2-bromo-3-(octylsulfanyl)thiophene | 917395-42-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-bromo-3-(octylsulfanyl)thiophene
• 英文别名: 2-Bromo-3-octylsulfanylthiophene
• CAS: 917395-42-7
• 化学式: C₁₂H₁₉BrS₂
• 分子量: 307.319
• InChiKey: SUGYWRIAAJIOBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-3-(octylsulfanyl)thiophene 在 四(三苯基膦)钯 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 73.0h， 生成 4-(octylsulfanyl)-5,5'-bis(trimethylsilyl)-2,2'-bithiophene
  参考文献：
  名称：

  One-Pot Synthesis of Symmetric Octithiophenes from Asymmetric β-Alkylsulfanyl Bithiophenes

  摘要：

  Starting from 4-(octylsulfanyl)-2,2'-bithiophene, 4-bromo-4'-(octylsulfanyl)-2,2'-bithiophene, 4-iodo-4'-(octylsulfanyl)-2,2'-bithiophene, 4-bromo-4'-[(S)-2-methylbutylsulfanyl]-2,2'-bithiophene, and 4-iodo-4'-[(S)-2-methylbutylsulfanyl]-2,2'-bithiophene, a new series of symmetrically beta-substituted octithiophenes were synthesized by one-pot oxidative coupling with FeCl3. The octithiophenes obtained are soluble in common organic solvents and show different solvatochromic properties depending on the substitution type. In particular, the bromine atom exerts a positive influence on the supramolecular organization: the brominated octithiophenes display high filmability, solvatochromism, and CD induced by aggregation (when the chiral 2-methylbutylsulfanyl group is present), properties usually observed for polythiophenes. Density functional theory (DFT) calculations were carried out an a model bithiophene (4-substituted with a methylsulfanyl group) in order to understand the possible mechanism of the growth, the regiochemistry, and the reason for the polymerization leads to an octithiophene.

  DOI：

  10.1021/ma0614141
• 作为产物：
  描述：

  3-(octylsulfanyl)thiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以97%的产率得到2-bromo-3-(octylsulfanyl)thiophene
  参考文献：
  名称：

  One-Pot Synthesis of Symmetric Octithiophenes from Asymmetric β-Alkylsulfanyl Bithiophenes

  摘要：

  Starting from 4-(octylsulfanyl)-2,2'-bithiophene, 4-bromo-4'-(octylsulfanyl)-2,2'-bithiophene, 4-iodo-4'-(octylsulfanyl)-2,2'-bithiophene, 4-bromo-4'-[(S)-2-methylbutylsulfanyl]-2,2'-bithiophene, and 4-iodo-4'-[(S)-2-methylbutylsulfanyl]-2,2'-bithiophene, a new series of symmetrically beta-substituted octithiophenes were synthesized by one-pot oxidative coupling with FeCl3. The octithiophenes obtained are soluble in common organic solvents and show different solvatochromic properties depending on the substitution type. In particular, the bromine atom exerts a positive influence on the supramolecular organization: the brominated octithiophenes display high filmability, solvatochromism, and CD induced by aggregation (when the chiral 2-methylbutylsulfanyl group is present), properties usually observed for polythiophenes. Density functional theory (DFT) calculations were carried out an a model bithiophene (4-substituted with a methylsulfanyl group) in order to understand the possible mechanism of the growth, the regiochemistry, and the reason for the polymerization leads to an octithiophene.

  DOI：

  10.1021/ma0614141

文献信息

• Optoelectronic Properties of A‐π‐D‐π‐A Thiophene‐Based Materials with a Dithienosilole Core: An Experimental and Theoretical Study
  作者：Monica Caselli、Davide Vanossi、Mirko Buffagni、Manuel Imperato、Laura Pigani、Adele Mucci、Francesca Parenti

  DOI：10.1002/cplu.201900092

  日期：2019.9

  Two A-π-D-π-A thiophene-based small molecules with a central dithienosilole core and dicyanovinyl (DCV) end groups were synthesized. These compounds differ only by the presence of alkyl and alkylsulfanyl chains, respectively, on the thiophene beta positions. Computational data together with the spectroscopic and electrochemical findings (obtained by means of absorption, steady-state/time-resolved emission

  合成了两个具有中央二噻吩甲硅油烯核心和双氰基乙烯基（DCV）端基的A-π-D-π-A噻吩基小分子。这些化合物的区别仅在于噻吩β位置分别存在烷基和烷基硫烷基链。计算数据以及光谱和电化学结果（通过吸收，稳态/时间分辨发射技术和循环伏安法获得）表明，这两种分子均具有低的电子和光学带隙，宽的吸收光谱以及良好的稳定性处于p和n掺杂状态，使其适合于光电应用。在这两种化合物中，HOMO-LUMO跃迁都涉及分子内电荷从电子给体二硫杂硅醇单元转移到两个末端电子受体DCV基团的过程。对于两个分子均观察到明显的正发射溶剂变色现象，并基于在S1激发态下的对称性断裂来解释。还将这两种合成的化合物与其较短的前体和类似的寡噻吩进行了比较，以了解构件的性质如何影响最终材料的特性。此外，有可能更好地理解硫原子在调节所研究的小分子的光学性质中的作用。还将这两种合成的化合物与其较短的前体和类似的寡噻吩进行了比较，以了解构件的性
• (Alkylsulfanyl)bithiophene-alt-Fluorene: π-Conjugated Polymers for Organic Solar Cells
  作者：Francesca Parenti、Pasquale Morvillo、Eugenia Bobeico、Rosita Diana、Massimiliano Lanzi、Claudio Fontanesi、Francesco Tassinari、Luisa Schenetti、Adele Mucci

  DOI：10.1002/ejoc.201100738

  日期：2011.10

  bithienyl unit and different alkylsulfanyl chain lengths. The structural, electrochemical and photophysical properties of these polymers were investigated by gel permeation chromatography (GPC), differential scanning calorimetry (DSC), NMR, UV/Vis and photoluminescence (PL) spectroscopy and cyclic voltammetry (CV), and the polymers were used to assemble organic solar cells (OSCs), in combination with

  我们描述了具有不同联噻吩基单元区域化学和不同烷基硫烷基链长的交替联噻吩 - 芴共聚物（P1-P3）的合成。通过凝胶渗透色谱 (GPC)、差示扫描量热法 (DSC)、核磁共振、紫外/可见光和光致发光 (PL) 光谱和循环伏安法 (CV) 研究了这些聚合物的结构、电化学和光物理性质，并使用了聚合物组装有机太阳能电池 (OSC)，结合富勒烯衍生物甲基 [6,6]-苯基-C61-丁酸酯 (PCBM)。具有头对头二噻吩基单元的 P3 相对于具有尾对尾二噻吩基单元的 P1 和 P2 显示出更宽的吸收和更低的带隙。P1-P3 的 PL 强度在 PCBM 存在下急剧淬灭，证明供体和受体之间发生了有效的电荷转移。最好的 OSC 设备是用 P3 获得的。