2,7-Dibromo-4,5-didodecoxythieno[3,2-e][1]benzothiole | 1296207-72-1

• 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: 2,7-Dibromo-4,5-didodecoxythieno[3,2-e][1]benzothiole
• CAS: 1296207-72-1
• 化学式: C₃₄H₅₂Br₂O₂S₂
• 分子量: 716.726
• InChiKey: PIEBHLZVVGAGDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.1
• 重原子数：
  40
• 可旋转键数：
  24
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  硒吩-2-硼酸 、 2,7-Dibromo-4,5-didodecoxythieno[3,2-e][1]benzothiole 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium fluoride 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 26.0h， 以60%的产率得到4,5-Didodecoxy-2,7-di(selenophen-2-yl)thieno[3,2-e][1]benzothiole
  参考文献：
  名称：

  Electrochemical Route to Solution-Processable Polymers of Thiophene/Selenophene Capped Didodecyloxybenzo[1,2-b:4,3-b′]dithiophene and Their Optoelectronic Properties

  摘要：

  Two new solution-processable polymers P1 and P2 are being reported here, which were prepared by electrochemical polymerization of thiophene and selenophene capped 7,8-didodecyloxybenzo[1,2-b:4,3-b']dithiophene (BdT-Dod), respectively and characterized by gel permeation chromatography (GPC) and H-1 NMR. The selenophene containing polymer possesses lower band gap than the thiophene analogue. Density functional theory (DFT) calculation showed the highly curved structure of the polymers and reproduced the trend in their optical band gaps. P2 showed larger bathochromic shift in the absorption spectrum from solution to film state compared to that of P1, which indicates better pi-stacking interaction in the solid state for P2. In spite of having highly curved chains, the polymers successfully exhibited electrochromic switching. The exchange of the end-caps from thiophene to selenophene have manifested with higher electrochromic switching ability and better polaronic and bipolaronic features in spectroelectrochemical measurement of P2 than that of P1. Kinetic study on the polymer films using chronoamperometry revealed that the selenophene containing polymer P2 afforded triangle%T similar to 60 in the visible region with a coloration efficiency of 100 cm(2) C-1. Electrochemical polymerization of BdT-Dod using different solvent/electrolyte systems was unsuccessful.

  DOI：

  10.1021/ma401853q
• 作为产物：
  描述：

  苯并二噻吩-4,5-二酮 在 N-溴代丁二酰亚胺(NBS) 、 caesium carbonate 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 88.0h， 生成 2,7-Dibromo-4,5-didodecoxythieno[3,2-e][1]benzothiole
  参考文献：
  名称：

  苯并[1,2-b:4,3-b']二噻吩-吡啶异构体：合成、自组装、光物理和酸变色特性

  摘要：

  通过 Suzuki 偶联反应作为关键步骤合成了两种苯并[1,2-b:4,3-b']二噻吩-吡啶基弯曲异构体（3BDTPy12和4BDTPy12 ）。它们在吡啶单元上的N原子位置不同，这对其自组装行为和光物理性质产生了显着影响。N在吡啶环对位的4BDTPy12可以自组装成柱状液晶相，而其在吡啶环的间位N的异构体3BDTPy12只是晶体。这两种化合物都可以在不同的有机溶剂中形成凝胶，但具有不同的形态。溶剂极性和掺杂剂的影响，包括手性 L-苯丙氨酸 (L-Phe)，还研究了三氟乙酸和 L-酒石酸对其凝胶形态的影响。L-酒石酸掺杂的4BDTPy12凝胶可产生增强的黄色发射，可用于产生WLED ，该化合物可用作挥发性酸碱蒸气的化学传感器，具有良好的可逆性。

  DOI：

  10.1016/j.dyepig.2022.110490

文献信息

• Empty Helical Nanochannels with Adjustable Order from Low-Symmetry Macrocycles
  作者：Martin Fritzsche、Anne Bohle、Dmytro Dudenko、Ute Baumeister、Daniel Sebastiani、Gabriele Richardt、Hans Wolfgang Spiess、Michael Ryan Hansen、Sigurd Höger

  DOI：10.1002/anie.201007437

  日期：2011.3.21

  Take the tube: Self‐organization of shape‐persistent macrocycles in the liquid‐crystalline phase by π–π stacking leads to empty nanochannels that have an inner diameter above one nanometer and either tight or more permeable walls (see picture). Solid‐state NMR spectroscopy was used to confirm that the channels do not contain solvent molecules or alkyl chains.

  以电子管为例：通过π-π堆积在液晶相中对形状持久性大环的自组织会导致空的纳米通道，其内径大于1纳米，并且壁紧密或具有更多的可渗透性（参​​见图片）。固态NMR光谱用于确认通道不包含溶剂分子或烷基链。
• Benzodithiophene based π-conjugated macrocycles: synthesis, morphology and electrochemical characterization
  作者：Anjan Bedi、Sanjio S. Zade

  DOI：10.1039/c4ob01043d

  日期：——

  A 7,8-didodecyloxybenzo[1,2-b:4,3-b′]dithiophene (BdT-Dod) containing a macrocycle was synthesized from a thiophene capped BdT-Dod comonomer through a Ti(IV) mediated McMurry reaction and characterized by 1H NMR, 13C NMR and MALDI-TOF mass spectrometry. Additionally, the morphological characterization was performed by AFM and SEM to investigate the self-aggregation properties. The macrocycle underwent self-assembly in the solid state to form fibers on the Si/SiO2 surface with a length in the μm range and a thickness of about 400 nm.

  通过Ti(IV)介导的McMurry反应，从噻吩封端的BdT-Dod共聚单体合成了含有大环的7,8-二十二烷氧基苯并[1,2-b:4,3-b²]二噻吩（BdT-Dod），并通过1H NMR、13C NMR和MALDI-TOF质谱法对其进行了表征。此外，还通过AFM和SEM进行了形态学表征，以研究其自聚集特性。大环在固态下进行自组装，在Si/SiO2表面形成纤维，长度在μm范围内，厚度约为400 nm。