieved rapid advance due to the continuous development of high-performance key materials.Recently,the power conversion efficiencies(PCEs)of OSCs under 1 Sun condition(AM 1.5 G,100 mW/cm2)are striving toward 19%[1−5].The PCE improvement benefits from the largely enhanced short-circuit current density(Jsc)and fill factor(FF).However,these cells show relatively low open-circuit voltage(Voc)around 0.8-0.9 V.

关键词： materials. benefits solar

Gradually modulating the three parts of D-π-A type polymers for high-performance organic solar cells

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Journal of Energy Chemistry 2021年第11期30卷 532-537,I0012页

作者： Jialing zhou Peiqing Cong Lie Chen Bao Zhanga Yanfang Geng Ailing Tang erjun zhou CAS Key Laboratory of Nanosystem and Hierarchical Fabrication CAS Center for Excellence in NanoscienceNational Center for Nanoscience and TechnologyBeijing 100190China Center of Materials Science and Optoelectronics Engineering University of Chinese Academy of SciencesBeijing 100049China College of Chemistry Nanchang UniversityNanchang 330031China Henan Institutes of Advanced Technology Zhengzhou UniversityZhengzhou 450003China

Organic solar cells(OSCs)have received great attention for the prominent advantage of low-cost,light-weight and potential for fabricating flexible and semi-transparent device via roll-to-roll printing toward making be... 详细信息

关键词： Organic solar cells Non-fullerene acceptor Benzotriazole Side-chain strategy

PTB7-Th based organic solar cell with a high V_(oc) of 1.05 V by modulating the LUMO energy level of benzotriazole-containing non-fullerene acceptor

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Science Bulletin 2017年第18期62卷 1275-1282页

作者： Bo Xiao Yingjie Zhao Ailing Tang Haiqiao Wang Jing Yang erjun zhou CAS Key Laboratory of Nanosystem and Hierarchical Fabrication CAS Center for Excellence in Nanoscience National Center for Nanoscience and Technology Beijing 100190 China University of Chinese Academy of Sciences Beijing 100049 China State Key Laboratory of Organic-Inorganic Composite Beijing University of Chemical Technology Beijing 100029 China

The open-circuit voltage(V_(oc))of classical photovoltaic polymers,such as P3HT and PTB7-Th,are always restricted when combining with fullerene derivatives,due to the difficulty of modulating the energy levels of fullerene derivatives.Thus,design of new non-fullerene small molecule acceptor(NFSMA)is very significant to match with these mature polymer donors and improve the V_(oc)and power conversion efficiency(PCE).Here,a new benzotriazole(BTA)-based NFSMA,BTA7 was synthesized by adopting A_2@A_1ADAA_1@A_2type molecular backbone.By using a strong electron-accepting unit of malononitrile(M)as terminal segment A_2,BTA7 demonstrates strong crystallinity,red-shifted absorption spectrum and down-shifted lowest unoccupied molecular orbital(LUMO)energy levels in comparison with BTA_1and BTA_2.Organic solar cells(OSCs)based on PTB7-Th:BTA7 realized a high V_(oc)of 1.05 V with a moderate PCE of 4.60%.The energy loss(E_(loss)=E_gàe V_(oc))of 0.53 e V is lower than the experiential minimum value of0.6 e V,which indicates PTB7-Th still has large potential to improve the V_(oc)and photovoltaic performance after the development of novel electron acceptors.

关键词：富勒烯衍生物有机太阳能电池 LUMO能级电子受体 VOC 叔丁基甲苯苯并三唑功率转换效率

Wide Band Gap Non-Fullerene Small Molecular Acceptors Containing Spirobifluorene and Benzotriazole with Three Different End-Capped Groups for P3HT-Based Organic Solar Cells

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Chinese Journal of Chemistry 2018年第5期36卷 392-398页

作者： Xiaoyu Wen Bo Xiao Ailing Tang Junyi Hu Chunhe Yang erjun zhou Department of Chemistry School of Science Beijing Jiaotong University Beijing 100044 China CAS Key Laboratory of Nanosystem and Hierarchical Fabrication CAS Center for Excellence in Nanoscience National Center for Nanoscience and Technology Beijing 100190 China University of Chinese Academy of Sciences Beijing 200049 China

Spirofluorene （SF） and benzo[d][1,2,3]triazole （BTA） have been considered as promising building blocks to construct n-type photovoltaic materials. Herein, three new small molecule acceptors （SMAs） named BTA21, BTA23 and BTA27 with the structure of A2=A1-D-AI^A2 have been designed, in which SF and BTA were used as a central unit of D and bridged acceptor unit of A1, respectively. In addition, 3-ethylrhodanine, 2-（3-ethyl-4-oxothiazolidin-2-ylidene）malononitrile and malononitrile were chosen as terminal acceptor units to modulate the properties of the final SMAs. Three SMAs show wide optical band gaps （Eg） of 2.19, 2.15 and 2.22 eV, respectively, with gradually down-shift of the lowest unoccupied molecular orbital {LUMO） levels in the order of BTAZl, BTA23 and BTA27 depending on the electron-withdrawing capability of terminal acceptor units. BTA21 shows great advantages with respect to donor poly（3-hexylthiophene）（P3HT） over BTA23 and BTA27, such as well energy-level matching, complementary absorption and proper morpholgy, Concequently, P3HT：BTA21 shows the best power conversion efficiency （PCE） value of 3.28% with an open-circuit voltage （Voc） of 1.02 V, a short-circuit current （Jsc） of 5.45 mA.cm-2 and a fill factor （FF） of 0.59. These results indicate that the terminal acceptor group end-capped in SMAs plays a significant role in controlling their optical, electronic, and photovoltaic properties.

关键词： benzotriazole organic photovoltaic P3HT small molecular acceptor wide band gap

Gradual chlorination at different positions of D-π-A copolymers based on benzodithiophene and isoindigo for organic solar cells

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Materials Reports(Energy) 2021年第4期1卷 68-76页

作者： Jialing zhou Bao Zhang Yanfang Geng Qing Guo Qiang Guo erjun zhou CAS Key Laboratory of Nanosystem and Hierarchical Fabrication CAS Center for Excellence in NanoscienceNational Center for Nanoscience and TechnologyBeijing 100190PR China Center of Materials Science and Optoelectronics Engineering University of Chinese Academy of SciencesBeijing 100049PR China Henan Institute of Advanced Technology Zhengzhou UniversityZhengzhou 450001PR China

Isoindigo(IID)has been widely used as strong acceptor unit(A)to construct narrow bandgap polymers in organic field effect transistors(OFETs)and organic solar cells(OSCs).Combing with IID,we chose benzodithiophene(BDT)as the donor unit(D)and thieno[3,2-b]thiophene(TT)as theπbridge to construct a new type of D-π-A polymer PE70.Based on PE70,we adopt the chlorination strategy to fine-tune photoelectric characteristics and film morphology,and then developed PE74 and PE75.By blending with non-fullerene acceptor(NFA)Y6,device based on PE74 with chloride substitution on the BDT unit showed increasing photovoltaic performance.In addition,further chlorine substitution on the IID(PE75)would greatly reduce the non-radiative voltage loss(ΔV3),and the distorted molecular conformation also took responsible for the excessive recombination.As results,PE74:Y6-based device achieves a power conversion efficiency(PCE)of 11.06%with open-circuit voltage(VOC)of 0.76 V,which are higher than those of PE70:Y6(PCE of 10.40%and VOC of 0.72 V)and PE75:Y6-based device(PCE of 6.24%and VOC of 0.84 V).This work demonstrates the regularity of the photovoltaic performance caused by chlorination strategy in polymer in the non-fullerene OSC devices,which provide important insights into highperformance photovoltaic materials.

关键词： Isoindigo Polymer donor materials D-π-A polymer Chlorination strategy Non-fullerene acceptor Voltage loss