5,5'''-dibromo-3,3'''-didodecyl-2,2':5',2'':5'',2'''-quaterthiophene | 561068-09-5

• 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: 5,5'''-dibromo-3,3'''-didodecyl-2,2':5',2'':5'',2'''-quaterthiophene
• 英文别名: 2,2′-dibromo-3,3‴-didodecylquaterthiophene；5,5'''-dibromo-3,3'''-bis(dodecyl)-2,2':5',2'':5'',2'''-quarterthiophene；bis(5-(3-bromo-4-dodecyl))-(2,2')-bithiophene；5,5'-bis(5-bromo-3-n-dodecylthiophen-2-yl)-2,2'-bithiophene；5-Bromo-2-[5-[5-(5-bromo-3-dodecylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]-3-dodecylthiophene
• CAS: 561068-09-5
• 化学式: C₄₀H₅₆Br₂S₄
• 分子量: 824.957
• InChiKey: STQCOQSFXAZFHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.2
• 重原子数：
  46
• 可旋转键数：
  25
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  5,5'''-dibromo-3,3'''-didodecyl-2,2':5',2'':5'',2'''-quaterthiophene 、 4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)benzene boronic acid 在 四(三苯基膦)钯 碳酸氢钠 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 12.0h， 以81%的产率得到
  参考文献：
  名称：

  π共轭低聚噻吩的复杂液晶上层结构。

  摘要：

  DOI：

  10.1002/anie.200701585
• 作为产物：
  描述：

  5,5′-双(3-十二烷基-2-噻吩基)-2,2′-联噻吩 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以75%的产率得到5,5'''-dibromo-3,3'''-didodecyl-2,2':5',2'':5'',2'''-quaterthiophene
  参考文献：
  名称：

  新型聚噻吩衍生物的缺电子单元和叉指堆积形状对有机薄膜晶体管和光伏电池的影响

  摘要：

  通过斯蒂勒偶联反应成功地合成了一系列新的以噻唑环为电子缺陷单元的聚噻吩衍生物。根据由不同侧链构型引起的相互交叉的堆积结构，将合成的聚合物分为两类（H形堆积和A形堆积）。含有噻唑单元的噻吩衍生物（PT50Tz50，PTz100和PTTz）比完整的噻吩聚合物（PT100和PTT）表现出更好的热稳定性。包含噻唑单元的聚合物（PTz100和PTTz）显示出红移的吸收光谱，具有清晰的振子结构。此外，X射线衍射和原子力显微镜的结果表明，含有噻唑单元和相互交叉的H形的聚合物表现出比其他聚合物更好的有序和连接的分子间结构。改善的分子间有序性和表面形态直接促进了薄膜晶体管（TFT）器件中电荷载流子的传输，而没有引入电荷陷阱，并产生了更高的太阳能电池性能。在这些聚合物中，PTTz共聚物表现出最佳的TFT性能（μ= 0.050 cm 2 V -1 s -1，开/关比= 10 6，并且V th= -2 V）和太阳能电池性能（PCE

  DOI：

  10.1002/pola.24724

文献信息

• High performance semiconducting polymers containing bis(bithiophenyl dithienothiophene)-based repeating groups for organic thin film transistors
  作者：Kyung Hwan Kim、Dae Sung Chung、Chan Eon Park、Dong Hoon Choi

  DOI：10.1002/pola.24415

  日期：2011.1.1

  dithienothiophene‐containing conjugated polymers, such as poly(2,6‐bis(2‐thiophenyl‐3‐dodecylthiophene‐2‐yl)dithieno[3,2‐b;2′,3′‐d]thiophene, 4 and poly(2,6‐bis (2‐thiophenyl‐4‐dodecylthiophene‐2‐yl)dithieno[3,2‐b;2′,3′‐d]thiophene, 8 have been successfully synthesized via Stille coupling reactions using dodecyl‐substituted thiophene‐based monomers, bistributyltin dithienothiophene, and bistributyltin

  新型的含有二噻吩并噻吩的共轭聚合物，例如聚（2,6-双（2-噻吩基-3-十二烷基噻吩-2-基）二噻吩并[3,2-b; 2'，3'-d]噻吩，4和聚（2,6-双（2-噻吩基-4-十二烷基噻吩-2-基）二噻吩并[3,2-b; 2'，3'-d]噻吩，8已通过使用十二烷基取代的噻吩基单体，双三丁基锡二噻吩并噻吩和双三丁基锡联噻吩通过Stille偶联反应成功合成; 这些聚合物已被充分表征。两种聚合物之间的主要区别是重复基团中十二烷基侧链的取代位置。掠入射X射线衍射（GI-XRD）清楚地证明了多晶向基板的边缘定向。已经在有机薄膜晶体管（OTFT）中评估了这两种聚合物的半导体性能。两种共轭聚合物4和8表现出相当高的空穴载流子迁移率，高达μave = 0.05 cm 2 / Vs（I ON / OFF在热退火处理之后，分别为＝ 3.42×10 4）和μave＝ 0.01cm 2 / Vs（I ON / OFF＝
• ELECTRO-CHEMICAL SENSORS, SENSOR ARRAYS AND CIRCUITS
  申请人：The Johns Hopkins University

  公开号：US20130161599A1

  公开（公告）日：2013-06-27

  An electro-chemical sensor includes a first electrode, a second electrode spaced apart from the first electrode, and a semiconductor channel in electrical contact with the first and second electrodes. The semiconductor channel includes a trapping material. The trapping material reduces an ability of the semiconductor channel to conduct a current of charge carriers by trapping at least some of the charge carriers to localized regions within the semiconductor channel. The semiconductor channel includes at least a portion configured to be exposed to an analyte to be detected, and the trapping material, when exposed to the analyte, interacts with the analyte so as to at least partially restore the ability of the semiconductor channel to conduct the current of charge carriers.

  一种电化学传感器包括第一电极、与第一电极间隔的第二电极和与第一和第二电极电接触的半导体通道。半导体通道包括一个捕获材料，该捕获材料通过将至少一些电荷载体捕获到半导体通道内的局部区域来降低半导体通道导电载流子的能力。半导体通道包括至少一部分被配置为暴露于待检测的分析物，并且当暴露于分析物时，捕获材料与分析物相互作用，以至少部分恢复半导体通道导电载流子的能力。
• Polythiophenes and devices thereof
  申请人：Xerox Corporation

  公开号：EP1327646A1

  公开（公告）日：2003-07-16

  A polythiophene wherein the monomer segments thereof contain wherein A is a side chain; B is hydrogen or a side chain; and D is a divalent segment, and wherein the number of A-substituted thienylene units (I) in the monomer segments is from about 1 to about 10, the number of B-substituted thienylene units (II) is from 0 to about 5, and the number of divalent segments D is 0 or 1.

  一种聚噻吩，其单体段包含 其中 A 是侧链；B 是氢或侧链；D 是二价段，且单体段中 A 取代的噻吩单元 (I) 的数量约为 1 至约 10，B 取代的噻吩单元 (II) 的数量为 0 至约 5，二价段 D 的数量为 0 或 1。
• Tetrathiafulvalene (TTF)-Functionalized Thiophene Copolymerized with 3,3‴-Didodecylquaterthiophene: Synthesis, TTF Trapping Activity, and Response to Trinitrotoluene
  作者：Jasmine Sinha、Stephen J. Lee、Hoyoul Kong、Thomas W. Swift、Howard E. Katz

  DOI：10.1021/ma3019365

  日期：2013.2.12

  We report a synthesis route to a thiophene polymer where the repeat unit consists of 3,3'''-didodecylquaterthiophene (as in PQT12) plus an additional thiophene ring from which other functional groups may be projected. The hydroxymethyl form of this polymer, while only a poor semiconductor in its own right, serves as a vehicle for compatibilizing PQT12 itself with arbitrary functional groups. In this article, we focus on tetrathiafulvalene (TTF) as the functionality. As expected, the TTF group acts as a hole trap, as shown by loss of hole mobility and a surprising negative Seebeck coefficient, but this enables a current-increase response to trinitrotoluene as an analyte and confirms a similar observation we recently reported for a dissolved TTF. Added dopants also fill the trap states, restoring hole mobility and the typical positive Seebeck coefficient.
• Discrete Photopatternable π-Conjugated Oligomers for Electrochromic Devices
  作者：Christian B. Nielsen、Alex Angerhofer、Khalil A. Abboud、John R. Reynolds

  DOI：10.1021/ja7112273

  日期：2008.7.1

  Three discrete oligomeric systems including an all-thiophene (T6) system, a thiophene/phenylene (TPTTPT) system, and a thiophene/EDOT/phenylene (TPEEPT) system have been constructed and characterized with emphasis on structural, optical, electrochemical, and spectroelectrochemical properties. For all three chromophores, the radical cation, the dication, and the 7r-dimer have been identified and characterized. EPR spectroscopy reveals that the radical cations of TPTTPT and TPEEPT have g values of 2.008-2.012 and peak-to-peak widths in the range 4.2-5.3 G. Formation of the radical cation takes place at a lower potential for TPEEPT than for TPTTPT and T6, whereas subsequent oxidation to the dication occurs more easily for TPTTPT than for TPEEPT and T6. We ascribe this observation to more localized charges in the oxidized species of TPEEPT, which is supported by our finding that the radical cation of TPEEPT is less prone to undergo 7r-dimerization than the radical cations of TPTTPT and T6. All the oxidized species are sufficiently stable to allow for optical characterization, and the relative positions of all absorption bands are found to be in agreement with the electrochemical data. For further solid-state modifications of these materials, we have effectively modified the synthetic design and grafted terminal functionalities (e.s. acrylates) onto the discrete oligorners. Of these novel materials, TPEEPT proves to be the most promising anodically coloring material for electrochromics, and it undergoes reversible switching between two different colored states (bright yellow and clear blue) and one almost transparent and color neutral state. Contrast ratios, measured as 0%Tat Amax, are as high as 62.5%, and switching times are in the range 2-5 s for the coloration process, though significantly longer for the bleaching process. As a proof of concept, we have successfully constructed a simple photopatterned electrochromic device by exploiting the terminal acrylate functionalities of the oligomers in a UV-initiated cross-linking process. To the best of our knowledge, this is the first oligomer-based photopatterned electrochromic device reported in the literature.