(E)-8,8'-biindeno[2,1-b]thiophenylidene | 38056-16-5

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: (E)-8,8'-biindeno[2,1-b]thiophenylidene
• 英文别名: (4E)-4-indeno[2,1-b]thiophen-4-ylideneindeno[2,1-b]thiophene
• CAS: 38056-16-5
• 化学式: C₂₂H₁₂S₂
• 分子量: 340.469
• InChiKey: CZUUIWPWZNRIDB-FMQUCBEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-8,8'-biindeno[2,1-b]thiophenylidene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(E)-2,2′-dibromo-8,8′-biindeno[2,1-b]thiophenylidene
  参考文献：
  名称：

  扭曲但共轭：低带隙聚合物的构建基块

  摘要：

  在这里，我们报告了一种基于扭曲的CC双键的新型扭曲单体，用于低带隙共轭共聚物。与传统的平面系统相比，这种新的构建基块具有几个独特的特性，例如高溶解度，电子接受能力和异构体可调性。所得的共聚物在可见光和近红外区域均表现出广泛的吸收性，从而带来了令人鼓舞的太阳能电池性能。

  DOI：

  10.1002/anie.201400674
• 作为产物：
  描述：

  2-噻吩-3-基苯甲酸 在 劳森试剂 、 aluminum (III) chloride 、 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.0h， 生成 (E)-8,8'-biindeno[2,1-b]thiophenylidene
  参考文献：
  名称：

  扭曲但共轭：低带隙聚合物的构建基块

  摘要：

  在这里，我们报告了一种基于扭曲的CC双键的新型扭曲单体，用于低带隙共轭共聚物。与传统的平面系统相比，这种新的构建基块具有几个独特的特性，例如高溶解度，电子接受能力和异构体可调性。所得的共聚物在可见光和近红外区域均表现出广泛的吸收性，从而带来了令人鼓舞的太阳能电池性能。

  DOI：

  10.1002/anie.201400674

文献信息

• BUILDING BLOCK FOR LOW BANDGAP CONJUGATED POLYMERS
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20150194608A1

  公开（公告）日：2015-07-09

  A twisted but conjugated building block for low bandgap conjugated polymers. An organic device comprising a (E)-8,8′-biindeno[2,1-b]thiophenylidene (tBTP) based polymer.

  一种用于低带隙共轭聚合物的扭曲但共轭的构建模块。一种有机器件，包括基于(E)-8,8'-双吲哚[2,1-b]噻吩基的聚合物（tBTP）。
• Synthesis, Characterization, and Field-Effect Transistors Properties of Novel Copolymers Incorporating Nonplanar Biindeno[2,1-<i>b</i>]thiophenylidene Building Blocks
  作者：Chao Li、Zupan Mao、Huajie Chen、Liping Zheng、Jianyao Huang、Bin Zhao、Songting Tan、Gui Yu

  DOI：10.1021/acs.macromol.5b00067

  日期：2015.4.28

  A nonplanar but conjugated heteroacene, biindeno[2,1-b]thiophenylidene (BTP), is employed to design and synthesize solution-processable polymer semiconductors for organic field-effect transistors (OFETs) applications first. By copolymerizing with isoindigo (IDG), diketopyrrolopyrrole (DPP), and naphthalenediimide (NDI) derivatives, three novel BTP-based copolymers (PBTP-IDG, PBTP-DPP, and PBTP-NDI) have been synthesized and characterized successfully. The results indicate that three BTP-based polymers exhibit broad absorption spectra and good solubility in most common solvents. Because of the dominantly electron-deficient contributions to the whole polymer backbones, the energy levels of the lowest unoccupied molecular orbitals are decreased to ca. -4.0 eV for all these polymers, thus exhibiting good electron affinities. Moreover, the deep-lying energy levels of the highest occupied molecular orbitals (HOMO) have been demonstrated for three BTP-based polymers, with the HOMO values ranging from -5.48 to -5.80 eV. Investigation of the OFETs performance indicates that three BTP-based polymers exhibit well hole transport properties in ambient air and excellent ambipolar performance in a N-2 glovebox. Compared with PBTP-IDG and PBTP-NDI, the uniform morphological structure, interconnected polycrystalline grain, and close pi-pi stacking distance endow PBTP-DPP with higher hole mobility of 1.43 cm(2) V-1 s(-1). Particularly, the well-balanced hole and electron mobilities of 0.68 and 0.13 cm(2) V-1 s(-1) have been demonstrated for the PBTP-DPP-based OFETs in a N-2 atmosphere, respectively. The results suggest that the nonplanar BTP unit and its derivatives are promising p-conjugated building blocks for the design and synthesis of solution-processable polymer semiconductors with high charge-transporting performance.