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We developed an efficient and direct method for synthesis of benzothiophene oxides from 1-bromo-2-[2-(trimethylsilyl)ethynyl]benzenes and thionyl chloride as an easily accessible source of the sulfinyl group. Benzothiophenes were also synthesized selectiv

A novel thienoacene-based conjugated oligomer, i.e.BTTT-T-C12, was designed and synthesized. Its highly asymmetric structural feature enables the preparation of two-dimensional single-crystalline thin films in millimetre size and ～100 nm thick by a solution processing method directly on the Si/SiO2 substrate. Single crystal organic thin film transistors exhibit a mobility of 0.70 cm2 V-1 s-1 and an on/off ratio of 5.7 × 104.

A new route to thiophene-ring-fused compounds with thionyl chloride as a sulfur source was developed. Use of an excess amount thionyl chloride directly gave the corresponding thiophene-ring-fused compound via further reduction of generated thiophene-S-oxide with excess thionyl chloride in some cases. One-pot reduction with tributylphosphine also gave thiophene-ring-fused compounds in good yields, and oxidation with NaClO·5H2O gave S-dioxides. In addition, one of the obtained thiazole-thiophene ring-fused compounds showed some unexpected mechanochromism behavior.

The present invention relates to a novel ligand compound, a transition metal compound and a catalyst composition comprising the same. The novel ligand compound and the transition metal compound of the present invention may be useful as a catalyst of polymerization reaction for preparing an olefin-based polymer having a low density.

A C—H sulfurated cyclization protocol starting from thioacetates is developed for straightforward construction of sulfur-containing benzoheterocyclics. The diversiform functional dihydrobenzothiophenes and thiochromans were comprehensively achieved through the Pd-catalyzed carbon- sulfur cyclization. Mechanistic studies indicated that C—H bond cleavage was involved in the rate-determining step. [1]Benzothieno-[3,2-b]- [1]benzothiophene (BTBT) and benzo[b]thieno[2,3-d]thiophene (BTT) were efficiently established as the well-known organic field-effect transistor (OFET) material molecules through this methodology.

The palladium-catalyzed oxidative preparation of dibenzothiophene derivatives from 2-biphenylyl disulfides by C?H functionalization is described herein. This procedure shows a high tolerance toward various functional groups and does not require the further addition of a metal oxidant, a base, or a ligand. Also, the present method was applied to the facile preparation of dibenzoselenophene.

Diaryliodonium salts are characterized by poor atom economy with the formation of one equivalent of an iodoarene as waste. We have developed an atom-economic iron-catalyzed protocol for the synthesis of a variety of thioethers with diaryliodonium salts. Not only cyclic diaryliodonium salts but also linear diaryliodonium salts were found to perform well in the reactions.

PROBLEM TO BE SOLVED: To provide an industrially available method of producing a heteroacene compound through a chlorinated aromatic compound. SOLUTION: The present invention provides a method for producing a heteroacene compound by the reaction of a chlorinated aromatic compound with 1,8-diazabicyclo [5.4.0]undeca-7-ene (DBU) and/or 1,5-diazabicyclo [4.3.0]nona-5-ene (DBN) in the presence of transition metal catalyst and organic solvent. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Much interest has been paid to cyclic diaryliodonium salts as bis(electrophile)s in transition-metal-catalyzed annulation reactions to produce polycyclic (hetero)aromatic hydrocarbons. Herein, we report that dibenziodolium triflates smoothly react with potassium thioacetate in the presence of CuCl2in THF or DMSO at 100–110 °C to afford the corresponding dibenzothiophenes in good-to-high yields. The coupling reaction tolerates reactive functional groups such as chloro and cyano and serves as a facile and reliable method for the synthesis of unsymmetrical dibenzothiophenes.

A novel series of air-stable and highly extended π-conjugated naphtho[2,1-b:3,4-b′]bisthieno[3,2-b][1]benzothiophene derivatives, NBTBT-n (n = 6, 8, 10, and 12) and NBTBTF-10, was developed. The influence of various alkoxy-side groups including straight chain with different chain lengths and branched chain on the FET device performance was also investigated. There was a progressive enhancement in the NBTBT-based OFET device performance with an increase in the annealing temperature. The OFET devices based on NBTBT-10 fabricated by vacuum deposition exhibited the best performance with a hole mobility of 0.25 cm2 V-1 s-1 and an on/off ratio of 105-106 after annealing at 220 °C. In addition, fluorinated naphtho[2,1-b:3,4-b′]bisthieno[3,2-b][1]benzothiophene, NBTBTF-10, showed good p-type transistor behaviour with a hole mobility of 0.24 cm2 V-1 s-1 and an on/off ratio of 106-107 which was achieved at a lower annealing temperature of 140 °C, suggesting the important contribution of the dipole-dipole interactions induced by the fluorine atoms in the molecular packing. As a result, the naphtho[2,1-b:3,4-b′]bisthieno[3,2-b][1]benzothiophene framework shows promise as a useful building block to construct organic semiconductors for next-generation high performance organic electronics.

In one embodiment, provided are a new class of diarylethene-containing photochromic compounds with the incorporation of silicon-or phosphorus-containing heterocycles into the "ethene" part of the diarylethene backbone that has been shown to be capable of displaying tunable, robust and thermally stable photochromic properties. Also provided are methods for synthesizing these compounds, as well as uses of these compounds as these compounds may be used as the photochromic layer in an optical recording material and other optical functioning devices.

Three new benzothieno[3,2-b]thiophene (BTT; 1) derivatives, which were end-functionalized with phenyl (BTT-P; 2), benzothiophenyl (BTT-BT; 3), and benzothieno[3,2-b]thiophenyl groups (BBTT; 4; dimer of 1), were synthesized and characterized in organic thin-film transistors (OTFTs). A new and improved synthetic method for BTTs was developed, which enabled the efficient realization of new BTT-based semiconductors. The crystal structure of BBTT was determined by single-crystal X-ray diffraction. Within this family, BBTT, which had the largest conjugation of the BTT derivatives in this study, exhibited the highest p-channel characteristic, with a carrier mobility as high as 0.22 cm2 V-1 s-1 and a current on/off ratio of 1×10 7, as well as good ambient stability for bottom-contact/bottom-gate OTFT devices. The device characteristics were correlated with the film morphologies and microstructures of the corresponding compounds. Copyright

A series of the title ylides was prepared by reaction of fused thiophene and selenophene derivatives with di-tert-butyl diazomalonate. Their thermal stability depended highly on their structure. While the terminal thiophenium-and selenophenium-ylides smoo

The novel heterocyclic fulgide, 3-(1-methylethylidene)-4-[1-(2- methylthieno[3,2-b]-[1]benzothiophen-3-yl)ethylidene]dihydrofuran-2,5-dione, was obtained and isolated as a Z-isomer. Its structure was confirmed by electronic absorption spectroscopy, 1H NMR spectroscopy, and X-ray diffraction analysis. The novel thienothiophene fulgide is photochromic in both solutions and the crystalline state. Its colored cyclic form resists photodegradation and is thermally stable. When benzothiophene is annulated with the thienyl fragment, the long-wavelength absorption peak of the cyclic isomer of the novel fulgide experiences a bathochromic shift compared to the earlier described 3-thienylfulgide. The TD B3LYP/6-311G**-calculated spectroscopic characteristics of the fulgide isomers suggest the formation of their photostationary mixture under irradiation with λ = 365 nm.

New conducting polymers, including poly[thieno[3,2-b][1]benzothiophene] (poly-TBT) and poly [6-methoxythieno[3,2-b][1]benzothiophene] (poly-MeOTBT) were electrosynthesized by anodic oxidation of the corresponding monomers in 0.1 M LiClO4 acetonitrile solution. Poly-TBT and poly-MeOTBT electroactive films were formed on platinum electrodes and characterized spectroscopically. FT-IR studies show that both polymers present couplings occurring on the thiophene moiety and the phenyl ring, with a step-like structure. MALDI-TOF mass spectrometry indicates that poly-TBT and poly-MeOTBT films are mainly constituted of short-chain oligomers. The results of molecular orbital (MO) calculations performed on the basis of a radical-cation electropolymerization mechanism are in good agreement with our spectral data.

Various thieno[3,2-c] anellated (5a, 26) and dithieno[3,2-c:2,3-e] anellated 1,2-dithiins (32 a-c, 45) were obtained starting from appropriate thiophene precursors. The absorption maxima covered the range from 430 to 467 nm indicating olefinic rather than aromatic character of the anellating thiophene units. Access to the isomeric thieno[2,3-c] anellated series failed due to competing reactions in the final stage, e.g. by the formation of the 12-membered cyclic bis-disulfide 53.