2-bromo-4,4-di-p-tolyl-4H-indeno[1,2-b]thiophene | 881690-47-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-bromo-4,4-di-p-tolyl-4H-indeno[1,2-b]thiophene
• 英文别名: 2-bromo-8,8-di-p-tolyl-8H-3-thia-cyclopenta[a]indene；2-Bromo-4,4-bis(4-methylphenyl)indeno[1,2-b]thiophene
• CAS: 881690-47-7
• 化学式: C₂₅H₁₉BrS
• 分子量: 431.396
• InChiKey: NQZMILKTJPLYQD-UHFFFAOYSA-N

物化性质

• 沸点：
  505.1±38.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-4,4-di-p-tolyl-4H-indeno[1,2-b]thiophene 在 Oxone 、 碳酸氢钠 作用下， 以 氯仿 、 水 、 丙酮 为溶剂， 反应 48.0h， 以37%的产率得到
  参考文献：
  名称：

  通过端基操纵分子堆积的超分子聚集导致机械变色荧光

  摘要：

  机械致变色荧光（MCF）材料在许多领域显示出巨大的潜力。但是合理设计合适的分子结构并调整其分子堆积和MCF特性仍然是一个巨大的挑战，特别是对于具有平面主链的分子。在此，设计了基于平面茚并 [1,2-b] 噻吩 1,1-二氧化物 (ITDO) 骨架的梯型分子。源自主链和空间侧链的供体-受体结构的中等偶极矩导致具有二聚体结构的松散超分子聚集。并且可以通过在主链上引入卤素端基来调整发射特性。结果，ITDO-Cl 和 ITDO-Br 表现出更强的分子间相互作用，导致双发射带和 MCF 特性。相比之下，

  DOI：

  10.1016/j.dyepig.2021.109668
• 作为产物：
  描述：

  2-噻吩-2-基苯甲酸乙酯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-bromo-4,4-di-p-tolyl-4H-indeno[1,2-b]thiophene
  参考文献：
  名称：

  Modulation of Physical Properties of Ter(9,9-ditolylfluorene) by Backbone-Embedded Heteroarenes

  摘要：

  Novel ter(9,9-ditolylfluorene) analogues containing thiophene and pyridine rings embedded as functional constituents within the parent hydrocarbon backbone have been synthesized. These new molecules exhibit highly efficient photoluminescence and high thermal and morphological stability. The electronic structure of the terfluorene backbone is significantly perturbed, which allows modulation of the backbone energy levels.

  DOI：

  10.1021/ol060183f

文献信息

• Quaterthiophenes with Terminal Indeno[1,2-<i>b</i>]thiophene Units as <i>p</i>-Type Organic Semiconductors
  作者：Laurent Pouchain、Olivier Alévêque、Yohann Nicolas、Agathe Oger、Charles-Henri Le Régent、Magali Allain、Philippe Blanchard、Jean Roncali

  DOI：10.1021/jo802028n

  日期：2009.2.6

  Quaterthiophenes 4T, Oct-4T, and Tol-4T based on a central 2,2'-bithiophene core alpha,omega,-terminated with 4,4-unsubstituted and 4,4-disubstituted n-octyl or p-tolyl indeno[1,2-b]thiophene have been synthesized by Stille or Miyaura-Suzuki couplings. Compound 4T was also synthesized by an alternative route involving a soluble precursor bearing solubilizing trimethylsilyl groups which have been eliminated in the last step. The electronic properties of the compounds have been analyzed by cyclic voltammetry, UV-vis absorption and fluorescence emission spectroscopy. Thermal evaporation of 4T and Oct-4T leads to crystalline thin films and UV-vis absorption and X-ray diffraction data for these films suggest that the molecules adopt a quasi-vertical orientation onto the substrate. Strong pi-pi intermolecular interactions have been observed for 4T but not for molecules Oct-4T due to the presence of n-octyl chains. Sublimed thin films of Tol-4T show an amorphous character. The characterization of field-effect transistors fabricated from these three materials gave a hole-mobility of 2.2 x 10(-2) cm(2) V-1 s(-1) with an on/off ratio of 2.2 x 10(4) for 4T while no field-effect was observed for Oct-4T and Tol-4T.
• Structural effects on the hole mobilities of indenothiophene-embedded homologs
  作者：Teng-Chih Chao、Ken-Tsung Wong、Wen-Yi Hung、Tei-Hung Hou、Wei-Jiun Chen

  DOI：10.1016/j.tetlet.2009.02.148

  日期：2009.7

  A systematic study of the relationship between the structures and the non-dispersive hole mobilities (Lip to 10(-3) cm(2) V-1 s(-1)) of a homologous series of amorphous indenothiophene-containing materials is described. The hole mobilities were dependent mainly on the length and rigidity of the pi-conjugated backbone and the peripheral substituents. (C) 2009 Elsevier Ltd. All rights reserved.