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Halogenated thienoacene Derivatives with Improved Emission Properties

Chemical Research in Chinese Universities 2024年第4期40卷 699-703页

作者： ZHANG Jingmei MENG Zhihao ZHEN Yonggang HE Ping YU Panpan HU Wenping Advanced Innovation Center for Soft Matter Science and Engineering State Key Laboratory of Organic-Inorganic CompositesBeijing University of Chemical TechnologyBeijing100029P.R.China Wuhan National Laboratory for Optoelectronics Huazhong University of Science and TechnologyWuhan430074P.R.China State Key Laboratory of Fine Chemicals Dalian University of TechnologyDalian116024P.R.China Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province China West Normal UniversityNanchong637000P.R.China Key Laboratory of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education Jiangxi Normal UniversityNanchang330022P.R.China MOE Key Laboratory of Organic Integrated Circuits&Tianjin Key Laboratory of Molecular Optoelectronic Sciences Department of ChemistrySchool of SciencesTianjin UniversityTianjin300072P.R.China

thienoacenes is one of most important groups of semiconducting materials due to the high stability and superior ***,there are scarce studies on the emission properties of thienoacenes to ***,we synthesized fluorinated and chlorinated dibenzo[d,d’]thieno[3,2-b;4,5-b’]dithiophenes(DBTDTs)derivatives F6-DBTDT and Cl6-DBTDT by sulfoxide cyclization,significantly lowering the energy levels relative to the parent compound *** to single crystal structure analysis,F6-DBTDT molecules adopt one-dimensional slipped stacking with closeπ-πinteractions of 3.43Å(1Å=0.1 nm),which is different from the parent compound DBTDT with herringbone stacking ***,the halogenated DBTDT derivatives exhibit enhanced emission properties both in solution and in the solid state,opening up possiblities to improve photoluminescence of thienoacences by halogenation.

关键词： thienoacene Halogenation Photoluminescence Aggregation structure

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Acceptor-Donor-Acceptor Conjugated Oligomers Based on Diketopyrrolopyrrole and thienoacenes with Four, Five and Six Rings for Organic Thin-film Transistors

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Chinese Journal of Polymer Science 2017年第4期35卷 480-489页

作者： Qian Du Jing Shao Yao Gao Wei-li Li Hong-kun Tian Dong-hang Yan 耿延候 Fo-song Wang School of Material Science and Engineering and Collaborative Innovation Centre of Chemical Science and Engineering(Tianjin) Tianjin University The 46th Institute of the Sixth Academy of China Aerospace Science&Industry Corporation State Key Laboratory of Polymer Physics and Chemistry Changchun Institute of Applied ChemistryChinese Academy of Sciences

Three acceptor-donor-acceptor （A-D-A） conjugated oligomers, i.e., O1, 02 and 03, have been synthesized using diketopyrrolopyrrole （DPP） as an electron-acceptor unit, and naphtho[1,2-b：5,6-b＇]dithiophene （NDT）, anthra[1,2-b：5,6- b＇]dithiophene （ADT） or dithieno[3,2-b：Y,2＇-b＇]naphtbo[1,2-b：5,6-b＇]dithiophene （DTNDT） as electron-donor unit. These oligomers exhibit identical highest occupied molecular orbital （HOMO） and lowest unoccupied molecular orbital （LUMO） energy levels, which were ca. -5.1 and -3.3 eV, respectively. Upon thermal annealing, all three oligomers formed thin films with ordered microstructures, and their organic thin film transistors （OTFTs） exhibited p-type transport behavior. The mobility was increased with an extension of the size of D-units. 03 showed the best OTFT performance with the mobility of up to 0.20 cm2·V-1 ·s-1. The film quality of 03 was improved by adding 1 wt% poly（methylmethacrylate）（PMMA）. In consequence, the mobility of the O3-based devices was further enhanced to 0.30 cm2·V-1 ·s-1.

关键词： Diketopyrrolopyrrole (DPP) thienoacene Conjugated oligomers Organic thin-film transistors (OTFTs)

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Hexyl substitution of pentathienoacene toward a significant improvement in charge transport

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Chinese Chemical Letters 2019年第4期30卷 903-905页

作者： Ping He Hantang Zhang Chunhui Xu Yonggang Zhen Huanli Dong Wenping Hu Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province China West Normal University Beijing National Laboratory for Molecular Science Key Laboratory of Organic Solids Institute of Chemistry Chinese Academy of Sciences College of Chemistry and Material Science Shandong Agriculture University Tianjin Key Laboratory of Molecular Optoelectronic Sciences Department of Chemistry School of Science Tianjin University and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin)

A novel semiconductor, dihexyl-substituted pentathienoacene(C6-PTA) is designed and synthesized in five steps with the total yield up to 25.2%. The introduction of hexyl chains endow the thin film semiconductor with about threefold increase in carrier mobility and one to three orders of magnitude improvement in current on/off ratio. Furthermore, single crystal FETs based on C6-PTA exhibited mobility up to 0.64 cm^2 V^(-1) s^(-1), which is over 50 times higher than the thin film counterpart. The results indicate clearly that C6-PTA is a promising organic semiconductor with high stability.

关键词： Organic field-effect transistors Organic semiconductors thienoacene Charge transport Stability

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