seleno[3,4-b]thiophene | 74070-00-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硒吩
• 英文名称: seleno[3,4-b]thiophene
• 英文别名: selenolo[3,4-b]thiophene；S34bT；Selenolo(3,4-b)thiophene；selenopheno[3,4-b]thiophene
• CAS: 74070-00-1
• 化学式: C₆H₄SSe
• 分子量: 187.124
• InChiKey: FDQBVFRTDAGNHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  seleno[3,4-b]thiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以90%的产率得到4,6-dibromoselenolo[2,3-c]thiophene
  参考文献：
  名称：

  Tuning the Band Gap of Low-Band-Gap Polyselenophenes and Polythiophenes: The Effect of the Heteroatom

  摘要：

  A series of new low-band-gap thieno- or selenolo-fused polyselenophenes (P5 and P6) and selenolo-fused polythiophene (P4) (as well as previously reported thieno-fused polythiophene, P3) was prepared systematically by electropolymerization (P4-P6) and by solid-state polymerization (P3, P5 and P6). The 2,5-dibrominated monomers (3Br(2), 5Br(2), and 6Br(2)) undergo solid-state polymerization under slight heating and produce insoluble P3, P5, and P6 as black conducting powders. The spectroelectrochemically measured optical band gaps of P4-P6 films are 0.96, 0.72, and 0.76 eV, respectively. DFT calculations performed on P3-P6 provide excellent estimations of the experimental band gaps of these polymers. The band gap of the polyselenophenes (P5 and P6) is 0.2 eV lower than that of the corresponding polythiophenes (P3 and P4). We introduced a new scheme for band gap control in conjugated polymers by replacing the sulfur atom with a selenium atom in the main and/or peripheral ring, which leads to significant and predictable changes in the band gap of the polymers. This is due to the lower aromaticity of a selenophene ring compared to a thiophene ring. Thus, we have achieved band gap control in very low band gap (similar to 0.7-1.0 eV) polymers through the use of different combinations of selenium and sulfur atoms in the main and peripheral rings.

  DOI：

  10.1021/cm102395v
• 作为产物：
  描述：

  3-bromo-4-(trimethylsilyl)ethynylselenophene 在 正丁基锂 、 水 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 4.5h， 生成 seleno[3,4-b]thiophene
  参考文献：
  名称：

  Tuning the Band Gap of Low-Band-Gap Polyselenophenes and Polythiophenes: The Effect of the Heteroatom

  摘要：

  A series of new low-band-gap thieno- or selenolo-fused polyselenophenes (P5 and P6) and selenolo-fused polythiophene (P4) (as well as previously reported thieno-fused polythiophene, P3) was prepared systematically by electropolymerization (P4-P6) and by solid-state polymerization (P3, P5 and P6). The 2,5-dibrominated monomers (3Br(2), 5Br(2), and 6Br(2)) undergo solid-state polymerization under slight heating and produce insoluble P3, P5, and P6 as black conducting powders. The spectroelectrochemically measured optical band gaps of P4-P6 films are 0.96, 0.72, and 0.76 eV, respectively. DFT calculations performed on P3-P6 provide excellent estimations of the experimental band gaps of these polymers. The band gap of the polyselenophenes (P5 and P6) is 0.2 eV lower than that of the corresponding polythiophenes (P3 and P4). We introduced a new scheme for band gap control in conjugated polymers by replacing the sulfur atom with a selenium atom in the main and/or peripheral ring, which leads to significant and predictable changes in the band gap of the polymers. This is due to the lower aromaticity of a selenophene ring compared to a thiophene ring. Thus, we have achieved band gap control in very low band gap (similar to 0.7-1.0 eV) polymers through the use of different combinations of selenium and sulfur atoms in the main and peripheral rings.

  DOI：

  10.1021/cm102395v

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。
• Heterocyclic Fused Selenophene Monomers
  申请人：Zahn Steffen

  公开号：US20090018348A1

  公开（公告）日：2009-01-15

  A heterocyclic fused selenophenes and a method of making a heterocyclic fused selenophenes of formula (1): wherein X is S or Se, Y is S or Se, wherein one or both of X and Y is Se, R is a substituent group. The monomer being capable of polymerization to form an electrically conductive polymer or oligomer.

  一种杂环融合硒吲哚及制备该杂环融合硒吲哚的方法，其化学式如下（1）：其中X为S或Se，Y为S或Se，其中X和/或Y中的一个或两个为Se，R为取代基。该单体能够聚合形成电导聚合物或寡聚物。
• KONAR, A.;LITVINOV, V., CHEM. SCR., 1982, 19, N 4, 176-181
  作者：KONAR, A.、LITVINOV, V.

  DOI：——

  日期：——