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Synthesis of Long-Chain Oligomeric Donor and Acceptors via Direct Arylation for Organic Solar Cells

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Chinese Journal of Chemistry 2024年第5期42卷 523-532页

作者： Yu Wu Xin-Yu He Xu-Min Huang Ling-Jun Yang Peng Liu Na Chen Chang-Zhi Li Shi-Yong Liu Jiangxi Provincial Key Laboratory of Functional Molecular Materials Chemistry College of MaterialsMetallurgical and ChemistryJiangxi University of Science and TechnologyGanzhouJiangxi341000 China Department of Polymer Science and Engineering Zhejiang UniversityHangzhouZhejiang310027 China

The rapid synthesis of structurally complicated electron donors&acceptors still remains a major challenge in organic solar cells(OSC).In this work,we developed a highly efficient strategy to access long-chain oligomeric donor and acceptors for OSC applications.A series of cyclopentadithiophene(CPDT)and benzothiadiazole(BT)-basedπ-conjugated oligomers,i.e.,three oligomeric acceptors(BTDT)n-IC(n=1—3)and one long-chain oligomeric donor(BTDT)4-RD,are facilely synthesized by an atom-and step-economical,and labor-saving direct C—H arylation(DACH)reaction(i.e.,C—H/C—Br cross coupling).Note that(BTDT)4-RD involving five CPDT,four BT and two rhodamine(RD)building blocks is the longest oligomeric donor in the fullerene-free OSC devices ever reported.The dependence of the structure-property-performance correlation of(BTDT)n-IC(n=1—3)and(BTDT)4-RD on theπ-conjugation lengths is thoroughly investigated by opto-electrochemical measurements,bulk heterojunction(BHJ)OSC devices and microscopies.The(BTDT)1-IC:PBDB-T and(BTDT)4-RD:Y6 BHJs achieve power conversion efficiencies of 9.14%and 4.51%,respectively.Our findings demonstrate that DACH reaction is a powerful tool to tune the opto-electronic properties and device performances by regulating the lengths ofπ-conjugated oligomers with varied numbers of repeating units.

关键词： Long-chainπ-conjugated oligomer Organic solar cells Direct arylation Atom-economical synthesis Cyclopentadithiophene benzothiadiazole C—H activation Conjugation Oligomers

Structure-Property Relationship of Conjugated Polymers Utilizing Isomerized Fused benzothiadiazole-Based Building Blocks

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Chinese Journal of Chemistry 2023年第19期41卷 2525-2530页

作者： Jingyu Liu Wenhao Li Kaihu Xian Zhongwei Liu Yanru Li Xiang Yao Long Ye Yan Zhao Zhuping Fei Institute of Molecular Plus Department of ChemistryTianjin Key Laboratory of Molecular Optoelectronic ScienceTianjin UniversityTianjin300072 China Haihe Laboratory of Sustainable Chemical Transformations Tianjin300192 China Laboratory of Molecular Materials and Devices Department of Materials ScienceFudan UniversityShanghai200438 China School of Materials Science and Engineering Tianjin UniversityTianjin300072 China

Only a few fused benzothiadizole(BTz)based conjugated polymers have been applied in organic field-effect transistors(OFETs),and their performances were low,mainly due to the lack of available building blocks and in-depth study of the relationship between structure and performance.Herein,we report two isomeric fused BTz-based building blocks(M1 and M2)and their copolymers PBTzVBTz-T and PBTzVBTz-TT,PTVT-T and PTVT-TT.DFT study showed all polymers had nearly planar backbone geometries,and PBTzVBTz-TT exhibited the most linear backbone.PTVT-T and PTVT-TT exhibited red-shift absorption spectra and deeper LUMO level than those of PBTzVBTz-T and PBTzVBTz-TT.Thin film microstructure study demonstrated PBTzVBTz-TT and PTVT-TT had edge-on molecular orientation,while the others had the mixed molecular orientation of edge-on and face-on.Furthermore,PBTzVBTz-TT had the longest coherence length in thin film.All these features of PBTzVBTz-TT resulted in its highest carrier mobility of 0.1 cm^(2)·V^(–1)·s^(–1) among these polymers.

关键词： Conjugated polymers Organic field-effect transistors benzothiadiazole Isomerization Fused-ring systems

benzothiadiazole-based Conjugated Polymers for Organic Solar Cells

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Chinese Journal of Polymer Science 2021年第5期39卷 525-536,I0004页

作者： Chao Wang Feng Liu Qiao-Mei Chen Cheng-Yi Xiao Yong-Gang Wu Wei-Wei Li College of Chemistry and Environmental Science Hebei UniversityBaoding 071002China Beijing Advanced Innovation Center for Soft Matter Science and Engineering&State Key Laboratory of Organic-Inorganic Composites Beijing University of Chemical TechnologyBeijing 100029China

benzothiadiazole(BT)is an electron-deficient unit with fused aromatic core,which can be used to construct conjugated polymers for application in organic solar cells(OSCs).In the past twenty years,huge numbers of conjugated polymers based on BT unit have been developed,focusing on the backbone engineering(such as by using different copolymerized building blocks),side chain engineering(such as by using linear or branch side units),using heteroatoms(such as F,O and S atoms,and CN group),etc.These modifications enable BT-polymers to exhibit distinct absorption spectra(with onset varied from 600 nm to 1000 nm),different frontier energy levels and crystallinities.As a consequence,BT-polymers have gained much attention in recent years,and can be simultaneously used as electron donor and electron acceptor in OSCs,providing the power conversion efficiencies(PCEs)over 18%and 14%in non-fullerene and all-polymer OSCs.In this article,we provide an overview of BT-polymers for OSCs,from donor to acceptor,via selecting some typical BT-polymers in different periods.We hope that the summary in this article can invoke the interest to study the BT-polymers toward high performance OSCs,especially with thick active layers that can be potentially used in large-area devices.

关键词： benzothiadiazole Conjugated polymer Organic solar cells Electron donor Electron acceptor

Efficient solar cells based on cosensitizing porphyrin dyes containing a wrapped donor, a wrapped π-framework and a substituted benzothiadiazole unit

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Science China Chemistry 2019年第8期62卷 994-1000页

作者： Yunyue Lu Yingchun Cheng Chengjie Li Jiaxin Luo Weiqiang Tang Shuangliang Zhao Qingyun Liu Yongshu Xie Key Laboratory for Advanced Materials and Institute of Fine Chemicals School of Chemistry and Molecular Engineering East China University of Science and TechnologyShanghai 200237China School of Chemical Engineering and State Key Laboratory of Chemical Engineering East China University of Science and Technology Shanghai 200237China College of Chemical and Environmental Engineering Shandong University of Science and TechnologyQingdao 266510China

Three new porphyrin dyes XW45-XW47 have been synthesized employing a dialkoxy-wrapped phenothiazine donor, a tetraalkoxy-wrapped porphyrin π-framework, a benzothiadiazole(BTD)-based auxiliary acceptor, and an anchoring benzoic acid group. On the basis of our previously reported dye XW36, XW45 was synthesized by introducing a BTD unit to broaden the absorption spectrum, further introducing a hexyl-substituent into the BTD unit afforded XW46, and an additional fluorine atom was introduced to the carboxyphenyl acceptor to afford XW47. As expected, the BTD unit obviously broadens and red-shifts the absorption threshold of XW45-XW47 to ca.750 nm. Dye-sensitized solar cells(DSSCs) were fabricated based on a cobalt electrolyte using chenodeoxycholic acid(CDCA) as the coadsorbent. Under full sun illumination, XW45 exhibits an efficiency of 9.73%, which is slightly lower than that of 10.19% obtained for the reference dye SM315. By contrast, XW46 and XW47 show higher efficiencies than SM315 owing to the improved anti-aggregation ability associated with the hexyl group on the BTD unit and better ICT effect induced by the fluorine atom on the carboxyphenyl unit. Thus, XW47 exhibits the highest efficiency of 10.41% among the porphyrin dyes. Furthermore, PT-C6 was used as the cosensitizer to improve the light harvesting ability and efficiencies of the cells due to its broad absorption within 350–560 nm. Thus, high efficiencies of 10.32%, 11.38% and 10.90% were achieved for the cosensitized solar cells based on XW45–XW47, respectively, owing to the obviously enhanced photocurrent density(JSC). In addition, under 30% full sun illumination, XW46+PT-C6 exhibits a high efficiency of 13.08%. These results give an effective method for building high performance DSSCs through the cosensitization of porphyrin dyes containing a wrapped donor, a wrapped porphyrin framework and a properly substituted auxiliary benzothiadiazole unit.

关键词： dye-sensitized solar cells porphyrin dyes benzothiadiazole cosensitization

Foliar Application of benzothiadiazole and Salicylic Acid to Combat Sheath Blight Disease of Rice

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Rice science 2013年第5期20卷 349-355页

作者： Neerja SOOD B.S.SOHAL J.S.LORE Department of Biochemistry Punjab Agricultural UniversityLudhiana-141004 India Department of Plant Breeding and Genetics Punjab Agricultural UniversityLudhiana-141004 India

A field study was undertaken to ascertain the effects of elicitors viz. benzothiadiazole （BTH） and salicylic acid （SA） on defense related enzymes viz. peroxidase, phenylalanine ammonia lyase, superoxide dismutase, chitinase and 13-1,3-glucanase, and phenols in rice （Pusa Basmati I） plants. First foliar spray of BTH （50 mg/kg） and SA （50 mg/kg） was done at the maximum tillering stage and inoculation with Rhizoctonia solani was carried 24 h after elicitor treatment. Elicitors were further sprayed at every growth stage. Time course analysis showed peak accumulation of defense related enzymes and phenols in the rice leaves treated with BTH and SA, and accumulation was the highest at the flowering stage. Higher enzymatic activity was observed in elicitor treated plants inoculated with R. solani. Compared to the untreated control plants, application of elicitors before R. solani inoculation significantly elicited the defense related enzymes and phenols. Moreover, application of elicitors had a positive effect on yield and disease reduction. It is suggested that pretreatment of rice leaves with BTH and SA could be used to enhance the level of protection against sheath blight and to improve rice yield in the fields.

关键词： Oryza sativa benzothiadiazole salicylic acid defense related enzyme phenols sheath blight foliar application

A study on JA-and BTH-induced resistance of Rosa rugosa‘Plena’to powdery mildew(Sphaerotheca pannosa)

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Journal of Forestry Research 2018年第3期29卷 813-821页

作者： Junxin Yan Yanan Deng Jia Yu Yongqiang Zhang Defu Chi Northeast Forestry University Harbin 150040People’s Republic of China

Different concentrations of jasmonic acid(JA)and benzothiadiazole(BTH) were sprayed on 2-year-old Rosa rugosa‘Plena’ seedlings. The induced resistance of JA and BTH to Sphaerotheca pannosa(Wallr.) and the changes of their related physiological indices were investigated. Results showed that JA and BTH treatments had inhibitory impacts on S. pannosa infection. The optimal concentration of JA and BTH was 0.5 mmol/L for the disease-resistance induction of the leaves, its inductive effect was up to 66.36% for BTH and 54.49% for JA. Our results confirmed that exogenous JA and BTH significantly improved R. rugose ‘Plena’ resistance to S. pannosa. When treated with JA and BTH, activities of the three defense enzymes(POD, PPO, and PAL) increased significantly.Contents of total phenolics, flavonoids, and lignin also increased significantly. It is inferred from these results that exogenous JA and BTH could improve the resistance of R.rugose ‘Plena’ to S. pannosa through enhancing activities of the defensive enzymes and accumulation of secondary metabolites in the leaves.

关键词： benzothiadiazole Defensive enzyme Jasmonic acid Powdery mildew Sphaerotheca pannosa(Wallr.) Rosa rugosa ‘Plena’ Secondary metabolism

Vinyl-functionalized multicolor benzothiadiazoles: design,synthesis, crystal structures and mechanically-responsive performance

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Science China Chemistry 2019年第4期62卷 440-450页

作者： Jianhua Chen Fengying Ye Yan Lin Zhao Chen Shenghua Liu Jun Yin Key Laboratory of Pesticide and Chemical Biology Ministry of Education College of Chemistry Central China Normal University Department of Pharmacy Jiangxi University of Traditional Chinese Medicine Jiangxi Key Laboratory of Organic Chemistry Jiangxi Science and Technology Normal University

benzothiadiazole(BTD) has been extensively used as a building block in optical materials. In this work, a class of π-conjugated BTD-based luminogens BTD-685, BTD-580, BTD-675 and BTD-565 were designed by varying donor units and facilely synthesized by Heck coupling reaction. It was found that their emission in solid state covered the regio from orange, red to near infrared fluorescence. Investigation on photo-physical property manifested that they had strong solvatochromic behavior except symmetric 2-vinylpyridine substituted BTD-565. Crystal X-ray diffraction analysis revealed that they involved in multi weak intermolecular interactions. And loose molecular packing implied that they can be easily rearranged under external force stimuli.Indeed, all compounds showed reversible mechanically-responsive behavior in solid state. Interestingly, the vinylpyridinecontaining BTD-565 exhibited hypochromatic mechanochromic behavior, whereas others showed bathochromic mechanochromism behavior. It was worth mentioning that BTD-675 had self-recovery behavior after grinding. The powder X-ray diffraction study showed that these chromic processes may be mainly attributed to the reversible morphological changes between crystalline and amorphous phase upon grinding or fuming. These observations suggested that the vinyl-functionalized benzothiadiazoles can be considered as a type of excellent candidates in mechanically-responsive chromic materials.

关键词： benzothiadiazole mechanochromism multicolor aggregation

Synthesis and Photovoltaic Properties of Poly（5,6-bis（octyloxy）-4,7- di（thiophen-2-yl）benzo-[c] [l,2,5]-thiadiazole-9,9-dioctvlfluorene）

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Journal of Materials Science & Technology 2013年第12期29卷 1214-1218页

作者： Liwei Wang Feiyao Qing Yeping Sun Xiaoyu Li Haiqiao Wang State Key Laboratory of Organic-Inorganic Composites Key Laboratory of Carbon Fiber and Functional Polymers Ministry of Education College of Materials Science and Engineering Beijing University of Chemical Technology Beijing 100029 China

A donor-acceptor type conjugated polymer poly（5,6-bis（octyloxy）-4,7-di（thiophen-2-yl）benzo-[c] [1,2,5]- thiadiazole-9,9-dioctylfluorene）（POTBTF） based on octyloxy-containing benzothiadiazole （OTBT） and octyl- containing fluorine （F） was synthesized by Suzuki coupling reaction. The polymer possesses a narrow bandgap and strong light harvesting ability with excellent thermal stability and reasonable solubility. POTBTF exhibited a broad absorption from 300 to 600 nm with an absorption peak at 543.8 nm. The power conversion efficiency of the polymer solar cell based on POTBTF/PC71BM （1：3, w/w） reached 1.77% with a short-circuit current density of 6.69 mA/cm2, an open-circuit voltage of 0.71 V, and a fill factor of 0.374 under AM 1.5 G irradiation （100 mW/cm2） without annealing or any additives. The results indicate that introducing long alkoxy side chains into benzothiadiazole would not only improve the solubility of the polymers but also maintain the planarity of molecule conformation, and therefore, enhance the performance of photovoltaic devices.

关键词： Conjugated polymer Solar cell benzothiadiazole Fluorene

Effective design of A-D-A small molecules for high performance organic solar cells via F atom substitution and thiophene bridge

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Chinese Chemical Letters 2019年第12期30卷 2263-2265页

作者： Anwang He Yuancheng Qin Weili Dai Dan Zhou Jianping Zou Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle Nanchang Hangkong University

Three novel small molecules with acceptor-donor-acceptor(A-D-A) configuration,SBDT1,SBDT2 and SBDT3,where 4,8-bis(octyloxy)benzo[1,2-b:4,5-b’]dithiophene(BDT) as the electron-donating core connecting to thiophene-substituted benzothiadiazole(BT) as electron-withdrawing are reported.The effects of fluorine atoms on the photophysical properties by introducing different fluorine atoms into the benzothiadiazole unit were investigated.These SBDTs exhibit good thermal stability,excellent panchromatic absorption in solution and film.SBDT2 and SBDT3 with fluorine-substituted BT possess a relatively deeper the highest occupied molecular orbital(HOMO).These A-D-A type molecules were treated as donor and PC71 BM as acceptor in bulk heterojunction(BHJ) small-molecule organic solar cells(SMOSCs).Among them,device based on SBDT2 gave the best device performance with a PCE of 5.06%with Jsc of 10.56 mA/cm^2,Voc of 0.85 V,fill factor(FF) of 56.4%.These studies indicate that proper incorporation of fluorine atoms is an effective way to increase the efficiency of organic solar cells.

关键词： A-D-A small molecule benzothiadiazole Fluorination Organic solar cells