4,7-di-2-furyl-2,1,3-benzothiadiazole | 287976-98-1

• 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-2-furyl-2,1,3-benzothiadiazole
• 英文别名: 4,7-Di(furan-2-yl)benzo[c][1,2,5]thiadiazole；4,7-bis(furan-2-yl)-2,1,3-benzothiadiazole
• CAS: 287976-98-1
• 化学式: C₁₄H₈N₂O₂S
• 分子量: 268.296
• InChiKey: BJEBVQSFQBACNV-UHFFFAOYSA-N

物化性质

• 沸点：
  434.6±35.0 °C(Predicted)
• 密度：
  1.371±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  80.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,7-di-2-furyl-2,1,3-benzothiadiazole 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  噻吩/呋喃取代对芳基噻二唑基有机半导体有机场效应晶体管性能的影响

  摘要：

  对于有机场效应晶体管（OFET）应用，研究了四种供体-受体（D-A）型有机半导体，它们由5-己基噻吩与噻吩/呋喃侧苯并噻二唑/萘噻二唑组成。尽管呋喃是噻吩的类似物，但由于其与噻吩的性质不同以及光化学氧化的不稳定性，它在有机电子领域的关注较少。但是，这项研究确定呋喃可以显示与其类似物相当的电荷传输性质。研究了带有苯并基和不同杂原子侧翼基团的电子接受噻二唑核的扩展，表明OFET的性能取决于分子轨道，几何形状和堆积。底栅底接触装置的配置用于研究所有分子的OFET传输性质。我们成功地证明了呋喃单元是一种有希望的流动性构建基块（μ最大）的0.0122厘米2 V -1小号-1用于使用设备呋喃基取代的苯并噻二唑作为沟道层。

  DOI：

  10.1039/d0tc04982d
• 作为产物：
  描述：

  2,1,3-苯并噻二唑 在 四(三苯基膦)钯 、 氢溴酸 、 溴 作用下， 以 水 、 甲苯 为溶剂， 反应 30.0h， 生成 4,7-di-2-furyl-2,1,3-benzothiadiazole
  参考文献：
  名称：

  胆甾醇液晶中通过不对称电化学聚合制备的杂芳族共轭聚合物薄膜的光学活性：手性诱导的结构功能

  摘要：

  我们在左旋螺旋胆甾型液晶（CLC）介质中电化学聚合了各种非手性杂芳族单体。圆二色性（CD）光谱显示，大多数所得共轭聚合物薄膜在其吸收最大值附近均表现出第一负棉花效应和第二正棉花效应。这表明共轭主链的左旋螺旋聚集，这与CLC的左旋螺旋顺序一致。该结果表明，在电沉积期间，左旋螺旋CLC环境引起聚合物的左旋螺旋聚集。然而，聚合物的CD强度取决于母体单体的结构。

  DOI：

  10.1021/ma400302j

文献信息

• HIGHLY-FLUORESCENT AND PHOTO-STABLE CHROMOPHORES FOR ENHANCED SOLAR HARVESTING EFFICIENCY
  申请人：NITTO DENKO CORPORATION

  公开号：US20130074927A1

  公开（公告）日：2013-03-28

  The invention provides highly fluorescent materials comprising a single (n=0) or a series (n=1, 2, etc.) of benzo heterocyclic systems. The photo-stable highly luminescent chromophores are useful in various applications, including in wavelength conversion films. Wavelength conversion films have the potential to significantly enhance the solar harvesting efficiency of photovoltaic or solar cell devices.

  这项发明提供了包括单个（n=0）或一系列（n=1、2等）苯并杂环系统的高荧光材料。这种光稳定的高发光色团在各种应用中很有用，包括波长转换膜。波长转换膜有潜力显著提高光伏或太阳能电池器件的太阳能收集效率。
• Correlation between structure and photovoltaic performance of a series of furan bridged donor–acceptor conjugated polymers
  作者：Jianyu Yuan、Zhichun Zhai、Jing Li、Jialing Lu、Xiaodong Huang、Zhongjie Xu、Wanli Ma

  DOI：10.1039/c3ta12210g

  日期：——

  A series of donor–acceptor (D–A) polymers based on furan-bridged benzodithiophene and different acceptor blocks were designed and synthesized. By incorporating various acceptors with differing electron-withdrawing abilities into the same polymer backbone, we were seeking to reveal the correlation between molecular structures and the corresponding film morphology as well as photovoltaic performance

  设计并合成了一系列基于呋喃桥联苯并二噻吩和不同受体嵌段的供体-受体（DA）聚合物。通过将具有不同吸电子能力的各种受体结合到同一聚合物主链中，我们试图揭示分子结构与相应的膜形态以及光伏性能之间的相关性。实验结果和理论计算表明，受体单元的选择对聚合物的能级和主链共面性有重大影响，导致分子间的堆积不同。通过使用原子力显微镜和透射电子显微镜，我们还观察到受体上烷基链的大小和拓扑可以调节聚合物的溶解度并导致不同的薄膜形态。
• PROCESS FOR THE PREPARATION OF BENZOHETERO [1,3] - DIAZOLE COMPOUNDS DISUBSTITUTED WITH HETEOARYL GROUPS
  申请人：Schimperna Giuliana

  公开号：US20140221663A1

  公开（公告）日：2014-08-07

  Process for the preparation of a benzohetero[1,3]diazole compound disubstituted with heteroaryl groups which comprises reacting at least one benzohetero[1,3]diazole compound disubstituted with at least one heteroaryl compound. Said benzohetero[1,3]diazole compound disubstituted with heteroaryl groups can be advantageously used in the construction of luminescent solar concentrators (LSC). Furthermore, said benzohetero[1,3]diazole compound disubstituted with heteroaryl groups can be advantageously used in the construction of photovoltaic devices such as, for example, photovoltaic cells, photovoltaic modules, solar cells, solar modules, on both a rigid and flexible support. Said benzohetero[1,3]diazole compound disubstituted with heteroaryl groups can also be advantageously used as a precursor of monomeric units in the preparation of semiconductor polymers.

  制备二取代杂芳并[1,3]二唑化合物的过程包括反应至少一种二取代杂芳并[1,3]二唑化合物和至少一种杂芳基化合物。具有杂芳基的二取代杂芳并[1,3]二唑化合物可优势地用于构建发光太阳能浓缩器（LSC）。此外，具有杂芳基的二取代杂芳并[1,3]二唑化合物可优势地用于构建光伏器件，例如光伏电池、光伏模块、太阳能电池、太阳能模块，均可采用刚性和柔性支撑。具有杂芳基的二取代杂芳并[1,3]二唑化合物还可优势地用作半导体聚合物制备中单体单位的前体。
• [EN] PROCESS FOR THE PREPARATION OF BENZOHETERO [ 1, 3 ] - DIAZOLE COMPOUNDS DISUBSTITUTED WITH HETEOARYL GROUPS<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE COMPOSÉS BENZOHÉTÉRO[1,3]-DIAZOLE DISUBSTITUÉ PAR DES GROUPES HÉTÉROARYLE
  申请人：ENI SPA

  公开号：WO2013021315A1

  公开（公告）日：2013-02-14

  Process for the preparation of a benzohetero [ 1, 3 ] diazole compound disubstituted with heteroaryl groups which comprises reacting at least one benzohetero [ 1, 3 ] diazole compound disubstituted with at least one heteroaryl compound. Said benzohetero [ 1, 3 ] diazole compound disubstituted with heteroaryl groups can be advantageously used in the construction of luminescent solar concentrators (LSC). Furthermore, said benzohetero [ 1, 3 ] diazole compound disubstituted with heteroaryl groups can be advantageously used in the construction of photovoltaic devices such as, for example, photovoltaic cells, photovoltaic modules, solar cells, solar modules, on both a rigid and flexible support. Said benzohetero [ 1, 3 ] diazole compound disubstituted with heteroaryl groups can also be advantageously used as a precursor of monomeric units in the preparation of semiconductor polymers.

  制备一种双取代杂芳基苯并杂二唑化合物的过程，包括将至少一种双取代杂芳基苯并杂二唑化合物与至少一种杂芳基化合物反应。该含有杂芳基苯并杂二唑化合物可以优势地用于构建发光太阳能浓缩器（LSC）。此外，该含有杂芳基苯并杂二唑化合物可以优势地用于构建刚性和柔性支撑下的光伏器件，例如光伏电池、光伏模块、太阳能电池和太阳能模块。该含有杂芳基苯并杂二唑化合物也可以优势地用作半导体聚合物制备中单体单元的前体。
• C–H Arylation of Unsubstituted Furan and Thiophene with Acceptor Bromides: Access to Donor–Acceptor–Donor-Type Building Blocks for Organic Electronics
  作者：Rukiya Matsidik、Johannes Martin、Simon Schmidt、Johannes Obermayer、Florian Lombeck、Fritz Nübling、Hartmut Komber、Daniele Fazzi、Michael Sommer

  DOI：10.1021/jo502432e

  日期：2015.1.16

  Pd-catalyzed direct arylation (DA) reaction conditions have been established for unsubstituted furan (Fu) and thiophene (Th) with three popular acceptor building blocks to be used in materials for organic electronics, namely 4,7-dibromo-2,1,3-benzothiadiazole (BTBr2), N,N'-dialkylated 2,6-dibromonaphthalene-1,4,5,8-bis(dicarboximide) (NDIBr2), and 1,4-dibromotetrafluorobenzene (F4Br2). Reactions with BTBr2, F4Br2, and NDIBr2 require different solvents to obtain high yields. The use of dimethylacetamide (DMAc) is essential for the successful coupling of BTBr2 and F4Br2, but detrimental for NDIBr2, as the electron-deficient NDI core is prone to nucleophilic core substitution in DMAc as solvent but not in toluene. NDIFu(2) is much more planar compared to NDITh2, resulting in an enhanced charge-transfer character, which makes it an interesting building block for conjugated systems designed for organic electronics. This study highlights direct arylation as a simple and inexpensive method to construct a series of important donor-acceptor-donor building blocks to be further used for the preparation of a variety of conjugated materials.