2,5-bis(5-bromo-3-dodecylthiophen-2-yl)thieno[3,2-b]thiophene | 1170871-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 2,5-bis(5-bromo-3-dodecylthiophen-2-yl)thieno[3,2-b]thiophene
• CAS: 1170871-55-2
• 化学式: C₃₈H₅₄Br₂S₄
• 分子量: 798.919
• InChiKey: AINSKTNJWDSLKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.9
• 重原子数：
  44
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 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：

  2,5-bis(5-bromo-3-dodecylthiophen-2-yl)thieno[3,2-b]thiophene 、 在 四(三苯基膦)钯 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 水 为溶剂， 反应 25.0h， 以40%的产率得到
  参考文献：
  名称：

  Synthesis and characterization of oligo(2,5-bis(3-dodecylthiophen-2-yl)thieno[3,2-b]thiophene)s: effect of the chain length and end-groups on their optical and charge transport properties

  摘要：

  研究人员合成了分别具有 H 和 CN 端基的寡(2,5-双(3-十二烷基噻吩-2-基)噻吩并[3,2-b]噻吩)Tn 和 Tn-2CN（n = 4、8、12、20，n 代表噻吩环数），并研究了链长和端基对其性质的影响。对于 Tn 和 Tn-2CN 来说，随着链长的增加，吸收光谱会发生红移。在较短的低聚物（n = 4 和 8）中，引入抽电子的 CN 端基可导致溶液和薄膜状态下的吸收光谱发生显著的红移。然而，对于 n = 12 和 20 的低聚物，只有在薄膜状态下才能观察到明显的吸收光谱红移。通过引入 CN 端基，最高占位分子轨道（HOMO）和最低未占位分子轨道（LUMO）能级都降低了，而且降低程度随着链长的增加而降低。二维掠入射 X 射线衍射（2D-GIXD）和原子力显微镜（AFM）研究表明，链长和末端基团都会影响低聚物的薄膜微观结构。n = 4 和 n = 8 的低聚物以倾斜角度立在基底上，T4-2CN 和 T8-2CN 的薄膜具有三维晶体结构。与此相反，n=12 和 20 的低聚物采用边缘排列，分子长轴平行于基底，就像聚合物一样。与 T12 和 T20 薄膜相比，T12-2CN 和 T20-2CN 薄膜的晶体区域更大，与基底的取向性更强，片层距离更短。低聚物的电荷传输特性受到链长和端基的影响，因为它们对薄膜的形态和堆积结构有显著的影响。T8-2CN 薄膜结合了三个特征：畴尺寸大、表面通透度低和晶界减少，因此表现出最高的场效应迁移率。

  DOI：

  10.1039/c4tc01899k
• 作为产物：
  描述：

  2-溴-3-十二烷基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 2,5-bis(5-bromo-3-dodecylthiophen-2-yl)thieno[3,2-b]thiophene
  参考文献：
  名称：

  Synthesis and characterization of oligo(2,5-bis(3-dodecylthiophen-2-yl)thieno[3,2-b]thiophene)s: effect of the chain length and end-groups on their optical and charge transport properties

  摘要：

  研究人员合成了分别具有 H 和 CN 端基的寡(2,5-双(3-十二烷基噻吩-2-基)噻吩并[3,2-b]噻吩)Tn 和 Tn-2CN（n = 4、8、12、20，n 代表噻吩环数），并研究了链长和端基对其性质的影响。对于 Tn 和 Tn-2CN 来说，随着链长的增加，吸收光谱会发生红移。在较短的低聚物（n = 4 和 8）中，引入抽电子的 CN 端基可导致溶液和薄膜状态下的吸收光谱发生显著的红移。然而，对于 n = 12 和 20 的低聚物，只有在薄膜状态下才能观察到明显的吸收光谱红移。通过引入 CN 端基，最高占位分子轨道（HOMO）和最低未占位分子轨道（LUMO）能级都降低了，而且降低程度随着链长的增加而降低。二维掠入射 X 射线衍射（2D-GIXD）和原子力显微镜（AFM）研究表明，链长和末端基团都会影响低聚物的薄膜微观结构。n = 4 和 n = 8 的低聚物以倾斜角度立在基底上，T4-2CN 和 T8-2CN 的薄膜具有三维晶体结构。与此相反，n=12 和 20 的低聚物采用边缘排列，分子长轴平行于基底，就像聚合物一样。与 T12 和 T20 薄膜相比，T12-2CN 和 T20-2CN 薄膜的晶体区域更大，与基底的取向性更强，片层距离更短。低聚物的电荷传输特性受到链长和端基的影响，因为它们对薄膜的形态和堆积结构有显著的影响。T8-2CN 薄膜结合了三个特征：畴尺寸大、表面通透度低和晶界减少，因此表现出最高的场效应迁移率。

  DOI：

  10.1039/c4tc01899k

文献信息

• Thieno[3,2-b]thiophene oligomers and their applications as p-type organic semiconductors
  作者：Moawia O. Ahmed、Chunmei Wang、Peisi Keg、Wojciech Pisula、Yeng-Meng Lam、Beng S. Ong、Siu-Choon Ng、Zhi-Kuan Chen、Subodh G. Mhaisalkar

  DOI：10.1039/b900979e

  日期：——

  This study describes the synthesis, characterization and electronic properties of a novel series of soluble thieno[3,2-b]thiophene oligomers (1a and b and 2a and b) for thin film transistor (TFT) applications. All the compounds were synthesized in high yield using Pd-catalyzed Stille or Suzuki coupling reactions and were substituted by two dodecyl groups at the 3- or 4-position of the thiophene unit to ensure the solubility for facile device fabrication. Aryl units such as phenyl and naphthyl were used for ‘end-capping’ to provide stability against oxidation. The design of these materials has focused on their self-assembly and solution processability. All the compounds have been characterized by 1H, 13C NMR, and elemental analysis. Their electronic and optical properties were investigated using UV-Vis and photoluminescence spectroscopy, cyclic voltammetry, thermal gravimetric analysis (TGA), and differential scanning calorimetry (DSC). High-resolution STM images of 1a and 2a adsorbed on HOPG revealed highly ordered self-organized domains. Two-dimensional wide-angle X-ray scattering (2D-WAXS) was used to study the solid state packing of 1a and 2a. Top-contact OTFT devices from 1a were prepared by spin coating and showed promising behaviour with mobilities up to 3.11 × 10−2 cm2V−1 s−1 and on/off ratios up to 104.

  本研究描述了薄膜晶体管（TFT）应用中一系列新型可溶性噻吩[3,2-b]噻吩低聚物（1a和b以及2a和b）的合成、表征和电子特性。所有化合物均采用钯催化的斯蒂尔或铃木偶联反应合成，并在噻吩单元的3或4位上被两个十二烷基取代，以确保在简易器件制造中的可溶性。苯基和萘基等芳基单元用于“端封”，以提供抗氧化稳定性。这些材料的设计侧重于其自组装和溶液可加工性。所有化合物均通过1H、13C NMR和元素分析进行了表征。利用紫外-可见光和光致发光光谱、循环伏安法、热重分析（TGA）和差示扫描量热法（DSC）研究了它们的电子和光学特性。吸附在HOPG上的1a和2a的高分辨率STM图像揭示了高度有序的自组织域。二维广角X射线散射（2D-WAXS）用于研究1a和2a的固态堆积。通过旋涂制备了1a的顶部接触OTFT器件，并显示出良好的性能，迁移率高达3.11×10-2 cm2V-1 s-1，开/关比高达104。
• Design and synthesis of proton-dopable organic semiconductors
  作者：Chenzhu Yin、Masakazu Mukaida、Shohei Horike、Kazuhiro Kirihara、Shogo Yamane、Zhenya Zhang、Qingshuo Wei

  DOI：10.1039/d2ra00216g

  日期：——

  doped by protonic acid in both solution and solid-state, resulting in a broad absorption in the near-infrared range corresponding to polaron and bipolaron absorption. Electrical conductivity of ca. 0.1 S cm−1 was obtained at 100 °C (to avoid the water uptake by the acid). The adducts with protons bound at the end-thiophene α-position were confirmed by 1H Nuclear Magnetic Resonance spectra.

  本文展示了如何使用质子化的 3,4-乙烯二氧噻吩部分作为端基来制造有机导体。有机半导体 2,5-双(5-(2,3-二氢噻吩并[3,4 -b ][1,4]二恶英-5-基)-3-十二烷基噻吩-2-基)噻吩并[3,2- b ]噻吩的设计和合成。该分子可以在溶液和固态中掺杂质子酸，从而在近红外范围内产生与极化子和双极化子吸收相对应的广泛吸收。电导率约在100℃下获得0.1Scm -1 （以避免酸吸收水）。通过1 H 核磁共振波谱证实了在噻吩末端 α 位结合质子的加合物。
• The Good Host: Formation of Discrete One-Dimensional Fullerene “Channels” in Well-Ordered Poly(2,5-bis(3-alkylthiophen-2-yl)thieno[3,2-<i>b</i>]thiophene) Oligomers
  作者：Lei Zhang、Feng Liu、Ying Diao、Hilary S. Marsh、Nicholas S. Colella、Arthi Jayaraman、Thomas P. Russell、Stefan C. B. Mannsfeld、Alejandro L. Briseno

  DOI：10.1021/ja510976n

  日期：2014.12.31

  Due to the unique crystallinity of poly(2,5-bis(3-alkylthiophen-2-yl)thieno[3,2-b]thiophene) (PBTTT), it is an excellent model polymer to study the structureproperty relationship in organic devices, especially those relying on junctions of electron- and hole-transporting materials. Here, we report the synthesis and characterization of a series of monodisperse PBTTT oligothiophenes (n = 15) and systematically examine the evolution of crystalline behavior, morphology, and interaction with [6,6]-phenyl C-61-butyric acid methyl ester (PCBM) as the molecular conjugation length increases. We discovered that fullerene intercalation occurs when there is enough free volume between the side chains to accommodate the fullerene molecule. The intercalation of PCBM is observed beyond BTTT-2 and longer oligomers, likely similar to that of PBTTT. Interestingly, both experiments and molecular simulations show that PCBM intercalation also appears to catalyze a more efficient packing of the BTTT-2 dimers. Crystal structure analysis revealed that the straight BTTT-2 side chains form one-dimensional (1D) channels that could perfectly host PCBM but, in the pure material, accommodate the interdigitated side chains from adjacent layers. In the blend with PCBM, these channels are maintained and enable the cocrystallization and intercalation of PCBM. This is the first time the actual sublattice cell of PCBM has been determined from the X-ray data, and demonstration the utility of the oligomers as model systems for their polymer counterparts. Among the organic photovoltaic devices (OPVs) made from the BTTT oligomers and [6,6]-phenyl C(71-)butyric acid methyl ester (PC71BM) blends, the ones containing the BTTT-2 dimer exhibit the highest performance.
• THIENOTHIOPHENE DERIVATIVES
  申请人：Moawia Omer E. Ahmed

  公开号：US20100331550A1

  公开（公告）日：2010-12-30

  An organic compound represented by the following general formula (I) and characterised by the conjugation of thieno[3,2-b]thiophene, thiophene and phenylene units in the conjugated compound.
• US8329915B2
  申请人：——

  公开号：US8329915B2

  公开（公告）日：2012-12-11