naphtho[2,1-b:3,4-b']dithiophene-5,6-diol | 1207251-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: naphtho[2,1-b:3,4-b']dithiophene-5,6-diol
• CAS: 1207251-46-4
• 化学式: C₁₄H₈O₂S₂
• 分子量: 272.348
• InChiKey: GPQMIBTVOBJTOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-甲基溴丁烷 、 naphtho[2,1-b:3,4-b']dithiophene-5,6-diol 在 caesium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以204 mg的产率得到
  参考文献：
  名称：

  2D Assembly of Metallacycles on HOPG by Shape-Persistent Macrocycle Templates

  摘要：

  The synthesis and scanning tunneling microscopy (STM) investigations of shape-persistent arylene-ethynylene-butadiynylene macrocycles along with their codeposites with metallacycles are reported. 2D ordered arrays of macrocycles and macrocycle/metallacycle architectures (1:1) have been obtained on HOPG by self-assembly under ambient conditions. It is found that the ordered macrocycle array acts as a template for the deposition of the adlayer molecules. For each underlying macrocycle, one metallacycle has been detected. The unit-cell data of both, the macrocycles; and their codeposites, show that the structural information of the macrocycle layer is perfectly transformed to the guest molecules. A rather unexpected observation is that the present compound could not be coadsorbed with C-60, indicating that only a minor change in the structure of the macrocycle has a dramatic effect on the ability of the monolayer to bind additional guest molecules.

  DOI：

  10.1021/ja907220f
• 作为产物：
  描述：

  5,6-dimethoxynaphtho[2,1-b:3,4-b']dithiophene 在 三溴化硼 作用下， 以99%的产率得到naphtho[2,1-b:3,4-b']dithiophene-5,6-diol
  参考文献：
  名称：

  5,6-双[9-(2-癸基十四烷基)-9H-咔唑-3-基]萘并[2,1-b:3,4-b']二噻吩作为一种有前途的构建块的合成及光学和电化学性质用于光伏应用

  摘要：

  一种新型含咔唑的萘并二噻吩杂芳族化合物，5,6-双[9-(2-癸基十四烷基)-9H-咔唑-3-基]萘并[2,1-b:3,4-b']二噻吩(M1) ，随后被合成用作弱供体结构，用于根据“弱供体-强受体”概念构建窄带隙 D-A 共轭聚合物。M1的组成和结构由元素分析和IR和1H和13C NMR光谱数据证实。测量了产物的光学和电化学特性。化合物 M1 具有低位 HOMO (–5.57 eV)，有利于高开路电压，适合作为 D-A 共轭聚合物中用于光伏应用的有前途的弱供体部分。

  DOI：

  10.1134/s0012500816030022

文献信息

• 5,6-Bis(9-(2-decyltetradecyl)-6-fluoro-9H-carbazol-3-yl)naphtho[2,1-b:3,4-b']dithiophene as a Promising Donor Structure for D–A Conjugated Copolymers with a Narrow Bandgap
  作者：M. L. Keshtov、S. A. Kuklin、I. O. Konstantinov、A. S. Peregudov、Zhi-Yuan Xie、I. E. Ostapov、E. E. Makhaeva、A. R. Khokhlov

  DOI：10.1134/s0012500818100014

  日期：2018.10

  A new carbazole-containing naphthodithiophene derivativeheteroaromatic compound 5,6- bis[9-(2-decyltetradecyl)-9H-carbazol-3-yl]naphtho[2,1-b:3,4-b']dithiophene (M1)has been synthesized. The compound will be used by us as a weak donor structural block for fabricating narrow-bandgap D-A conjugated polymers. The composition and structure of M1 have been confirmed by elemental analysis data, IR spectroscopy, and H-1 and C-13 NMR. The synthesized compound has a low HOMO energy (-5.4 eV), which is favorable for a high open-circuit voltage. Monomer M1 can be used as a promising weak donor moiety in D-A conjugated polymers for solar photovoltaics.