2,5-dibromo-3,6-bis(2-ethylhexylsulfonyl)thieno[3,2-b]-thiophene | 1492981-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: 2,5-dibromo-3,6-bis(2-ethylhexylsulfonyl)thieno[3,2-b]-thiophene
• 英文别名: 2,5-Dibromo-3,6-bis(2-ethylhexylsulfonyl)thieno[3,2-b]thiophene；2,5-dibromo-3,6-bis(2-ethylhexylsulfonyl)thieno[3,2-b]thiophene
• CAS: 1492981-46-0
• 化学式: C₂₂H₃₄Br₂O₄S₄
• 分子量: 650.582
• InChiKey: SLGLAGBCCGLISC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-乙基己基二硫醚 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 45.0h， 生成 2,5-dibromo-3,6-bis(2-ethylhexylsulfonyl)thieno[3,2-b]-thiophene
  参考文献：
  名称：

  Tuning the Electronic Properties of Poly(thienothiophene vinylene)s via Alkylsulfanyl and Alkylsulfonyl Substituents

  摘要：

  The use of alkylsulfanyl and alkylsulfonyl side chains are demonstrated to be a useful synthetic strategy for tuning the electronic properties of organic semiconductors, as shown in thienothiophene vinylene polymers. By changing the oxidation state of sulfanyl to sulfonyl, we lower the HOMO and LUMO energy levels of our substituted polymers, as well as enhance their fluorescence. Fine-tuning of the energy levels was achieved by combining sulfanyl and sulfonyl substituted thienothiophene monomers through random polymerization, yielding polymers with low-band gaps (1.5 eV) yet benefiting from a structurally uniform conjugated backbone. The effects of these functional side chains are presented through DFT calculations, UV-vis, fluorescence, and electrochemical measurements, as well as crystallographic analysis of a sulfanyl-substituted oligomer. The semiconducting properties of the new polymers are studied in OFET and OPV devices.

  DOI：

  10.1021/ma402018n

文献信息

• Tuning the Electronic Properties of Poly(thienothiophene vinylene)s via Alkylsulfanyl and Alkylsulfonyl Substituents
  作者：Julia A. Schneider、Afshin Dadvand、Wen Wen、Dmitrii F. Perepichka

  DOI：10.1021/ma402018n

  日期：2013.12.10

  The use of alkylsulfanyl and alkylsulfonyl side chains are demonstrated to be a useful synthetic strategy for tuning the electronic properties of organic semiconductors, as shown in thienothiophene vinylene polymers. By changing the oxidation state of sulfanyl to sulfonyl, we lower the HOMO and LUMO energy levels of our substituted polymers, as well as enhance their fluorescence. Fine-tuning of the energy levels was achieved by combining sulfanyl and sulfonyl substituted thienothiophene monomers through random polymerization, yielding polymers with low-band gaps (1.5 eV) yet benefiting from a structurally uniform conjugated backbone. The effects of these functional side chains are presented through DFT calculations, UV-vis, fluorescence, and electrochemical measurements, as well as crystallographic analysis of a sulfanyl-substituted oligomer. The semiconducting properties of the new polymers are studied in OFET and OPV devices.