2,7-二溴-4,9-二氢-4,4,9,9-四（4-己基苯基）-s-indaceno[1,2-b：5,6-b']二噻吩 | 1049034-71-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 中文名称: 2,7-二溴-4,9-二氢-4,4,9,9-四（4-己基苯基）-s-indaceno[1,2-b：5,6-b']二噻吩
• 英文名称: 2,7-dibromo-4,4,9,9-tetrakis(4-hexylphenyl)-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophene
• 英文别名: 2,7-dibromo-4,4,9,9-tetrakis-(4-hexylphenyl)-4,9-dihydro-s-indaceno[1,2-b:5,6-b′]dithiophene；2,7-dibromo-4,9-dihydro-4,4,9,9-tetrakis (4-hexylphenyl)-s-indacene[1,2-b:5,6-b']dithiophene；6,15-dibromo-9,9,18,18-tetrakis(4-hexylphenyl)-5,14-dithiapentacyclo[10.6.0.03,10.04,8.013,17]octadeca-1(12),2,4(8),6,10,13(17),15-heptaene
• CAS: 1049034-71-0
• 化学式: C₆₄H₇₂Br₂S₂
• 分子量: 1065.22
• InChiKey: KEJUJAPHYLMYCY-UHFFFAOYSA-N

物化性质

• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  24.8
• 重原子数：
  68
• 可旋转键数：
  24
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，避光干燥密闭保存。

反应信息

• 作为反应物：
  描述：

  2,7-二溴-4,9-二氢-4,4,9,9-四（4-己基苯基）-s-indaceno[1,2-b：5,6-b']二噻吩 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三(邻甲基苯基)磷 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  TWI706955

  摘要：

  公开号：
• 作为产物：
  描述：

  2,5-二溴对苯二甲酸 在 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 硫酸 、 溶剂黄146 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 正庚烷 为溶剂， 反应 10.0h， 生成 2,7-二溴-4,9-二氢-4,4,9,9-四（4-己基苯基）-s-indaceno[1,2-b：5,6-b']二噻吩
  参考文献：
  名称：

  非富勒烯电子受体材料与有机光伏电池

  摘要：

  一种如式(I)所示的非富勒烯电子受体材料与一种其有源层包括前述非富勒烯电子受体材料的有机光伏电池。以本发明的非富勒烯电子受体材料作为电子受体时，能有效提升有机光伏电池的能量转换效率(PCE)。

  公开号：

  CN112390813B

文献信息

• Regioregular pyridal[2,1,3]thiadiazole π-conjugated copolymers for organic semiconductors
  申请人：Bazan Guillermo C.

  公开号：US09293708B2

  公开（公告）日：2016-03-22

  A method of regioselectively preparing a pyridine-containing compound is provided. In particular embodiments, the method includes reacting halogen-functionalized pyridal[2,1,3]thiadiazole with organotin-functionalized cyclopenta[2,1-b:3,4-b′]dithiophene or organotin-functionalized indaceno[1,2-b:5,6-b′]dithiophene. Also provided is a method of preparing a polymer. The method includes regioselectively preparing a monomer that includes a pyridal[2,1,3]thiadiazole unit; and reacting the monomer to produce a polymer that includes a regioregular conjugated backbone section, wherein the section includes a repeat unit containing the pyridal[2,1,3]thiadiazole unit. A polymer that includes a regioregular conjugated backbone section, and electronic devices that include the polymer, are also provided.

  提供了一种区域选择性制备含吡啶化合物的方法。在特定实施例中，该方法包括将卤素功能化的吡啶[2,1,3]噻二唑与有机锡功能化的环戊[2,1-b:3,4-b']二硫噻吩或有机锡功能化的吲哚并[1,2-b:5,6-b']二硫噻吩反应。还提供了一种制备聚合物的方法。该方法包括区域选择性制备包含吡啶[2,1,3]噻二唑单元的单体，并将单体反应以产生包含区域富集的共轭骨架部分的聚合物，其中该部分包含重复单元，其中包含吡啶[2,1,3]噻二唑单元。还提供了包含区域富集的共轭骨架部分的聚合物和包含该聚合物的电子器件。
• Regioregular pyridyl[2,1,3]thiadiazole-co-indacenodithiophene conjugated polymers
  作者：Wen Wen、Lei Ying、Ben B. Y. Hsu、Yuan Zhang、Thuc-Quyen Nguyen、Guillermo C. Bazan

  DOI：10.1039/c3cc43229g

  日期：——

  Regioregular conjugated polymers containing alternating pyridyl[2,1,3]thiadiazole (PT) and indacenodithiophene (IDT) structural units were synthesized. In these copolymers, the pyridyl nitrogen atoms on PT are precisely arranged along the backbone so that each one has an adjacent proximal and an adjacent distal counterpart across the two IDT flanking units. We find that despite the absence of obvious differences in orbital energy levels and optical bandgap, the regioregular materials exhibit larger charge carrier mobilities, as determined by using field effect transistor devices, and can yield higher solar cell power conversion efficiencies when mixed with fullerenes in bulk heterojunction active layers.

  我们合成了含有吡啶并[2,1,3]噻二唑（PT）和茚并噻吩（IDT）交替结构单元的正交共轭聚合物。在这些共聚物中，PT 上的吡啶基氮原子沿着骨架精确排列，因此每个氮原子在两个 IDT 侧翼单元上都有一个相邻的近端和一个相邻的远端对应物。我们发现，尽管在轨道能级和光带隙方面没有明显的差异，但通过使用场效应晶体管器件测定，这些团状材料表现出更大的电荷载流子迁移率，与富勒烯混合制成体异质结活性层时，可产生更高的太阳能电池功率转换效率。
• Preparation and Characterization of a Novel Organic Semiconductor Indacenedithiophene Derivative and the Corresponding Langmuir-Blodgett Thin Films
  作者：Violeta Alvarez-Venicio、Rafael O. Arcos-Ramos、José Alfonso Hernández-Rojas、Jaime Octavio Guerra-Pulido、Vladimir A. Basiuk、Margarita Rivera、María del Pilar Carreón-Castro

  DOI：10.1166/jnn.2019.17129

  日期：2019.11.1

  The synthesis of a novel indacenedithiophene derivative (IDT-DPA) is described, which exhibits semiconducting behavior. Its properties were measured by means of UV-visible and fluorescence spectroscopies using toluene as solvent. An extinction molar coefficient of 2.05×10⁴ M⁻¹ cm⁻¹ and a Stokes shift of 50 nm were obtained. A theoretical study was performed using the density functional theory, from which HOMO–LUMO band gap of 1.711 eV was calculated. IDT-DPA was deposited on the water-air interface to form Langmuir monolayers. π-A curves and hysteresis were measured showing reversibility behavior. The monolayers were transferred to glass substrates as Langmuir-Blodgett thin films. Their morphological properties were characterized by using scanning electron and atomic force microscopy, which showed that the films tend to form clusters with a homogeneous distribution. Absorption and emission spectra of the films were measured, from which the optical band gap and Stocks shift were derived. Based on the electronic properties and light emission spectra of IDT-DPA, this compound can be proposed for the applications in organic lightemitting diodes and other organic semiconductor devices.

  本文介绍了一种新型的吲哚并二噻吩衍生物(IDT-DPA)的合成方法，其具有半导体行为。使用甲苯作为溶剂，通过紫外-可见光谱和荧光光谱测量了其性质。得到了一个消光系数为2.05×10⁴ M⁻¹ cm⁻¹和50 nm的斯托克斯位移。使用密度泛函理论进行了理论研究，计算出了HOMO-LUMO能隙为1.711 eV。将IDT-DPA沉积在水-空气界面上形成Langmuir单分子层，测量了π-A曲线和滞后现象，显示出可逆行为。将单分子层转移到玻璃基底上形成Langmuir-Blodgett薄膜。使用扫描电子和原子力显微镜表征了其形态学特性，结果显示薄膜倾向于形成具有均匀分布的簇。测量了薄膜的吸收和发射光谱，从中得出了光学带隙和斯托克斯位移。基于IDT-DPA的电子性质和光发射光谱，可以将该化合物推荐用于有机发光二极管和其他有机半导体器件的应用。
• REGIOREGULAR PYRIDAL[2,1,3]THIADIAZOLE PI-CONJUGATED COPOLYMERS FOR ORGANIC SEMICONDUCTORS
  申请人：BAZAN Guillermo C.

  公开号：US20120322966A1

  公开（公告）日：2012-12-20

  A method of regioselectively preparing a pyridine-containing compound is provided. In particular embodiments, the method includes reacting halogen-functionalized pyridal[2,1,3]thiadiazole with organotin-functionalized cyclopenta[2,1-b:3,4-b′]dithiophene or organotin-functionalized indaceno[1,2-b:5,6-b′]dithiophene. Also provided is a method of preparing a polymer. The method includes regioselectively preparing a monomer that includes a pyridal[2,1,3]thiadiazole unit; and reacting the monomer to produce a polymer that includes a regioregular conjugated backbone section, wherein the section includes a repeat unit containing the pyridal[2,1,3]thiadiazole unit. A polymer that includes a regioregular conjugated backbone section, and electronic devices that include the polymer, are also provided.

  提供了一种区域选择性制备含吡啶化合物的方法。特别地，该方法包括将卤代功能化的吡啶并[2,1,3]噻二唑与有机锡功能化的环戊[2,1-b:3,4-b′]二硫苯或有机锡功能化的吲哚并[1,2-b:5,6-b′]二硫苯反应。还提供了一种制备聚合物的方法。该方法包括区域选择性地制备包含吡啶并[2,1,3]噻二唑单元的单体；并反应该单体以产生包含区域规则的共轭骨架部分的聚合物，其中该部分包含含有吡啶并[2,1,3]噻二唑单元的重复单元。还提供了一种包含区域规则的共轭骨架部分的聚合物和包含该聚合物的电子器件。
• Indacenodithiophene core-based small molecules with tunable side chains for solution-processed bulk heterojunction solar cells
  作者：Xin Liu、QingDuan Li、Yunchuan Li、Xiong Gong、Shi-Jian Su、Yong Cao

  DOI：10.1039/c3ta14659f

  日期：——

  different side chains of bulky 4-hexylphenyl and flexible n-dodecyl with the same number of carbon atom, namely SM1 and SM2, respectively, were designed and synthesized as the donor materials in organic solar cells (OSCs). The impacts of the different side chains combined with the IDT core on the optical absorption, electrochemical property, hole mobility, film morphology, and solar cell performance

  两个indacenodithiophene（IDT）基于核的小分子体积大的4-己基苯基和柔性的不同侧链Ñ具有相同数目的碳原子，即十二烷基SM1和SM2，分别设计并作为供体材料的有机太阳能合成单元（OSC）。深入研究了不同侧链结合IDT核对光吸收，电化学性能，空穴迁移率，薄膜形态和太阳能电池性能的影响。两种化合物在450-700 nm的波长范围内具有较宽的吸收率，相对较低的HOMO能级为-5.46和-5.52 eV。基于SM2作为供体材料的OSC的功率转换效率（PCE）和PC61 BM作为受体材料（1：2，w / w）为2.33％。相反，对于基于SM1作为施主和PC 71 BM作为受主（1：2，w / w）的装置，无需任何处理，例如热退火或利用溶剂添加剂，即可获得4.72％的PCE。