2-octylthieno[3,4-b]thiophene | 1221182-02-0

• 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-octylthieno[3,4-b]thiophene
• 英文别名: 2-Octylthieno[3,4-b]thiophene；2-octylthieno[2,3-c]thiophene
• CAS: 1221182-02-0
• 化学式: C₁₄H₂₀S₂
• 分子量: 252.445
• InChiKey: FDEVBASEWHSXPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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-octylthieno[3,4-b]thiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以88%的产率得到4,6-dibromo-2-octylthieno[3,4-b]thiophene
  参考文献：
  名称：

  具有不同烷基侧链长度的可溶低带隙噻吩噻吩聚合物的合成及光物理性质

  摘要：

  我们报告了各种长度的烷基侧链的一类噻吩噻吩聚合物的简便合成和表征。通过两步操作合成了一系列2-烷基噻吩并[3,4- b ]噻吩单体（Ttx），总产率为28-37％。聚（2-烷基噻吩并[3,4- b ]噻吩）（PTtx，烷基：戊基，己基，庚基，辛基和十三烷基）是通过FeCl 3氧化聚合或格氏（Grignard）复分解（GRIM）聚合方法合成的。该聚合物容易溶于普通的有机溶剂。通过GRIM聚合方法（PTtx‐G）合成的聚合物具有较窄的分子量分布（Đ）和较低的分子量（M n），而不是通过氧化聚合（PTtx-O）合成的那些。通过紫外可见光谱，循环伏安法和紫外光电子能谱研究了具有不同长度烷基侧链的聚合物的能带结构。这些低带隙聚合物是有机晶体管，有机发光二极管和有机光伏电池的理想候选材料。©2011 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2011年

  DOI：

  10.1002/pola.24761
• 作为产物：
  描述：

  3-bromo-4-(dec-1-yn-1-yl)thiophene 在 sodium sulfide 、 copper(II) oxide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 以44%的产率得到2-octylthieno[3,4-b]thiophene
  参考文献：
  名称：

  Thieno[3,4-b]thiophene Acceptors with Alkyl, Aryl, Perfluoroalkyl, and Perfluorophenyl Pendants for Donor–Acceptor Low Bandgap Polymers

  摘要：

  We report the design, synthesis, and characterization of a series of thieno[3,4-b]thiophene acceptor blocks with octyl (T8), phenyl (TP), perfluorooctyl (TF8), and perfluorophenyl (TFP) side groups. Their subsequent copolymerization with dithienylbenzodithiophene by direct arylation polymerization afforded novel low bandgap poly(thienothiophene-alt-dithienylbenzodithiophene) (PTB) polymers. The strongly electron with-drawing TF8 and TFP groups were shown to significantly lower both E-HOMO and E-LUMO levels and gave computed copolymer ground-to-excited state dipole changes (triangle mu(ge)) that were relatively higher than for the nonfluorinated analogues. These materials show favorably aligned energy levels relative to conventional fullerene-type acceptors, which should allow them to perform well in organic photovoltaics.

  DOI：

  10.1021/ma4019476

文献信息

• 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。
• Thieno[3,4-<i>b</i>]thiophene Acceptors with Alkyl, Aryl, Perfluoroalkyl, and Perfluorophenyl Pendants for Donor–Acceptor Low Bandgap Polymers
  作者：Patrick D. Homyak、Jonathan Tinkham、Paul M. Lahti、E. Bryan Coughlin

  DOI：10.1021/ma4019476

  日期：2013.11.26

  We report the design, synthesis, and characterization of a series of thieno[3,4-b]thiophene acceptor blocks with octyl (T8), phenyl (TP), perfluorooctyl (TF8), and perfluorophenyl (TFP) side groups. Their subsequent copolymerization with dithienylbenzodithiophene by direct arylation polymerization afforded novel low bandgap poly(thienothiophene-alt-dithienylbenzodithiophene) (PTB) polymers. The strongly electron with-drawing TF8 and TFP groups were shown to significantly lower both E-HOMO and E-LUMO levels and gave computed copolymer ground-to-excited state dipole changes (triangle mu(ge)) that were relatively higher than for the nonfluorinated analogues. These materials show favorably aligned energy levels relative to conventional fullerene-type acceptors, which should allow them to perform well in organic photovoltaics.
• Synthesis and photophysical properties of soluble low-bandgap thienothiophene polymers with various alkyl side-chain lengths
  作者：Woo Jin Bae、Christopher Scilla、Volodimyr V. Duzhko、Won Ho Jo、E. Bryan Coughlin

  DOI：10.1002/pola.24761

  日期：2011.8.1

  Grignard metathesis (GRIM) polymerization methods. The polymers are readily soluble in common organic solvents. The polymers synthesized by GRIM polymerization method (PTtx‐G) have narrower molecular weight distribution (Đ) with lower molecular weight (Mn) than those synthesized by oxidative polymerization (PTtx‐O). The band structures of the polymers with various lengths of alkyl side chains were investigated

  我们报告了各种长度的烷基侧链的一类噻吩噻吩聚合物的简便合成和表征。通过两步操作合成了一系列2-烷基噻吩并[3,4- b ]噻吩单体（Ttx），总产率为28-37％。聚（2-烷基噻吩并[3,4- b ]噻吩）（PTtx，烷基：戊基，己基，庚基，辛基和十三烷基）是通过FeCl 3氧化聚合或格氏（Grignard）复分解（GRIM）聚合方法合成的。该聚合物容易溶于普通的有机溶剂。通过GRIM聚合方法（PTtx‐G）合成的聚合物具有较窄的分子量分布（Đ）和较低的分子量（M n），而不是通过氧化聚合（PTtx-O）合成的那些。通过紫外可见光谱，循环伏安法和紫外光电子能谱研究了具有不同长度烷基侧链的聚合物的能带结构。这些低带隙聚合物是有机晶体管，有机发光二极管和有机光伏电池的理想候选材料。©2011 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2011年