4,7-di-(5-bromo-3,4-ethylenedioxythiophene-2-yl)-2,1,3-benzothiadiazole | 900531-86-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 4,7-di-(5-bromo-3,4-ethylenedioxythiophene-2-yl)-2,1,3-benzothiadiazole
• 英文别名: 4,7-bis(7-bromo-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)benzo[c][1,2,5]thiadiazole；4,7-Bis(5-bromo-2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl)-2,1,3-benzothiadiazole
• CAS: 900531-86-4
• 化学式: C₁₈H₁₀Br₂N₂O₄S₃
• 分子量: 574.294
• InChiKey: JSQAJVUNDRIABE-UHFFFAOYSA-N

物化性质

• 沸点：
  660.3±55.0 °C(Predicted)
• 密度：
  1.919±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4,7-di-(5-bromo-3,4-ethylenedioxythiophene-2-yl)-2,1,3-benzothiadiazole 、 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Donor–Acceptor–Donor-based π-Conjugated Oligomers for Nonlinear Optics and Near-IR Emission

  摘要：

  A family of multi-heterocycle donor acceptor donor (DAD) telechelic conjugated oligomers designed for two-photon absorption (2PA) and emission in the near-infrared (near-IR) were prepared, and the relationship between their spectral, structural, and electrochemical properties were investigated. These oligomers, based on electron-rich thiophene, phenylene, and 3,4-ethylenedioxythiophene (EDOT) units as donors along with electron-deficient benzothiadiazole or its derivative units as acceptors, have been characterized through linear absorbance and fluorescence measurements, nonlinear absorbance, cyclic voltammetry, and differential pulse voltammetry to demonstrate the evolution of narrow HOMO-LUMO gaps ranging from 1.05 to 1.95 eV, with the oligomers composed of EDOT and benzo[1,2-c,3,4-c']bis[1,2,5]thiadiazole (BBT) exhibiting the narrowest gap. The absorption maxima ranges from 517 to 846 nm and the fluorescence maxima ranges from 651 to 1088 nm for the different oligomers. Z-scan and two-photon fluorescence were used to measure the frequency degenerate 2PA of the different oligomers. The oligomer's 2PA cross sections ranged from 900-3500 GM, with the oligomer containing EDOT donor units and a BBT acceptor unit exhibiting the largest 2PA cross section. The use of these oligomers in red to near-IR emitting polymer light-emitting diodes (PLEDs) was demonstrated by blending the soluble emitting oligomers into a suitable host matrix. Energy transfer from the matrix to the emitting oligomer can be achieved, resulting in PLEDs with pure oligomer emission.

  DOI：

  10.1021/cm201424a
• 作为产物：
  描述：

  2,1,3-苯并噻二唑 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 氢溴酸 、 溴 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.0h， 生成 4,7-di-(5-bromo-3,4-ethylenedioxythiophene-2-yl)-2,1,3-benzothiadiazole
  参考文献：
  名称：

  新型基于乙二氧基噻吩的共轭聚合物的电致变色器件和薄膜晶体管† ‡

  摘要：

  基于EDOT的新型电致变色共轭聚合物及其相应器件（乙二氧基噻吩）进行了说明。这些聚合物中最好的聚合物在可见光和近红外（Vis-NIR）光谱区域中显示大约1s的响应时间和高可切换对比度。这些新聚合物的薄膜（70 nm）表现出的光学带隙为1.73 eV（7a）<2.19 eV（7b）<2.23 eV（7c）<2.31 eV（4）<2.34 eV（2）它们对吸收边缘的外推。聚合物4和7a显示出约1的场效应空穴迁移率。6.7×10 -5 cm 2 V -1 s -1（开/关比10 4）和2.5×10-5 cm 2 V -1 s -1（开/关比10 3）分别与它们的高度有序的链间堆积有关，如通过聚合物4的XRD分析所证实的。电致变色表征表明，聚合物7a-c在低压下在红外中表现出明显的吸收变化。最终的固态器件有望为IR中的电致变色快门和滤光片提供希望，因为它们的高电荷转移迁移率和离子注入效率允许相对快

  DOI：

  10.1039/c0nj00837k

文献信息

• 一种低能隙宽吸收的共轭聚合物及其制备方法
  申请人：常州大学

  公开号：CN103923106B

  公开（公告）日：2016-08-24

  本发明涉及有机半导体制备技术领域，具体为一种可应用于太阳能电池的低能隙宽吸收的共轭单体聚合物及其制备方法，本发明的技术方案是以3，4‑乙撑二氧基噻吩(EDOT)为供电子单元，2，1，3苯并噻二唑(BT)为受电子单元，采用Heck偶合反应由EDOT与BT得到新型D‑A型共轭单体EDOTBT，该共轭单体具有较强的电子推拉效应，通过Heck偶合反应或者Suzuki偶合反应可由上述D‑A型共轭单体制备高分子量新型聚合物，这些聚合物具有低带隙、宽吸收、较高的光转化效率及良好的成膜性的特点，可用做聚合物太阳能电池的活性层，可有效提高聚合物太阳能电池的能量转换效率，适宜在聚合物太阳能电池中推广应用。
• Organic dyes end-capped with perfluorophenyl anchors: Synthesis, electrochemical properties and assessment of sensitization capacity of titania photoanodes
  作者：Panagiotis Giannopoulos、Dimitrios Raptis、Krystallia Theodosiou、Aikaterini K. Andreopoulou、Charalampos Anastasopoulos、Alexandros Dokouzis、George Leftheriotis、Panagiotis Lianos、Joannis K. Kallitsis

  DOI：10.1016/j.dyepig.2017.09.007

  日期：2018.1

  In the present work, organic sensitizers are synthesized and attached on TiO2 photoanodes via Ti-O-C bonds. All sensitizers, designed for this purpose are symmetrical and have two perfluorophenyl end groups, which can lead to stable non-hydrolysable bonds on the TiO2 surface. Broad absorption in the UV Vis region and low band gap energy levels have been achieved through the alternation of carbazoleand benzothiadiazole-based units. All dyes and their corresponding photoanodes, were characterized via various complementary techniques, including Cyclic Voltammetry measurements and sensitization capacity in Dye-sensitized solar cell tests. (C) 2017 Elsevier Ltd. All rights reserved.
• GREEN TO TRANSMISSIVE SOLUBLE ELCTROCHROMIC POLYMERS
  申请人：University of Florida Research Foundation, Inc.

  公开号：EP2209830B1

  公开（公告）日：2016-06-29
• GREEN TO TRANSMISSIVE SOLUBLE ELECTROCHROMIC POLYMERS
  申请人：Beaujuge Pierre Marc

  公开号：US20100298527A1

  公开（公告）日：2010-11-25

  Green to transmissive soluble electrochromic polymers are conjugated polymers having a plurality of repeating units where repeating units are a plurality of substituted dioxyheterocycle based donor groups coupled to an acceptor group. The conjugated polymer absorbs radiation within a first band of the visible spectrum and a second band of the visible spectrum when in a neutral state resulting in a green color and is transmissive when in an oxidized state. The polymers are soluble allowing processing of films and coatings from solution.
• US8383761B2
  申请人：——

  公开号：US8383761B2

  公开（公告）日：2013-02-26