- Novel Electron Acceptors Bearing a Heteroquinonoid System. II. Synthesis and Conductive Complexes of 2,5-Bis(dicyanomethylene)-2,5-dihydrothienothiophene, 2,6-Bis(dicyanomethylene)-2,6-dihydrothienothiophene, and Their Derivatives
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Novel heteroquinoid compounds as potential electron acceptors, 2,5-bis(dicyanomethylene)-2,5-dihydrothienothiophene (4a), 3,6-dibromo derivative, 2,6-bis(dicyanomethylene)-2,6-dihydrothienothiophene, 3,5-dibromo derivative, and 4,4-dioxide were synthesized by the action of tetracyanoethylene oxide or by a Pd(0)-catalyzed substitution reaction with sodium dicyanomethanide on the corresponding α,α'-dihalo-substituted fused thiophenes.They show effectively diminished on-site Coulomb repulsion owing to the extensive conjugation, and most of their molecular complexes with various electron donors exhibit very high electrical conductivies up to metallic region.In addition, X-ray crystallographic analysis of the complex of 4a with bis(ethylenedithio)tetrathiafulvalene has elucidated that sulfur atoms embedded in 4a molecule are capable of inducing a significant intermolecular interaction, forming a sheet-like network structure.
- Yui, Koji,Ishida, Hideki,Aso, Yoshio,Otsubo, Tetsuo,Ogura, Fumio,et al.
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- Hexathienoacene: Synthesis, characterization, and thin-film transistors
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A new linear six thiophene-fused system of hexathienoacene (HTA) has been synthesized, which has also been compared with pentathienoacene (PTA) in terms of optical, electrochemical, and charge-transfer properties of organic semiconductors. The highest mobility of 0.06 cm2 V-1 s-1 with a current on/off ratio of 105 on n-octadecyltrichlorosilane (OTS)-treated SiO2/Si substrates has been achieved.
- Liu, Ying,Sun, Xiangnan,Di, Chong-An,Liu, Yunqi,Du, Chunyan,Lu, Kun,Ye, Shanghui,Yu, Gui
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- Tetrasubstituted Thieno[3,2- b]thiophenes as Hole-Transporting Materials for Perovskite Solar Cells
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Three hole-transporting materials (HTMs) were prepared following a straightforward synthetic route by cross-linking arylamine-based ligands with a simple thieno[3,2-b]thiophene (TbT) core. The novel HTMs were fully characterized with standard techniques t
- Urieta-Mora, Javier,García-Benito, Inés,Zimmermann, Iwan,Aragó, Juan,Molina-Ontoria, Agustín,Ortí, Enrique,Martín, Nazario,Nazeeruddin, Mohammad Khaja
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- Molecular design of benzothienobenzothiophene-cored columnar mesogens: Facile synthesis, mesomorphism, and charge carrier mobility
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Benzothienobenzothiophene (BTBT) liquid-crystalline semiconductors are arousing a lot of interest due to their long-range ordered, self-organizational abilities and high-charge carrier transport properties. In this work, we report the design and the straightforward synthesis of a homologous series of compounds containing the BTBT substructure by the successive Suzuki cross-coupling and FeCl3 oxidative Scholl cyclodehydrogenation reaction. Target π-conjugated aromatic, H-shaped sanidic mesogens self-organize into a classical hexagonal columnar mesophase over wide temperature ranges as deduced from polarized optical microscopy (POM), differential scanning calorimetry (DSC), and small-angle X-ray scattering (SAXS) investigations. UV/Vis absorption and photoluminescence spectra, measured in both solution and films, revealed strong photoluminescence with high quantum yields. The charge carrier mobility measured by the time-of-flight (TOF) technique showed a balanced ambipolar hole and electron mobility in the range of 10-3 cm2 V-1 s-1 between 100 and 230 °C in the mesophase. These BTBT-based columnar liquid crystals may represent attractive candidates to be incorporated within one-dimensional organic optoelectronic devices.
- Liu, Chun-Xia,Wang, Hu,Du, Jun-Qi,Zhao, Ke-Qing,Hu, Ping,Wang, Bi-Qin,Monobe, Hirosato,Heinrich, Beno?t,Donnio, Bertrand
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supporting information
p. 4471 - 4478
(2018/05/04)
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- Thiophene or furan derivative and organic light emitting device using the derivative
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The invention discloses a thiophene or furan derivative and an organic light emitting device using the derivative, and belongs to the technical field of organic optoelectronic materials. Thiophene and [3, 2-b] thiophene, furan and [3, 2-b] furan, or thiophene and [3, 2-b] thiophene 1, 1, 4, 4-tetroxide is adopted as a main structure in the derivative, the molecular weight of materials, pi conjugacy and eletrophilicity, charge transfer capacity, photochromism and the like can be adjusted by changing the linking method of a donor, meanwhile the problem that current carriers of a unipolar luminescent material are not balanced can be effectively solved, and thus the thiophene or furan derivative has high luminescence property, electronic transmission performance, membrane stability, thermostability and triplet state energy. The organic light emitting device prepared from the thiophene or furan derivative has the advantages of being excellent in electron chemistry performance and thermostability, long in service life and the like, and has a high luminescence efficiency even on the condition of a low starting voltage.
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Paragraph 0055; 0056; 0057
(2017/09/02)
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- Stereoscopic structure organic semiconductor material and monomer preparation method
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The invention discloses a stereoscopic structure organic semiconductor material and a monomer preparation method. The structural formula of monomer of the stereoscopic structure organic semiconductor material is shown in the instruction. The preparation method is simple, a butterfly monomeric compound is obtained and has four different polymerization sites, so that the compound polymerized at different sites can be obtained under different polymerization conditions, and different types of stereoscopic polymer organic semiconductor materials are obtained. Thiophene or EDOT (ethylenedioxy thiophene) derivatives are added to a mother nucleus, HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) energy levels of the material are further adjusted, the excellent organic semiconductor material is obtained, the preparation process is simple and convenient, product cost is greatly reduced, and a foundation is provided for application.
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Paragraph 0086
(2017/08/23)
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- BIS-THIENOBENZOTHIENOTHIOPHENE COMPOUNDS AND PROCESS FOR THEIR PREPARATION
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The present invention relates to bis-thienobenzothienothiophene compounds and a process for their preparation. More in particular, the present invention relates to a new angular bis-thienobenzothienothiophene compound and the process for its preparation wherein said process comprises reacting at least one dihalogenated dithiophene compound with at least one terminal alkyne and the subsequent double annulation reaction. Said bis-thienobenzothienothiophene compounds can be appropriately functionalized and polymerized to produce electron donor compounds that can be advantageously used in the construction of photovoltaic devices or semiconductor polymers. Furthermore, said bis-thienobenzothienothiophene compounds, after functionalization, may be advantageously used as spectral converters in luminescent solar concentrators.
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Page/Page column 21
(2016/07/05)
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- A new alkyl substituted and method for the synthesis of polythiophene
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The invention provides a method for replacing multi-thiophthene with beta-dialkyl in a synthesis formula I. The method comprises the following steps of: (f) reacting an intermediate in a formula 10 to obtain an intermediate in a formula 11; (g) reacting the intermediate in the formula 11 to obtain an intermediate in a formula 12; (h) reacting the intermediate in the formula 12 to obtain an intermediate in a formula 13; (i) reacting the intermediate in the formula 13 to obtain an intermediate in a formula 8; (j) reacting the intermediate in the formula 8 to obtain an intermediate in a formula 9; and (k) reacting the intermediate in the formula 9 to obtain a compound in a formula I. The invention further relates to the intermediate in the formula 9. The method disclosed by the invention is low in cost, simple in process, high in yield and low in pollution. The formulas 10, 11, 12, 13, 8 and 9 are shown in the description.
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- High-performance organic field-effect transistors based on single-crystalline microribbons of a two-dimensional fused heteroarene semiconductor
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A novel two-dimensional organic semiconductor material [1]benzothieno[3,2-b][1]benzothieno[2,1-b:3,4-b′:6,5-b″:7,8-b]tetra(benzothiophene) (BTBTTBT) which largely extends the scope of the π-conjugated framework of heteroarene through "H" configuration was synthesized and its thermal, optical and electrochemical properties were investigated. This 2D molecule enables the easy growth of single-crystalline microribbons by the physical vapor transport method, which were evidenced by XRD, SEM and TEM. The single-crystalline OFET devices were fabricated based on the individual BTBTTBT microribbon and the remarkable high mobility of 17.9 cm2 V-1 s-1 and on/off ratios of over 107 could be achieved.
- Wang, Yingfeng,Zou, Sufen,Gao, Jianhua,Zhang, Huarong,Lai, Guoqiao,Yang, Chengdong,Xie, Hui,Fang, Renren,Li, Hongxiang,Hu, Wenping
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p. 11961 - 11963
(2015/07/27)
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- Synthesis, crystal structure, and polymerization of butterfly-shaped thieno[3,2-b]thiophene oligomers
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A series of new butterfly-shaped thieno[3,2-b]thiophene oligomers with phenyl and thiophene units were synthesized through Suzuki coupling and Stille coupling reactions. The optical and thermal properties of these materials can be tuned by varying both su
- Liu, Ying,Liu, Qida,Zhang, Xingye,Ai, Ling,Wang, Yang,Peng, Ruixiang,Ge, Ziyi
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p. 1189 - 1194
(2013/06/27)
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- Versatile α,ω-disubstituted tetrathienoacene semiconductors for high performance organic thin-film transistors
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Facile one-pot [1 + 1 + 2] and [2 + 1 + 1] syntheses of thieno[3,2-b]thieno[2′,3′:4,5]thieno[2,3-d]thiophene (tetrathienoacene; TTA) semiconductors are described which enable the efficient realization of a new TTA-based series for organic thin-film transistors (OTFTs). For the perfluorophenyl end-functionalized derivative DFP-TTA, the molecular structure is determined by single-crystal X-ray diffraction. This material exhibits n-channel transport with a mobility as high as 0.30 cm 2V-1s-1 and a high on-off ratio of 1.8 × 107. Thus, DFP-TTA has one of the highest electron mobilities of any fused thiophene semiconductor yet discovered. For the phenyl-substituted analogue, DP-TTA, p-channel transport is observed with a mobility as high as 0.21 cm2V-1s-1. For the 2-benzothiazolyl (BS-) containing derivative, DBS-TTA, p-channel transport is still exhibited with a hole mobility close to 2 × 10-3 cm2V -1s-1. Within this family, carrier mobility magnitudes are strongly dependent on the semiconductor growth conditions and the gate dielectric surface treatment. Copyright
- Youn, Jangdae,Huang, Peng-Yi,Huang, Yu-Wen,Chen, Ming-Chou,Lin, Yu-Jou,Huang, Hui,Ortiz, Rocio Ponce,Stern, Charlotte,Chung, Ming-Che,Feng, Chieh-Yuan,Chen, Liang-Hsiang,Facchetti, Antonio,Marks, Tobin J.
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- Heteroacene compound, organic thin film including a heteroacene compound and electronic device including an organic thin film
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A heteroacene compound, an organic thin film including a heteroacene compound and an electronic device including a thin film are provided. The heteroacene compound is a compound having six rings fused together in a compact planar structure. The compound m
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(2009/03/07)
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- Poly(3,6-dimethoxy-thieno[3,2-b]thiophene): A possible alternative to poly(3,4-ethylenedioxythiophene) (PEDOT)
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Electropolymerization of the title compound leads to a conjugated polymer with redox potential, band gap, optical tranparency in the doped state and stability similar to those of PEDOT. The Royal Society of Chemistry 2005.
- Turbiez, Mathieu,Frere, Pierre,Leriche, Philippe,Mercier, Nicolas,Roncali, Jean
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p. 1161 - 1163
(2007/10/03)
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- Thienothiophenes. Part 2. Synthesis, metallation and bromine→lithium exchange reactions of thieno[3,2-b]thiophene and its polybromo derivatives
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Methods for the large-scale synthesis of thieno[3,2-b]thiophene [including a catalytic vapour-phase reaction (at 550°C) between 2-(2-thienyl)ethanol and carbon disulfide], its 2-carboxylic acid and its 3,6-dibromo and 2,3,5,6-tetrabromo derivatives are reported. With 2 mol equiv. of butyllithium thieno[3,2-6]thiophene gives its 2,5-dilithiated derivative and its 3,6-dibromo derivative gives the 3,6-dilithiated compound. By quenching with suitable electrophilic reagents these dilithiated compounds have been converted into various 2,5- or 3,6-disubstituted thieno[3,2-6]thiophenes, respectively. Likewise 2,3,5,6-tetrabromothieno[3,2-b]thiophene has been converted into 2,5-disubstituted 3,6-dibromothieno[3,2-b]thiophenes.
- Fuller, Lance S.,Iddon, Brian,Smith, Kevin A.
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p. 3465 - 3470
(2007/10/03)
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