(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）。
• Twisted but Conjugated: Building Blocks for Low Bandgap Polymers
  作者：Chien-Yang Chiu、Hengbin Wang、Fulvio G. Brunetti、Fred Wudl、Craig J. Hawker

  DOI：10.1002/anie.201400674

  日期：2014.4.7

  Here we report a novel twisted monomer based on a distorted CC double bond for low bandgap conjugated copolymers. This new building block provides several unique characteristics when compared to classical planar systems such as high solubility, electron accepting ability, and isomeric tunability. The resulting copolymers exhibit broad absorption spanning both visible and near‐infrared regions leading

  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。
• 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.