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Fully conjugated Covalent Organic Frameworks:Synthesis,Structures and Applications

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Chinese Journal of Chemistry 2023年第23期41卷 3447-3472页

作者： Yueshuai Xu Guanshi Ren Dianqi Zhang Lishui Sun Yingjie Zhao College of Polymer Science and Engineering Qingdao University of Science and TechnologyQingdaoShandong266000 China

This review presents a comprehensive examination of fully conjugated covalent organic frameworks(COFs),which constitute an emerging class of porous materials with immense potential for diverse *** article focuses on diversified fully conjugated COFs,including sp2 carbon-carbon linkages,pyrazine linkages,benzobisoxazole linkages,dioxin linkages,β-aminoalkenone linkages,*** synthesis techniques and structural attributes of these COFs are expounded upon in great detail,along with their potential applications in various *** review thus provides a valuable resource for researchers keen on delving into the synthesis and applications of fully conjugated COFs,thereby highlighting their potential for developing novel functional materials with distinctive properties.

关键词： Covalent organic frameworks Fully-conjugated system Crystallinity Stability Conjugation Porous polymers conjugated polymers

A Novel Thiophene Derivative-based conjugated Polymer for Polymer Solar Cells with High Open-circuit Voltage

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Chinese Journal of Chemistry 2012年第9期30卷 2219-2224页

作者：谌烈沈星星陈义旺 Department of Chemistry/Institute of polymers Nanchang UniversityNanchangJiangxi 330031China Jiangxi Key Laboratory for New Energy Chemistry Nanchang UniversityNanchangJiangxi 330031China

A novel D-A alternative conjugated polymer PBDTDMCT containing benzo[1,2-b：4,5-b＇]dithiophene （BDT） and dimethyl thiophene-3,4-dicarboxylate （DMCT）, was designed and synthesized by Stille cross-coupling reaction. The copolymer exhibited excellent solubility and good thermal stability. The optical band gap determined from the onset of absorption of the polymer film was 2.10 eV. By incorporation of the ester groups into the polymer side chain, the HOMO level of polymer PBDTDMT was tuned to be deep-lying （--5.65 eV）. Open-circuit voltage of polymer solar cells constructed based on PBDTDMT and [6,6]-phenyl-CTwbutyric acid methyl ester （PCTIBM） can be tuned to achieve values as high as ca. 1.0 V.

关键词： conjugated polymers HOMO energy level polymer solar cells open-circuit voltage

Synthesis and characterization of red-emission PPV copolymers containing fluorenone unit

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Journal of Central South University 2010年第2期17卷 269-276页

作者：邹应萍潘春跃张振华刘波贺跃辉周科朝周祎李永舫 School of Chemistry and Chemical Engineering Central South University State Key Laboratory of Powder Metallurgy Central South University Key Laboratory of Organic Solids Institute of ChemistryChinese Academy of Sciences

Two soluble copolymers of fluorenone and dioctoxylbenzene （PFN） or anthracene （PFNAn） were synthesized through Heck polymerization, and were characterized by gel permeation chromatography （GPC）, FT-IR, IH-NMR, elemental analysis and thermogravimetric analysis. The polymers possess good solubility in common organic solvents and high thermal stability with the Onset decomposition temperature at higher than 410 ℃. The photophysical properties of the polymers were investigated in both solutions and spin-coated films. Cyclic voltammetry results revealed that the copolymers possess higher electron affinity and reversible reduction/re-oxidation processes. Their electroluminescent properties were further investigated. PFN and PFNAn show stable and saturated red light emission with high thermal stability and high electron injection ability. This type of conjugated polymers may be promising for the applications as electron acceptors in polymer photovoltaic cells and electron transporting materials.

关键词： conjugated polymers fluorenone photophysical properties red-emission polymers electron affinity

Two-dimensional like conjugated copolymers for high efficiency bulk-heterojunction solar cell application:Band gap and energy level engineering

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Science China Chemistry 2011年第4期54卷 685-694页

作者： DUAN ChunHui WANG ChuanDao LIU ShengJian HUANG Fei CHOY C.H.Wallace CAO Yong Institute of Polymer Optoelectronic Materials & Devices Key Laboratory of Specially Functional Materials of the Ministry of Education South China University of Technology Guangzhou 510640China Department of Electrical and Electronic Engineering The University of Hong KongPokfulam RoadHong KongChina

Three two-dimensional like conjugated copolymers PFSDCN,PFSDTA and PFSDCNIO,which consist of alternating fluorene and triphenylamine main chain,and different pendant acceptor groups (malononitrile,1,3-diethtyl-2-thiobarbituric acid and 2-(1,2-dihydro-1-oxoinden-3-ylidene)malononitrile) with thiophene as π-bridge,have been designed,synthesized and *** structure-property relationships of the two-dimensional like conjugated copolymers were systematically *** absorption spectra,band gaps,and energy levels of the polymers were effectively tuned by simply attaching different acceptor *** the electron-withdrawing ability of the acceptors increased,the band gaps of the polymers were narrowed from 2.05 to 1.61 eV;meanwhile,the LUMO energy levels of the polymers decreased from -3.27 to -3.75 eV,whereas their relatively deep HOMO energy levels of ～-5.35 eV were *** solar cells were fabricated and characterized by using the three polymers as donor materials and the highest power conversion efficiency of 2.87% was achieved for the device based on PFSDTA:(6,6)-phenyl-C71-butyric acid methyl ester blend.

关键词： conjugated polymers two-dimensional like polymers band gaps bulk-heterojunction solar cells

Donor-Acceptor Oligomers and polymers Composed of Benzothiadiazole and 3-Hexylthiophene： Effect of Chain Length and Regioregularity

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Chinese Journal of Chemistry 2013年第11期31卷 1367-1379页

作者： Jintu Wang Huaiying Ye Hongjiao Li Chongyu Mei Jun Ling Weishi Li Zhiquan Shen Laboratory of Organic Functional Materials and Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China Department of Polymer Science and Engineering Zhejiang University Hangzhou Zhejiang 310027 China

A series of donor-acceptor oligomer OBTThn （n = 1- 7） and polymer PBTThl and PBTTh2 composed of al- ternative 2,1,3-benzothiadiazole and 3-hexylthiophene have been designed and synthesized for the purpose of in- vestigation on the effect of chain length and side-chain regioregularity on their basic properties and photovoltaic performance. In the OBTThn oligomers and PBTThl polymer, all the hexyl side chains on thienyl units orient to- ward the same direction. Upon elongation of the chain length, the intramolecular charge transfer （ICT） absorption band in solution gradually redshifts from 398 nm for OBTThl to 505 nm for OBTThT, then to 512 nm for PBTThl polymer. Meanwhile, the HOMO energy level increases from -5.45 eV （OBTTh0 to -5.08 eV （OBTThT） and -5.09 eV （PBTThl）, and the LUMO energy level decreases from -3.11 eV （OBTTh0 to -3.30 eV （OBTThT） and -3.33 eV （PBTThl）, thus giving a smaller and smaller energy bandgap for higher oligomers and polymers. Theo- retical calculation suggests straight line-like backbone geometry for this series of oligomers and polymer. On the other hand, polymer PBTTh2 possesses a different side-chain regioregularity, in which every two neighbor hexyl side chains are arranged in different orienting direction. It is theoretically suggested to have curved line-like back- bone geometry. In solution, it shows similar photophysical and electrochemical properties as PBTThl. However in film state, it displays a less redshift in the ICT band as refer to that in solution than PBTThl. In combination with [6,6]-phenyl-C61-butyric acid methyl ester （PC61BM）, these oligomers and polymers were used as donor material to fabricate organic bulk heterojunction solar cells. Again, chain length-dependent device photovoltaic performance was observed. The device based on OBTTh4 showed a power conversion efficiency of 0.16%, while it increased to 0.36% and 0.49% for the devices based on OBTTh6 and PBTThb respectively. However, the side-chain regio- regularity ha

关键词： conjugated polymers organic solar cells regioregularity donor-acceptor oligomers

Tetramethylammonium Iodide Additive for Enhancing the Charge Carrier Mobilities of Diketopyrrolopyrrole-Based Conju-gated Polymer in Ambipolar Organic Field-Effect Transistors

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Chinese Journal of Chemistry 2023年第9期41卷 1028-1036页

作者： Waner He Qian Liu Sultan Otep Hidetoshi Matsumoto Sergei Manzhos Prashant Sonar Aung Ko Ko Kyaw Tsuyoshi Michinobu Department of Materials Science and Engineering Tokyo Institute of TechnologyTokyo 152-8552Japan Guangdong University Key Laboratory for Advanced Quantum Dot Displays Department of Electrical and Electronic EngineeringSouthern University of Science and TechnologyShenzhenGuangdong 518055China Center for Materials Science School of Chemistry and PhysicsFaculty of ScienceQueensland University of TechnologyBrisbaneQLD 4000Australia School of Materials and Chemical Technology Tokyo Institute of TechnologyTokyo 152-8552Japan

Diketopyrrolopyrrole(DPP)is one of the most promising building blocks for constructing polymer semiconductors with high charge-carrier mobilities in organic field-effect transistors(OFETs).In this study,a novel DPP-based conjugated polymer,PDPPy-BDD,was designed and *** ambipolar field-effect transistor characteristics were realized with the average hole and electron mobilities of 3.5×10^(-3)and 3.07×10^(-2)cm^(2)V^(-1)s^(-1),*** the hole and electron mobilities could be successfully en-hanced by using a tetramethylammonium iodide(NMe4l)*** an enhancement was attributed to the formation of stronger interchainπ-πstackings,the weakening of the face-on packing orientation in the thin film state,and the higher channel conductivi-ties in the OFETs.

关键词： Diketopyrrolopyrrole Pyridine Charge transport conjugated polymers Organic field-effect transistors Semiconductors Tetramethylammonium iodide Thin films

Direct Arylation Polycondensation of Thiophene-Based C−H Monomers

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Chinese Journal of Chemistry 2023年第21期41卷 2908-2924页

作者： Xuwen Zhang Yibo Shi Yunfeng Deng Yanhou Geng School of Materials Science and Engineering and Tianjin Key Laboratory of Molecular Optoelectronic Science Tianjin Universityand Collaborative Innovation Center of Chemical Science and Engineering(Tianjin)Tianjin300072 China Joint School of National University of Singapore and Tianjin University International Campus of Tianjin UniversityBinhai New CityFuzhouFujian350207 China

Direct arylation polycondensation(DArP)has emerged as an eco-friendly and atom-efficient methodology for the syntheses ofπ-conjugated polymers(CPs).This approach features the direct C—H arylation of an aromatic hydrocarbon with an aryl *** the prevalence of thiophene-containing CPs,achieving efficient and defect-free DArP of thiophene-based C−H monomers is of great *** review presents a mechanistic insight into DArP and describes the development of DArP catalytic systems for varied thiophene-based C−H ***,the control of the primary defects(i.e.,branching and homo-coupling)in thiophene-based DArP is also *** emphasizing the principles behind monomer selection and catalytic system optimization,this review intends to provide a framework for future advancements in the DArP of thiophene-containing CPs.

关键词： conjugated polymers Direct arylation polycondensation Sustainable chemistry Catalytic system Thiophene

Ladder-type Diindenopyrazine Based conjugated Copolymers for Organic Solar Cells with High Open-circuit Voltages

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Chinese Journal of Chemistry 2013年第11期31卷 1409-1417页

作者： Shanci Chen Changquan Tang Zhigang Yin Yunlong Ma Dongdong Cai Dhanavel Ganeshan Qingdong Zheng State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of Matter Chinese Academy of Sciences Fuzhou Fujian 350002 China

A ladder-type diindenopyrazine （IPY） was synthesized and used as a building block for constructing conjugated copolymers. Three copolymers based on the IPY moiety were obtained via the Suzuki coupling reaction with dif- ferent monomers, including 4,7-dithien-2-yl-2,1,3-benzothiadiazole （DBT）, 5,8-dithien-2-yl-2,3-diphenylquinoxa- line （DTQ）, and 5,8-dithien-2-yl-2,3-di（4-fluorophenyl）quinoxaline （DFTQ）. The obtained polymers were charac- terized by 1H NMR spectroscopy, UV-Vis absorption spectroscopy, cyclic voltammetry, and gel permeation chro- matography （GPC）. Owing to the four solubilizing alkyl chains on the IPY unit, all the three copolymers have good solubility in common solvents. These polymers have deep-lying HOMO energy levels in the range of-5.55-5.60 eV, and exhibit field-effect mobilities as high as 0.006 cm2.V-l.s i. Photovoltaic applications of these polymers as light-harvesting and hole-conducting materials were investigated in conjunction with [6,6]-phenyl-C6rbutyric acid methyl ester （PC61BM）. Both conventional and inverted devices were fabricated based on these three polymers. A power conversion efficiency （PCE） of 2.53% and a high open-circuit voltage of 1.00 V were obtained under simu- lated solar light AM 1.5 G （100 mW/cm2） from an inverted solar cell with an active layer containing 25 wt% lad- der-type IPY containing copolymer （PIPYDTQ） and 75 wt% PC61BM. Moreover, a high open-circuit voltage of 1.02 V and a PCE of 2.40% were achieved from a conventional solar cell based on PIPYDTQ.

关键词： conjugated polymers diindenopyrazine organic solar cells field-effect transistors open-circuit volt-age

New materials based on carbazole for optoelectronic device applications:Theoretical investigation

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Chinese Chemical Letters 2008年第4期19卷 488-492页

作者： K.Hasnaoui H.Zgou M.Hamidi M.Bouachrine Unité de Recherche sur les Macromolécules et Modélisation Faculté des Sciences et TechniquesB.P.509 Boutalamine5200 ErrachidiaMorocco Unité de Chimie Théorique AppiquéeFaculté des Sciences et TechniquesB.P.509 Boutalamine5200 ErrachidiaMorocco Unité de Chimie Théorique Appliquée Faculté des Sciences et TechniquesB.P.509 Boutalamine5200 ErrachidiaMorocco Unité de Recherche sur les Macromolécules et Modélisation Faculté des Sciences et TechniquesB.P.509 Boutalamine5200 ErrachidiaMorocco

A quantum-chemical investigation on the structural and optoelectronic properties of two materials based on carbazole is carried *** purpose is to display the effect of grafting the fluorine atoms on their optoelectronic and physico-chemical *** addition to solubility in the polar solvents and the modification in geometric parameters,the substitution of fluorine destabilizes the HOMO and LUMO levels,decreases the band gap energy and raises conjugation *** properties suggest the substituted fluorine compound as a good candidate for optoelectronic applications.

关键词： conjugated polymers DFT theoretical investigation Carbazole Optoelectronic applications