2,5,9,12-tetrabromoanthra[1,2-b:4,3-b':5,6-b'':8,7-b''']tetrathiophene | 1018950-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,5,9,12-tetrabromoanthra[1,2-b:4,3-b':5,6-b'':8,7-b''']tetrathiophene
• 英文别名: 2,5,9,12-tetrabromoanthra[1,2-b:4,3-b’:5,6-b”:8,7-b”’]tetratiophene；2,5,9,12-tetrabromotrithieno[2',3':5,6:3',2':3,4:3',2':7,8]anthra[1,2-b]thiophene；6,11,19,24-Tetrabromo-5,12,18,25-tetrathiaheptacyclo[14.10.0.03,14.04,8.09,13.017,21.022,26]hexacosa-1(16),2,4(8),6,9(13),10,14,17(21),19,22(26),23-undecaene；6,11,19,24-tetrabromo-5,12,18,25-tetrathiaheptacyclo[14.10.0.03,14.04,8.09,13.017,21.022,26]hexacosa-1(16),2,4(8),6,9(13),10,14,17(21),19,22(26),23-undecaene
• CAS: 1018950-14-5
• 化学式: C₂₂H₆Br₄S₄
• 分子量: 718.17
• InChiKey: ZRVKYWLJOJTSHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,3-tris(decyloxy)-5-ethynylbenzene 、 2,5,9,12-tetrabromoanthra[1,2-b:4,3-b':5,6-b'':8,7-b''']tetrathiophene 在 三乙胺 、 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.25h， 生成
  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：

  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

文献信息

• Oligothiophene-Functionalized Benzene and Tetrathienoanthracene: Effect of Enhanced π-Conjugation on Optoelectronic Properties, Self-Assembly and Device Performance
  作者：Alicea A. Leitch、Kimberly A. Stobo、Bashir Hussain、Mireille Ghoussoub、Saeedeh Ebrahimi-Takalloo、Peyman Servati、Ilia Korobkov、Jaclyn L. Brusso

  DOI：10.1002/ejoc.201300731

  日期：2013.9

  The versatility of fourfold Stille coupling to afford oligothiophene-functionalized tetrathienoanthracene (TTA) and benzene derivatives is described. The influence of the larger, more rigid TTA core on the electronic and structural properties was investigated. Comparative optical and electrochemical studies demonstrate a diminishing HOMO–LUMO gap as the length of the oligothiophene chain increases

  描述了四重 Stille 耦合的多功能性，以提供低聚噻吩官能化的四噻吩蒽 (TTA) 和苯衍生物。研究了更大、更刚性的 TTA 核对电子和结构特性的影响。比较光学和电化学研究表明，随着低聚噻吩链的长度增加，HOMO-LUMO 间隙减小，刚性 TTA 化合物比更灵活的苯类似物表现出更低的能隙。X 射线晶体学研究表明，噻吩取代的 TTA 结构由滑动的 π 堆栈和几个紧密的堆栈内 π-π 相互作用组成；由于噻吩配体在平面外扭曲，没有观察到苯衍生物的紧密接触。最后，苯类似物中的分子与它们的邻居分离。噻吩和联噻吩官能化的 TTA 化合物被制造成底部接触配置的 OTFT 器件，并表现出大约 10 的迁移率。10–4 cm2 V–1 s–1 和超过四个数量级的开/关比。
• 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.
• High hole mobility in room temperature discotic liquid crystalline tetrathienoanthracenes
  作者：Indu Bala、Joydip De、Santosh Prasad Gupta、Harpreet Singh、Upendra Kumar Pandey、Santanu Kumar Pal

  DOI：10.1039/d0cc01226b

  日期：——

  Tetrathienoanthracene (TTA), a new discotic core fragment, is explored that shows a remarkably high hole mobility (μh) of 4.22 cm2 V-1 s-1 at room temperature when used in space-charge limited current (SCLC) devices. Strong co-facial interactions (π-π, SS) among TTA cores along with a high tendency of the derivative to align homeotropically in the columnar mesophase over a large area in SCLC cells

  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。