2-bromo-5-[2,4,5-tris(5-bromo-2-thienyl)phenyl]thiophene | 871513-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-bromo-5-[2,4,5-tris(5-bromo-2-thienyl)phenyl]thiophene
• 英文别名: 1,2,4,5-tetra(2'-bromo-5'-thienyl)benzene；1,2,4,5-tetrakis(5-bromothiophen-2-yl)benzene
• CAS: 871513-85-8
• 化学式: C₂₂H₁₀Br₄S₄
• 分子量: 722.201
• InChiKey: HMQZLNVGJFPDKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.65
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-bromo-5-[2,4,5-tris(5-bromo-2-thienyl)phenyl]thiophene 在 iron(III) chloride 作用下， 以 硝基甲烷 、 氯苯 为溶剂， 生成 2,5,9,12-tetrabromoanthra[1,2-b:4,3-b':5,6-b'':8,7-b''']tetrathiophene
  参考文献：
  名称：

  室温盘状液晶四硫蒽蒽中的高空穴迁移率。

  摘要：

  探索了一种新的盘状核片段四硫蒽蒽（TTA），当在空间电荷限制电流（SCLC）器件中使用时，在室温下显示出4.22 cm2 V-1 s-1的非常高的空穴迁移率（μh）。TTA核之间的强表面相互作用（π-π，SS）以及导数在SCLC电池中大面积在柱状中间相中垂直排列的趋势很高，这有助于顶级电荷载流子迁移。

  DOI：

  10.1039/d0cc01226b
• 作为产物：
  描述：

  1,2,4,5-tetra(2'-thienyl)benzene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以80%的产率得到2-bromo-5-[2,4,5-tris(5-bromo-2-thienyl)phenyl]thiophene
  参考文献：
  名称：

  室温盘状液晶四硫蒽蒽中的高空穴迁移率。

  摘要：

  探索了一种新的盘状核片段四硫蒽蒽（TTA），当在空间电荷限制电流（SCLC）器件中使用时，在室温下显示出4.22 cm2 V-1 s-1的非常高的空穴迁移率（μh）。TTA核之间的强表面相互作用（π-π，SS）以及导数在SCLC电池中大面积在柱状中间相中垂直排列的趋势很高，这有助于顶级电荷载流子迁移。

  DOI：

  10.1039/d0cc01226b

文献信息

• The synthesis and properties of solution processable phenyl cored thiophene dendrimers
  作者：William J. Mitchell、Nikos Kopidakis、Garry Rumbles、David S. Ginley、Sean E. Shaheen

  DOI：10.1039/b508683c

  日期：——

  In this paper we describe the convergent synthesis of a new class of phenyl cored thiophene dendrimers, which are promising candidates for use in organic semiconductor devices. We have prepared dendrimers with three and four dendrons around the core as well as dendrimers with 1st and 2nd generation dendrons. All the dendrimers were soluble in common organic solvents such as chloroform, THF and toluene. The structures and size properties are confirmed by a number of techniques including NMR, GPC and MALDI-TOF-MS. Decomposition was studied by TGA with initial breakdown of the hexyl surface groups followed by the aromatic core. The spectroscopic properties were studied by UV-vis and PL spectrometry which demonstrated substantial differences between the dendrimers with three and four dendrons. Optical band gaps varied between 2.34 and 2.60 eV for thin films of the dendrimers and electronic band gaps were, on average, 0.3 eV greater than the optical band gaps. The smallest band gap was measured for the dendrimer with four 2nd generation dendrons around the phenyl core. Fluorescence lifetimes of the molecules in solution ranged from 200 to 560 ps. This range in values was attributed to differences in internal conversion rates associated with varying degrees of flexibility of the extended dendrons.

  在本文中，我们介绍了一种新型苯基芯噻吩树枝形分子的聚合合成方法，这种树枝形分子有望用于有机半导体器件。我们制备了核心周围有三个和四个树枝状分子的树枝状聚合物，以及有第一代和第二代树枝状分子的树枝状聚合物。所有树枝状聚合物均可溶于氯仿、四氢呋喃和甲苯等常见有机溶剂。核磁共振、气相色谱和 MALDI-TOF-MS 等多种技术证实了它们的结构和尺寸特性。通过热重分析法研究了分解情况，首先分解的是己基表面基团，然后是芳香族核心。通过紫外-可见光光谱法和聚光光谱法对光谱特性进行了研究，结果表明具有三个和四个树枝的树枝状聚合物之间存在很大差异。树枝状聚合物薄膜的光学带隙介于 2.34 和 2.60 eV 之间，电子带隙平均比光学带隙大 0.3 eV。苯核周围有四个第二代树枝状分子的树枝状聚合物的带隙最小。溶液中分子的荧光寿命从 200 到 560 ps 不等。之所以会出现这样的数值范围，是因为扩展树枝的柔韧性不同，内部转换率也不同。
• Star-shaped and linear π-conjugated oligomers consisting of a tetrathienoanthracene core and multiple diketopyrrolopyrrole arms for organic solar cells
  作者：Hideaki Komiyama、Chihaya Adachi、Takuma Yasuda

  DOI：10.3762/bjoc.12.142

  日期：——

  Solution-processable star-shaped and linear π-conjugated oligomers consisting of an electron-donating tetrathienoanthracene (TTA) core and electron-accepting diketopyrrolopyrrole (DPP) arms, namely, TTA-DPP4 and TTA-DPP2, were designed and synthesized. Based on density functional theory calculations, the star-shaped TTA-DPP4 has a larger oscillator strength than the linear TTA-DPP2, and consequently, better photoabsorption property over a wide range of visible wavelengths. The photovoltaic properties of organic solar cells based on TTA-DPP4 and TTA-DPP2 with a fullerene derivative were evaluated by varying the thickness of the bulk heterojunction active layer. As a result of the enhanced visible absorption properties of the star-shaped π-conjugated structure, better photovoltaic performances were obtained with relatively thin active layers (40–60 nm).

  可溶性的星形和线性π-共轭寡聚物，由一个电子给体四硫基蒽核心和一个电子受体二酮吡咯烷基(DPP)臂组成，分别命名为TTA-DPP4和TTA-DPP2。基于密度泛函理论计算，星形TTA-DPP4具有比线性TTA-DPP2更大的振荡强度，因此在可见光波长范围内具有更好的光吸收性能。通过改变体异质结活性层的厚度，评估了基于TTA-DPP4和TTA-DPP2与富勒烯衍生物的有机太阳能电池的光伏性能。由于星形π-共轭结构具有增强的可见光吸收性能，因此在相对较薄的活性层（40-60 nm）中获得了更好的光伏性能。
• Functionalized Tetrathienoanthracene: Enhancing π–π Interactions Through Expansion of the π-Conjugated Framework
  作者：Alicea A. Leitch、Aya Mansour、Kimberly A. Stobo、Ilia Korobkov、Jaclyn L. Brusso

  DOI：10.1021/cg201521w

  日期：2012.3.7

  The functionalization of tetrathienoanthracene (TTA) with bromine and 2-hexylthiophene moieties is described, and their influence at both the molecular and solid-state level has been investigated. Comparative optical and electrochemical studies indicate an increase in conjugation for the thiophene derivative compared to the parent TTA. In the solid state, these materials form slipped pi-stack structures with a number of close intermolecular contacts. Comparison of the two structures reveals a more steeply inclined slipped pi-stack for the thiophene derivative resulting in a closer interplanar separation. This, coupled with the extended molecular framework, leads to an enhanced number of pi-pi interactions within the stack. The combination of increased conjugation at the molecular level, and pi-stacked structures with strong intermolecular communication at the solid-state level, augurs well for the use of TTA materials in optoelectronic applications.