- The efficient synthesis of dithieno [3,4-b:3',4'-d] thiophene
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The efficient synthesis of dithieno[3,4-b:3',4'-d]thiophene was improved by the introduction of TMS groups in four synthetic steps including TMS protection, sulfidation, intramolecular cyclization, and TMS removal. The total yield is 55-63% with 3,4-dibro
- Xu, Li,Wang, Zhen,Xu, Kun,Shi, Jianwu,Wang, Hua
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- Synthesis, polymerization and characterization of substituted dithieno [3,4-b: 3',4'-d] thiophenes
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Chemical or electrochemical oxidation of substituted dithieno [3,4- b:3',4'-d]thiophenes provides polymers with defined regiochemical structures. These materials have lower bandgaps (0.7-0.9 eV) than the unsubstituted fused heteroarene. Potential cycling of the 1,3-dimethyl substituted polymer film shows repetitive p- and n-dopability. The chemically-prepared dioctyl analog is soluble in common solvents such as chloroform, dichloromethane and THF. However, overoxidation of the polymers at an electrode surface presents a limitation to the polymerization of substituted analogs of the parent fused heteroarene.
- Inaoka, Seiji,Collard, David M.
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- Synthesis of dithienothiophenes, cyclopentadithiophene and silacyclopentadithiophenes using palladium catalyzed cyclization
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The intramolecular cyclization of bromothiophene derivatives with hexamethylditin in the presence of tetrakis(triphenylphosphine)palladium(O) gave dithienothiophenes, cyclopentadithiophene, and silacyclopentadithiophenes in moderate to good yields.
- Iyoda, Masahiko,Miura, Mami,Sasaki, Shigeru,Kabir, S. M. Humayun,Kuwatani, Yoshiyuki,Yoshida, Masato
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- Asymmetric b thiopheneglyoxylic and fragrant heterocyclic the synthetic method of the compound of
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The invention discloses a synthesis method of asymmetrical beta-bromodithieno heteroaromatic compounds, which comprises the following steps: reacting 4,4'-dibromo-3,3'-bithiophene used as a raw material and n-butyl lithium in anhydrous ethyl ether; then performing cyclization reaction under the action of different cyclization reagents (bis(benzenesulfonyl)thioether, N,N-dimethylformyl chloride and dimethyl dichlorosilane); and finally, performing water quenching to generate the asymmetrical beta-bromodithieno heteroaromatic compounds and symmetrical dithieno heteroaromatic compounds, wherein the asymmetrical beta-bromodithieno heteroaromatic compounds and a small amount of symmetrical dithieno heteroaromatic compounds are selectively obtained at a high yield in the presence of the n-butyl lithium; the asymmetrical beta-bromodithieno heteroaromatic compounds include 3-bromo-dithieno[2,3-b:3',4'-d]thiophene, 3-bromo-7H-cyclopentano[1,2-b:3,4-c']dithiophene-7-one and 3-bromo-7,7-dimethyl-7H-dithieno[2,3-b:3',4'-d]silole; and the symmetrical dithieno heteroaromatic compounds include dithieno[3,4-b:3',4'-d]thiophene, 7H-cyclopentano[1,2-c:3,4-c']dithiophene-7-one and 4,4-dimethyl-4H-dithieno[3,4-b:3',4'-d]silole. The synthesis process disclosed by the invention is operable, and the reaction condition is involved with a water-free, oxygen-free and low-temperature condition, thus ensuring that the invention is suitable for laboratory-scale preparation.
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Paragraph 0061-0063
(2017/01/09)
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- Selectivity of Br/Li exchange and deprotonation of 4,4′-dibromo-3, 3′-bithiophene for synthesis of symmetrical and unsymmetrical dithienoheteroaromatic rings
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The novel selective synthesis of symmetrical and unsymmetrical dithienoheteroaromatic rings (DTHAs) has been developed via intramolecular cyclization of 4,4′-dibromo-3,3′-bithiophene (3). Four reaction conditions including n-BuLi/Et2O, n-BuLi/T
- Han, Hui,Zhao, Wenling,Song, Jinsheng,Li, Chunli,Wang, Hua
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p. 2726 - 2730
(2013/04/23)
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- New syntheses of tricyclic thiophenes and cyclic tetrathiophenes using transition-metal-catalyzed cyclization
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New synthetic methods for polycyclic thiophenes were developed. Thus, dithienothiophenes, cyclopentadithiophene, silacyclopentadithiophenes, and cyclooctatetrathiophenes were synthesized in moderate to good yields by using the CuCl2-mediated cyclization of organocopper(I) and organozinc intermediates prepared from dilithio-derivatives with CuCN or ZnCl2, respectively. A direct cyclization of bromothiophene derivatives with hexamethylditin in the presence of tetrakis(triphenylphosphine)palladium(0) also gave dithienothiophenes, cyclopenta-dithiophenes, and silacyclopentadithiophenes in good yields.
- Kabir, S. M. Humayun,Miura, Mami,Sasaki, Shigeru,Harada, Genta,Kuwatani, Yoshiyuki,Yoshida, Masato,Iyoda, Masahiko
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p. 761 - 774
(2007/10/03)
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