4,7-diselenophen-2'-yl-2,1,3-benzothiadiazole | 711026-53-8

• 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-diselenophen-2'-yl-2,1,3-benzothiadiazole
• 英文别名: 4,7-di(2'-selenienyl)-2,1,3-benzothiadiazole；4,7-di(selenophen-2 -yl)benzo[c][1,2,5]-thiadiazole；4,7-di(selenophene-2-yl)benzo[c][1,2,5]thiadiazole；4,7-Diselenophene-2-yl-2,1,3-benzothiadiazole；4,7-di(selenophen-2-yl)-2,1,3-benzothiadiazole
• CAS: 711026-53-8
• 化学式: C₁₄H₈N₂SSe₂
• 分子量: 394.217
• InChiKey: WKDPDTIBNWGAIG-UHFFFAOYSA-N

物化性质

• 熔点：
  131-135 °C(Solvent: Ethanol ; Toluene)
• 沸点：
  533.8±40.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,7-diselenophen-2'-yl-2,1,3-benzothiadiazole 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 4,7-bis(5'-bromo-2'-selenophenyl)-2,1,3-benzoselenadiazole
  参考文献：
  名称：

  深红色电致发光聚合物：用于发光二极管和光伏器件的新型低带隙共轭共聚物的合成与表征

  摘要：

  一系列新的半导体共轭共聚物，衍生自烷基取代的芴，4,7-二硒酚-2'-yl-2,1,3-苯并噻二唑（SeBT）和4,7-二硒酚-2'-yl-2通过钯催化的Suzuki偶联反应，以不同的进料比合成1,3,3-苯并硒二唑（SeBSe）。共聚物的光学带隙非常低，对于SeBT为1.87 eV，对于SeBSe为1.77 eV。观察到从芴链段到窄带隙位点的有效快速能量转移。光致发光和电致发光的发射主要由窄带隙物质控制，并在670-790 nm处达到峰值，范围从深红色到近红外（NIR）。对于这两种类型的共聚物，器件的外部电致发光（EL）量子效率分别达到1.1％和0.3％。61丁酸甲酯（PCBM）作为活性层显示出令人鼓舞的性能。在AM1.5太阳模拟器下（78.2 mW / cm 2），能量转换效率（ECE）高达1％。对于来自PFO-SeBT和PFO-SeBSe的PPVC，光谱响应分别扩展到675和750 nm。

  DOI：

  10.1021/ma047969i
• 作为产物：
  描述：

  2,1,3-苯并噻二唑 在 bis-triphenylphosphine-palladium(II) chloride 、 氢溴酸 、 溴 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 生成 4,7-diselenophen-2'-yl-2,1,3-benzothiadiazole
  参考文献：
  名称：

  深红色电致发光聚合物：用于发光二极管和光伏器件的新型低带隙共轭共聚物的合成与表征

  摘要：

  一系列新的半导体共轭共聚物，衍生自烷基取代的芴，4,7-二硒酚-2'-yl-2,1,3-苯并噻二唑（SeBT）和4,7-二硒酚-2'-yl-2通过钯催化的Suzuki偶联反应，以不同的进料比合成1,3,3-苯并硒二唑（SeBSe）。共聚物的光学带隙非常低，对于SeBT为1.87 eV，对于SeBSe为1.77 eV。观察到从芴链段到窄带隙位点的有效快速能量转移。光致发光和电致发光的发射主要由窄带隙物质控制，并在670-790 nm处达到峰值，范围从深红色到近红外（NIR）。对于这两种类型的共聚物，器件的外部电致发光（EL）量子效率分别达到1.1％和0.3％。61丁酸甲酯（PCBM）作为活性层显示出令人鼓舞的性能。在AM1.5太阳模拟器下（78.2 mW / cm 2），能量转换效率（ECE）高达1％。对于来自PFO-SeBT和PFO-SeBSe的PPVC，光谱响应分别扩展到675和750 nm。

  DOI：

  10.1021/ma047969i

文献信息

• A Selenophene Analogue of PCDTBT: Selective Fine-Tuning of LUMO to Lower of the Bandgap for Efficient Polymer Solar Cells
  作者：Boram Kim、Hye Rim Yeom、Myoung Hee Yun、Jin Young Kim、Changduk Yang

  DOI：10.1021/ma302133h

  日期：2012.11.13

  In an attempt to further improve the performance of the PCDTBT-based polymer Solar cells (PSCs), we have synthesized a selenophene. analogue of PCDTBT, namely, PCDSeBT, in which diselenienylbenzothiadiazole (DSeBT) monomer alternately flanks with a 2,7-carbazole unit. The intrinsic properties of PCDSeBT are not only characterized by UV-vis absorption, cyclic voltammetry (CV), and organic field-effect transistors (OFETs) but also the surface morphology, mobilities of space charge-limited current (SCLC) model, and polymer solar cells (PSCs) in its bulk-heterojunction (BHJ) active layer with [6,6]-phenyl C-71-butyric acid methyl ester (PC71BM) are evaluated in detail. It is found that PCDSeBT simultaneously has a low-lying highest occupied molecular orbital (HOMO) energy level at -5.4 eV and a low bandgap of 130 eV as required by the ideal polymers for BHJ PSCs. The high current of 11.7 mA/cm(2) is obtained for PCDSeBT-based PSCs, to our knowledge, which is among, the highest short-circuit current density (J(SC)) values obtained from a BIT device consisting of PCDTBT derivatives and [6,6] phenyl C-61-butyric acid methyl ester (PCBM). The high J(SC) value, along with moderate fill factor (FP) of 45% and a high open circuit voltage (V-OC) of 079 V, yields a power conversion efficiency (PCE) of 4:12%, which is about 37% increase in PCE from a PCDTBT-based reference device. On the basis of our results, one can be concluded that the DSeBT placement for construction of donor (D) acceptor (A) polymers is an easy and effective way to realize both the higher J(SC) and V-OC values in PSCs, as a consequence of the selective lower-lying lowest unoccupied molecular orbital (LUMO) with the HOMO being almost unchanged, together with the effective broadening on the absorption band.
• Chalcogenophene-Sensitive Charge Carrier Transport Properties in A–D–A′′–D Type NBDO-Based Copolymers for Flexible Field-Effect Transistors
  作者：Keli Shi、Weifeng Zhang、Yankai Zhou、Congyuan Wei、Jianyao Huang、Qiang Wang、Liping Wang、Gui Yu

  DOI：10.1021/acs.macromol.8b01944

  日期：2018.11.13

  The use of chalcogenophenes runs through the whole history of developing high performance pi-conjugated materials toward organic electronics devices. In this work, we report three A-D-A'-D type (3E,7E)-3,7-bis(2-oxo-1H-pyrrolo [2,3-b]pyridin-3(2H)-ylidene)benzo [1,2-b:4,5-b']-difuran-2,6(3H,7H)-dione- (NBDO-) based pi-conjugated copolymers containing different chalcogenophenes, i.e., 4,7 di-(thiophen-2-yl) benzo [c] [1,2,5]thiadiazole (TTT), 4,7-di-(selenophen-2-yl)benzo[c] [1,2,5]thiadiazole (STS), or 4,7-di(selenophen-2-yl)benzo[c][1,2,5]selenadiazole (SSS). The effects of chalcogen atom on their optoelectronic properties were explored by a range of techniques, including thermal, optical, electrochemical, computational, molecular aggregation, and carrier transport properties. Interestingly, both PNBDO-TTT and PNBDO-STS formed highly ordered, crystalline, and lamellar packing thin films with uniform intertwined fibrillar morphologies, whereas PNBDO-SSS only gave random molecular packing thin film with amorphous morphology, despite their similar chemical structures, optical and electrochemical properties. In consequence, PNBDO-TTT and PNBDO-STS-based flexible field-effect transistors on PET substrate exhibited high electron mobilities of 2.41 and 2.68 cm(2) V-1 s(-1), respectively, whereas PNBDO-SSS-based ones only showed a lowered electron mobility of 0.012 cm(2) V-1 s(-1).