2-dodecylthieno[3,4-b]thiophene | 1202695-60-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-dodecylthieno[3,4-b]thiophene
• 英文别名: 2-Dodecylthieno[2,3-c]thiophene
• CAS: 1202695-60-0
• 化学式: C₁₈H₂₈S₂
• 分子量: 308.552
• InChiKey: SJPREUUKQXCLSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-dodecylthieno[3,4-b]thiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以80%的产率得到2-hexyl-4,6-bis(trimethylstannyl)thieno[3,4-b]-thiophene
  参考文献：
  名称：

  Synthesis of thieno[3,4-b]thiophene, thieno[3,4-b]furan, related compounds and their derivatives and use thereof

  摘要：

  本文揭示了制备融合杂环化合物（如噻吩并[3,4-b]噻吩、噻吩并[3,4-b]呋喃等）及其衍生物的廉价和简便方法。同时还揭示了由这些融合杂环化合物制备的规则构型聚合物。

  公开号：

  US08168671B2
• 作为产物：
  描述：

  1-碘十二烷 在 lithium aluminium tetrahydride 、 正丁基锂 、 sodiumsulfide nonahydrate 、 三溴化磷 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.75h， 生成 2-dodecylthieno[3,4-b]thiophene
  参考文献：
  名称：

  Synthesis of thieno[3,4-b]thiophene, thieno[3,4-b]furan, related compounds and their derivatives and use thereof

  摘要：

  本文揭示了制备融合杂环化合物（如噻吩并[3,4-b]噻吩、噻吩并[3,4-b]呋喃等）及其衍生物的廉价和简便方法。同时还揭示了由这些融合杂环化合物制备的规则构型聚合物。

  公开号：

  US08168671B2

文献信息

• SYNTHESIS OF THIENO[3,4-b]THIOPHENE, THIENO[3,4-b]FURAN, RELATED COMPOUNDS AND THEIR DERIVATIVES AND USE THEREOF
  申请人：Sotzing Gregory A.

  公开号：US20090326187A1

  公开（公告）日：2009-12-31

  Inexpensive and facile methods of preparing fused heterocycles such as thieno[3,4-b]thiophene, thieno[3,4-b]furan, related compounds, and their derivatives are disclosed. Also disclosed are regioregular polymers prepared from the fused heterocycles.

  揭示了制备噻吩并[3,4-b]噻吩、噻吩并[3,4-b]呋喃、相关化合物及其衍生物的廉价且简便的方法。还揭示了由这些融合杂环制备的规则寡聚物。
• Versatile synthesis of 3,4-b diheteropentalenes
  作者：Tanmoy Dey、Daminda Navarathne、Michael A. Invernale、Ian D. Berghorn、Gregory A. Sotzing

  DOI：10.1016/j.tetlet.2010.02.036

  日期：2010.4

  We describe a new route for the synthesis of thieno[3,4-b]thiophene, alkyl derivatives thereof, seleno[3,4-b]thiophene, and thieno[3,4-b]furan made from inexpensive starting materials, such as thiophene-2-carboxylic acid and furan-2-carboxylic acid. Such fused heterocycles are of great interest for low band gap organic semiconductors and applications including OLEDs, organic photovoltaic cells, and

  我们描述了一种由廉价的起始原料制备的合成噻吩并[3,4- b ]噻吩，其烷基衍生物，硒代[3,4- b ]噻吩和噻吩并[3,4- b ]呋喃的新途径。作为噻吩-2-羧酸和呋喃-2-羧酸。这样的稠合杂环对于低带隙有机半导体以及包括OLED，有机光伏电池和电致变色的应用非常感兴趣。
• Syntheses and Photovoltaic Properties of Narrow Band Gap Donor–Acceptor Copolymers with Carboxylate-Substituted Benzodithiophene as Electron Acceptor Unit
  作者：Kosuke Shibasaki、Kenichi Tabata、Yohei Yamamoto、Takeshi Yasuda、Masashi Kijima

  DOI：10.1021/ma501078e

  日期：2014.8.12

  Stile-coupling of carboxylate-substituted dibrominated benzodithiophene (BDTC) with 2,5-distannylthieno-[3,4-b]thiophene gave novel donor acceptor type alternating copolymers, PBDTC-TT, where BDTC works as an electron-accepting unit in the polymers. They showed broad absorption bands from 500 nm to the near-infrared region, optical band gap (E-g) about 1.5 eV, small pi-stacking distance (3.6 angstrom), and good thermal stability. The hole mobilities of PBDTC-TT determined from performance of their organic field-effect transistors were 3.1-6.9 x 10(-4) (cm(2) V-1 s(-1)). The bulk heterojunction (BHJ) solar cells were fabricated with configuration of ITO/PEDOT:PSS/polymer:PC70BM/LiF/Al. A PBDTC-TT device exhibited photocurrent response upon exposure to light with wavelength of 300-900 nm and incident photon to current conversion efficiency over 40% in the range of 400-750 nm. The power conversion efficiency of the best-performed device reached 3.03% with short-circuit current density of 12.54 mA cm(-2), fill factor of 0.48, and open circuit voltage of 0.51 V under illumination of AM 1.5 G/100 mW cm(-2). These results show that the BDTC unit can behave as an electron accepting building block for donor acceptor type narrow band gap polymers, and these types of polymers can be used as a donor material in the active layer for BHJ photovoltaic cells.
• US8168671B2
  申请人：——

  公开号：US8168671B2

  公开（公告）日：2012-05-01