4,4-di-p-tolyl-4H-indeno[1,2-b]thiophene | 881690-46-6

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 4,4-di-p-tolyl-4H-indeno[1,2-b]thiophene
• 英文别名: 8,8-di-p-tolyl-8H-3-thia-cyclopenta[a]indene；4,4-Bis(4-methylphenyl)indeno[1,2-b]thiophene
• CAS: 881690-46-6
• 化学式: C₂₅H₂₀S
• 分子量: 352.5
• InChiKey: LJIUPJBTRGYJKK-UHFFFAOYSA-N

物化性质

• 熔点：
  160-161 °C(Solv: hexane (110-54-3); chloroform (67-66-3))
• 沸点：
  470.4±14.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  26
• 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：

  4,4-di-p-tolyl-4H-indeno[1,2-b]thiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以68%的产率得到2-bromo-4,4-di-p-tolyl-4H-indeno[1,2-b]thiophene
  参考文献：
  名称：

  Quaterthiophenes with Terminal Indeno[1,2-b]thiophene Units as p-Type Organic Semiconductors

  摘要：

  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.

  DOI：

  10.1021/jo802028n
• 作为产物：
  描述：

  2-碘苯甲酸乙酯, 在 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 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

• Lewis Acid Mediated One-Pot Synthesis of Aryl/Heteroaryl-Fused Carbazoles Involving a Cascade Friedel-Crafts Alkylation/Electrocyclization/Aromatization Reaction Sequence
  作者：Radhakrishnan Sureshbabu、Velu Saravanan、Vasudevan Dhayalan、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.201001309

  日期：2011.2

  ]-fused carbazoles has been developed startingfrom suitably substituted 2/3-(bromomethyl)indoles and ar-enes under Lewis acid catalysis. The attractive feature ofthis protocol is the fact that a wide variety of π-conjugatedannulated carbazoles can be readily accessed by the appro-priate choice of arenes and heteroarenes. The annulationprotocol has been extended to (bromomethyl)benzene aswell as 2,

  在路易斯酸催化下，以适当取代的 2/3-（溴甲基）吲哚和芳烯为原料开发了]-稠合咔唑。本协议的有吸引力的特征是，可以通过竞争和杂种丁烯的应用选择可以容易地访问各种π缀合的咔唑。环化协议已扩展到（溴甲基）苯以及 2,5-双（溴甲基）噻吩。发现吲哚基-2-甲基乙酸酯的环化不如相应的2-(溴甲基)吲哚合适。然而，在苄体系的情况下，发现相应的醋酸盐更适用。在这项工作中开发的路易斯酸介导的级联环化序列可能会导致在多环芳香杂环领域的新应用。
• Supramolecular aggregation for manipulating molecular packing by endgroups leading to mechanochromic fluorescence
  作者：Jian Cao、Hua-Chun Wang、Xiancheng Ren、Yun-Xiang Xu

  DOI：10.1016/j.dyepig.2021.109668

  日期：2021.11

  Herein, ladder-type molecules based on planar indeno[1,2-b]thiophene 1,1-dioxides (ITDO) backbones are designed. The moderate dipole moment originating from the donor-acceptor structure of backbone and steric sidechains leads to a loose supramolecular aggregation with dimeric structures. And the emission properties could be tuned by introducing halogen endgroups onto the backbones. As a result, ITDO-Cl

  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，