3339-80-8Relevant articles and documents
Synthesis of β-Methoxy, Methyl-Capped α-Oligothiophenes
Miller, Larry L.,Yu, Yuan
, p. 6813 - 6819 (1995)
The first syntheses of structurally defined methoxyoligothiophenes are described.Nine α-coupled oligothiophenes, dimers through hexamers, symmetrically substituted at the "inside" or "outside" β-positions with two or four methoxy groups, and with terminal methyl groups, were prepared.The electron-donor methoxy groups and terminal methyls have been shown to stabilize cationic species formed by oxidation or protonation of these oligomers.The oligomers were built up by the cross coupling of (mono- or oligo-) β-methoxy-α-iodothiophenes and (mono- or oligo-) α-stannylthiophenes catalyzed by Pd(0)/Pd(II) or by the redox homo-coupling of α-thienyllithium compounds with Fe(acac)3.Synthesis by the cross coupling of thienyl Grignard reagents and bromothiophenes with Ni(0) or Suzuki coupling using organoboranes was not successful.An X-ray crystal structure od a dimethoxy quaterthiophene is reported.
Conjugated Oligothiophene Derivatives Based on Bithiophene with Unsaturated Bonds as Building Blocks for Solution-Processed Bulk Heterojunction Organic Solar Cells
Cui, Chaohua,Wu, Yue,Cheung, Man-Sing,Ho, Cheuk-Lam,Dong, Qingchen,Lin, Zhenyang,Li, Yongfang,Wong, Wai-Yeung
, p. 3557 - 3567 (2016/12/26)
A new building block ATVTA that uses stiff carbon–carbon triple bonds (A) on 1,2-di(2-thienyl)-ethene (TVT) has been developed. Oligothiophene derivatives S-01 with a TVT unit, S-02 with a 5,5′-diethynyl-2,2′-dithienyl (AT2) unit and S-03 with ATVTA were synthesized to compare their effects in a systematic study. Due to the better π-conjugation extension of the TVT unit, S-01 exhibits the most red-shifted absorption profile among them, whereas S-02 possesses the deepest HOMO level. While the HOMO level of S-03 is down-shifted by 0.02 eV relative to that of S-01, the alkyne linkages can effectively down-shift the HOMO level. By replacing the terminal units of S-03 with stronger electron acceptors, S-04 and S-05 exhibited broader absorption profiles and lower HOMO levels than those of S-03. Organic solar cells based on these molecules were fabricated and an S-03:PC60BM (1:1, w/w) based device afforded the highest Voc value of 0.96 V and a power conversion efficiency (PCE) of 2.19 %.
One-pot, regioselective consecutive multihalogenation of 2,2′-bithiophene
Kim, Bo Ram,Kim, Eun Jung,Sung, Gi Hyeon,Kim, Jeum-Jong,Shin, Dong-Soo,Lee, Sang-Gyeong,Yoon, Yong-Jin
supporting information, p. 2788 - 2791 (2013/06/27)
The one-pot regioselective consecutive multihalogenation of 2,2′-bithiophene (1) was demonstrated. Compound 1 was consecutively halogenated with lithium halides such as lithium bromide, chloride, and/or iodide in the presence of lead tetraacetate in chloroform at room temperature or under reflux conditions to give 5-bromo(or chloro)-5′-iodo(or chloro)-, 3-bromo(or chloro)-5,5′-dibromo(or dichloro, diiodo)-, 3,3′-dibromo-(or dichloro)-5,5′-diiodo(or dibromo, dichloro)-, and 3,3′,5-tribromo(or trichloro)-5′-iodo(or bromo)-2,2′- bithiophenes. Notably, this process offers a regioselective method for consecutive multihalogenation in one pot, and the yields and selectivity are also higher than those obtained in the step-by-step and concurrent halogenation methods. Copyright
