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The marriage of dual-acceptor strategy and C-H activation polymerization:naphthalene diimide-based n-type polymers with adjustable molar mass and decent performance

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Science China Chemistry 2023年第2期66卷 548-561页

作者： Ying-Han Zhao Wenhao Li Tao Shen Yan Zhao Yunqi Liu Yang Wang Laboratory of Molecular Materials and Devices Department of Materials ScienceFudan UniversityShanghai200438China Beijing National Laboratory for Molecular Sciences Key Laboratory of Organic SolidsInstitute of ChemistryChinese Academy of SciencesBeijing100190China

The development of readily accessible high-mobility n-type semiconducting polymers is in great demand for realizing highperformance p-n junction-based organic *** this study,we demonstrate that with the combination of dual-acceptor strategy and C-H direct arylation polymerization(DAr P),unipolar n-type semiconducting polymers can be conveniently *** tuning the monomer concentration,three dual-acceptor polymers,namely,poly(naphthalene diimide-alt-dithiophenyl pyrrolopyrrole-dione)(PNDI-DPP),poly(naphthalene diimide-alt-dithiophenyl isoindigo)(PNDI-IID),and poly(naphthalene diimide-alt-dithiophenyl bezothiadiazole)(PNDI-BT)can be obtained via C-H activation with decent number average molecular weight of~10 to 30 kg mol^(-1)and relatively narrow polydispersity index of~*** addition,these polymers are defect-free in nature as evidenced by the nuclear magnetic ***,we attribute the different molar masses of the three copolymers under the same DAr P condition to the differentα-C-H acidity,which may stem from different electronwithdrawing capability of the hydrogenated acceptor ***,the influence of the hydrogenated acceptor monomers on the optical,electrochemical and charge transporting properties is comprehensively *** the three dual-acceptor polymers,PNDI-BT demonstrates the highest electron mobilities of up to 0.6 cm^(2)V^(-1)s^(-1)in unipolar n-type organic transistors because of its relatively planar backbone,larger overlaps of the lowest unoccupied molecular orbital and strong *** that the transistor performance of PNDI-BT synthesized via C-H activation in this study is at least comparable to the one made by conventional C(sp^(2))-C(sp^(2))Stille or Suzuki cross-coupling *** study demonstrates the presented protocol can be a useful platform for sustainable and convenient synthesis of high-performance n-type semiconducting polymers.

关键词： n-type polymers C-H activation dual-acceptor strategy naphthalene diimide organic thin-film transistors

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Responsive Gels with the Polymer Containing Alternating naphthalene diimide and Fluorinated Alkyl Chains： Gel Formation and Responsiveness as Well as Electrical Conductivity of Polymer Thin Films

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Chinese Journal of Chemistry 2012年第7期30卷 1453-1458页

作者：罗河伟刘子桐蔡政旭吴刘锁张关心刘琛阳张德清 Beijing National Laboratory for Molecular Sciences Organic Solids LaboratoryInstitute of ChemistryChinese Academy of SciencesBeijing 100190China

A new electroactive polymer 1 with alternating NDI （naphthalene diimide） moieties and fluorinated alkyl chains was prepared and characterized. Gels of polymer 1 were formed in several solvents. Interestingly, gels of polymer 1 exhibited responsiveness toward N2H4, F and CN . Absorption and ESR spectroscopic studies revealed that such responsiveness is owing to the reduction of NDI moieties into the respective NDI＇-. In addition, thin films of polymer 1 were easily prepared with spin-coating technique and the electrical conductivity of thin films reached 52.4 S/m after exposure to NeH4 vapor.

关键词： responsive gels naphthalene diimide radical anion of naphthalene diimide electroactive polymer,electrical conductivity

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Synthesis and Characterization of Donor-Acceptor-Donor Triads Containing Tetrathiafulvalene and naphthalene diimide Units: Towards Regulation of the Intermolecular Charge-Transfer Interaction by Varying the Attached Side Groups

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Chinese Journal of Chemistry 2004年第3期22卷 296-305页

作者：郭雪峰张德清范清华朱道本 Center for Molecular Sciences Institute of Chemistry Chinese Academy of Sciences Beijing 100080 China Graduate School Chinese Academy of Sciences Beijing 100080 China

A series of donor-acceptor-donor triads 16 consisting of tetrathiafulvalene and naphthalene diimide units were synthesized and characterized. UV/Vis spectroscopic and cyclic voltammetric studies indicate that these triads show negligible intramolecular charge transfer interaction in the ground state. In contrast to that of the reference compound 36, their fluorescence intensities were reduced in the following sequences: 3≈4≈5≈6<1≈2, which is probably due to photoinduced electron transfer in triads 16. Two solid forms (yellow and green) of triads 15 were obtained, while only green form for triad 6 was obtained under the same conditions. Studies of the yellow and green forms with UV, XRD and DSC were performed. It was suggested that varying the attached side groups may regulate intermolecular charge transfer interactions in the solid state.

关键词： tetrathiafulvalene naphthalene diimide photoinduced electron transfer charge transfer interaction

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Synthesis, Characterization of Star-Shaped Analogue with Benzene Core and Three naphthalene diimide Side-Arms

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Chinese Journal of Chemistry 2017年第1期35卷 93-97页

作者： Linli Hu Jinling Li Jie Huang Jun Yin College of Chemistry and Environmental Engineering Yangtze University Jingzhou Hubei 434023 China School of Material Science & Engineering Henan University of Technology Zhengzhou Henan 450001 China Key Laboratory of Pesticide and Chemical Biology. Ministry of Education College of Chemistry Central China Normal University Wuhan Hubei 430079 China

Two star-shaped molecules with benzene core and three naphthalene diimide （NDI） side arms were facilely prepared by two-step imidization reaction from the 1,4,5,8-naphthalenetetracarboxylic dianhydride. Two com- pounds showed the similar UV-Vis absorption band as well as NDI. It was found that they displayed bathochromic shift of their UV-Vis absorption and emission spectra in film compared with that in solution, ascribing to the aggregation between molecules in the solid state. Reversible reduction process was observed by cyclic voltammetry and low lying LUMO energy levels （-3.83 eV for la, -3.87 eV for lb） were deduced, which suggest that these two compounds possessed good electron-acceptor property and can be used as potential n-type materials.

关键词： organic semiconductor electron-withdrawing naphthalene diimide

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n-Type Conjugated Polymer Based on Dicyanodistyrylbenzene and naphthalene diimide Units for All-Polymer Solar Cells

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Chinese Journal of Chemistry 2018年第5期36卷 406-410页

作者： Baitian He Qingwu Yin Jie Zhang Tao Jia Xiye Yang Xiao-Fang Jiang Fei Huang Yong Cao Institute of Polymer Optoelectronic Materials and Devices State Key Laboratory of Luminescent Materials and Devices South China University of Technology Guangzhou Guangdong 510640 China

All polymer solar cells （all-PSCs）, possessing superior mechanical strength and flexibility, offer the commercialization opportunity of the PSCs for flexible and portable devices. In this work, we designed and synthesized two copolymer acceptors based on dicyanodistyrylbenzene （DCB） and naph-thalene diimide （NDI） units. The corresponding copolymer acceptors are denoted as PDCB-NDI812 and PDCB-NDI1014. The medium band gap copolymer PBDB-T was selected as donor material for investigation of the photovoltaic performance. Two alI-PSCs devices showed power conversion efficiencies （PCE） of 4.26% and 3.43% for PDCB-NDI812 and PDCB-NDI1014, respectively. The improved PCE was ascribed to the higher short-circuit current （Jsc）, greater charge carrier mobility and higher exciton dissociation probability of the PBDB-T：PDCB-NDI812 blend film. These results suggest that DCB unit and NDI unit based copolymer acceptors are promising candidates for high performance alI-PSCs.

关键词： all polymer solar cells dicyanodistyrylbenzene naphthalene diimide alkyl chains

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Photoactive naphthalene diimide Functionalized Titanium-Oxo Clusters with High Photoelectrochemical Responses

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Journal of Donghua University(English Edition) 2023年第6期40卷 590-599页

作者：杨雨赵启新郑琦宣为民 College of Chemistry and Chemical Engineering Donghua UniversityShanghai 201620China College of Materials Science and Engineering Donghua UniversityShanghai 201620China State Key Laboratory for Modification of Chemical Fibers and Polymer Materials Donghua UniversityShanghai 201620China

Photoactive functionalized titanium-oxo clusters(TOCs)are regarded as an important model compound for dye-sensitized titanium dioxide solar ***,the dyes used for sensitizing TOCs are still ***,two cyclic TOCs are reported,namely,[Ti_(6)(μ_(3)-O)_(2)(Oi-Pr)_(8))(LA)_(2)]·i-PrOH(S1)and[Ti_(6)(μ_(3)-O)2(Oi-Pr)_(8))(LV)_(2)]·i-PrOH(S2),which are functionalized by photoactive naphthalene diimide(NDI)*** molecular structures and photophysical and photochemical properties were systematically *** shown by ultraviolet-visible(UV-vis)spectra and photocurrent study results,the band gap and the photocurrent response of S1 and S2 were derived from NDI ligands which extend the absorption edge of S1 and S2 approaching 500 nm and afford high photocurrent densities of 2.12μA/cm^(2)and 1.95μA/cm^(2)for S1 and S2,respectively,demonstrating the significance of the photoactive ligand in modulating photoresponse of *** work is expected to enrich the structural library of photoactive TOCs and provide insights into understanding the structure-property relationships of sensitized clusters.

关键词： titanium-oxo cluster naphthalene diimide photoactive photoelectrochemical response

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New Core-Expanded naphthalene diimides for n-Channel Organic Thin Film Transistors

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Chinese Journal of Chemistry 2013年第11期31卷 1428-1438页

作者： Yunbin Hu Xu Zhang Xiaodi Yang Hongxiang Li Xike Gao Laboratory of Materials Science Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China Laboratory of Advanced Materials Fudan University Shanghai 200433 China

Four classes of core-expanded naphthalene diimides （la, lb, 2a, 2b, 3 and 4） that bear different elec- tron-deficient sulfur heterocycles were designed and synthesized. The solution-processed thin films of la, 2a, 3 and 4 operated well in air as n-channel organic transistors with electron mobility ranging from MO 6 to 0.14 cm2/Vs, depending on the different conjugated backbones. The thin film microstructure studies were also carried out to un- derstand the variations of the electron mobility for thin films of la, 2a, 3 and 4.

关键词： naphthalene diimide sulfur heterocycle n-type organic semiconductor organic transistor

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Fine-tuning the molecular energy levels by incorporating thiophene units onto the π-backbone of core-expanded naphthalene diimides

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Chinese Chemical Letters 2016年第7期27卷 1022-1026页

作者： Dong Lu Xiao-Chun Yang Bing Leng Xiao-Di Yang Cong-Wu Ge Xue-Shun Jia Xi-Ke Gao Department of Chemistry College of Science Shanghai University Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Laboratory of Advanced Materials Fudan University

A series of core-expanded naphthalene diimides（NDI-DTYM） and thiophene-based derivatives（1a-c）were designed and synthesized to investigate the relationship between molecular structures and the highest occupied molecular orbital（HOMO） energy levels but has little impact on the lowest unoccupied molecular orbital（LUMO） energy *** results demonstrated that increasing the number of thiophene units can gradually elevate the HOMO energy levels but had little impact on the LUMO energy *** n-channel organic field-effect transistors（OFETs） based on 1b and 1c have demonstrated that these almost unchanged LUMO energy levels are proper to transport electrons.

关键词： naphthalene diimide Thiophene Molecular energy level Organic transistor Organic semiconductor

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Rylene diimide and Dithienocyanovinylene Copolymers for Polymer Solar Cells

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Chinese Journal of Polymer Science 2017年第2期35卷 230-238页

作者： Shui-xing Dai Shi-ming Zhang 凌启淡占肖卫 Fujian Key Laboratory of Polymer Materials College of Materials Science andEngineering Fujian Normal University Fuzhou 350007 China Department of Materials Science and Engineering College of Engineering Key Laboratory of Polymer Chemistry and Physics of Ministry of Education Peking University Beijing 100871 China Key Laboratory of Flexible Electronics & Institute of Advanced Materials Jiangsu National Synergetic Innovation Center for Advanced Materials Nanjing Tech University Nanjing 211816 China

Two polymers containing （E）-2,3-bis（thiophen-2-yl）acrylonitrile （CNTVT） as a donor unit, perylene diimide （PDI） or naphthalene diimide （NDI） as an acceptor unit, are synthesized by the Stille coupling copolymerization, and used as the electron acceptors in the solution-processed organic solar cells （OSCs）. Both polymers exhibit broad absorption in the region of 300-850 nm. The LUMO energy levels of the resulted polymers are ca. -3.93 eV and the HOMO energy levels are -5.97 and -5.83 eV. In the binary blend OSCs with PTB7-Th as a donor, PDI polymer yields the power conversion efficiency （PCE） of up to 1.74%, while NDI polymer yields PCE of up to 3.80%.

关键词： Perylene diimide naphthalene diimide Polymer solar cell Non-fullerene acceptor

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NDI-induced Topological Conversion of Human Telomeric G-Quadruplexes from Hybrid-2 to Parallel Form

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Chemical Research in Chinese Universities 2021年第3期37卷 795-800页

作者： HAO Xueyu LI Chunjie WANG Yu ZHANG Feng HOU Jingwei KANG Chunqing GAO Lianxun Laboratory of Polymer Composite and Engineering Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchun130022P.R.China University of Science and Technology of China Hefei230026P.R.China

G-Quadruplexes(GQs),which are formed by G-rich DNA sequences in human telomeres,have become an attractive target for cancer *** ligands to stabilize the conformation of human telomeric GQs in vivo are particularly important for structure-based ligand design and drug development targeting the noncanonical DNA *** we report the conformational conversion of Tel26 induced by a naphthalene diimide(NDI)ligand in K^(+)buffer,even at cellular physiological temperature(37℃)and under mimetic cellular crowding conditions created by Ficoll *** provide an insight into the dynamic conversion from initial hybrid-2 GQ topology to final parallel GQ *** results are helpful for the design of ligands with GQ conformation regulation.

关键词： G-Quadruplex naphthalene diimide Topological conversion Telomeric DNA

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