6,7-bis(5-bromothien-2-yl)-6,7-di-n-hexyl-[1,2,5]thiadiazolo[3,4-g]quinoxaline | 1174457-26-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6,7-bis(5-bromothien-2-yl)-6,7-di-n-hexyl-[1,2,5]thiadiazolo[3,4-g]quinoxaline
• CAS: 1174457-26-1
• 化学式: C₂₈H₃₀Br₂N₄S₃
• 分子量: 678.579
• InChiKey: ZIAHKJVCQJZSLS-UHFFFAOYSA-N

物化性质

• 沸点：
  638.5±50.0 °C(Predicted)
• 密度：
  1.476±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.86
• 重原子数：
  37.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  51.56
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6,7-bis(5-bromothien-2-yl)-6,7-di-n-hexyl-[1,2,5]thiadiazolo[3,4-g]quinoxaline 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：

  6,7-di-n-hexyl-4,9-di(thien-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以76%的产率得到6,7-bis(5-bromothien-2-yl)-6,7-di-n-hexyl-[1,2,5]thiadiazolo[3,4-g]quinoxaline
  参考文献：
  名称：

  Dithienopyrrole-based donor–acceptor copolymers: low band-gap materials for charge transport, photovoltaics and electrochromism

  摘要：

  一系列高度可溶的供体-受体（D-A）共聚物，包含N-(3，4，5-三-n-十三烷氧基苯基)-二噻吩并[3，2-b:2'，3'-d]吡咯（DTP）或N-(2-癸基十四烷基)-二噻吩并[3，2-b:2'，3'-d]吡咯（DTP'）作为供体，三种不同受体，4，7-二噻吩-2-基-[2，1，3]-苯并噻二唑，4，9-二噻吩-2-基-6，7-二-n-己基-[1，2，5]噻二唑并[3，4-g]喹喔啉和4，8-二噻吩-2-基-2Λ4Δ2-苯并[1，2-c;4，5-c']双[1，2，5]噻二唑（BThX，X分别为BTD、TQHx2、BBT）通过Stille偶联聚合合成。研究了这些共聚物的光学和电化学性质，以及它们在场效应晶体管和光伏器件中的应用。从UV-vis-NIR光谱和电化学测量估算的带隙（eV）在约1.5至0.5 eV之间变化，并与使用密度泛函理论外推的量子化学估算一致。共聚物的氧化和还原光谱电化学表明它们可以进行p型和n型掺杂，通过电化学氧化或还原可以得到三到四种不同颜色的氧化还原状态。DTP-BThBTD和DTP-BThTQHx2共聚物表现出平均场效应空穴迁移率分别为1.2 × 10^-4和2.2 × 10^-3 cm2/(Vs)。DTP-BThBBT表现出双向场效应特性，空穴和电子迁移率分别为1.2 × 10^-3和5.8 × 10^-4 cm2/(Vs)。由这些共聚物与3'-苯基-3'H-环丙并[1，9](C60-Ih)[5，6]富勒烯-3'-丁酸甲酯（PCBM）（重量比1:3）混合制成的体异质结光伏器件在模拟辐照度75 mW/cm2下表现出高达1.3%的平均功率转换效率。

  DOI：

  10.1039/b915940a