(E)-6,6'-dibromo-1,1'-bis(2-hexyldecyl)-[3,3'-biindolinylidene]-2,2'-dione | 1309375-12-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E)-6,6'-dibromo-1,1'-bis(2-hexyldecyl)-[3,3'-biindolinylidene]-2,2'-dione
• 英文别名: 6,6'-Dibromo-1,1'-bis(2-hexyldecyl)isoindigo；(3E)-6-bromo-3-[6-bromo-1-(2-hexyldecyl)-2-oxoindol-3-ylidene]-1-(2-hexyldecyl)indol-2-one
• CAS: 1309375-12-9
• 化学式: C₄₈H₇₂Br₂N₂O₂
• 分子量: 868.92
• InChiKey: ASEPOMMRUTXNGO-XVIFHXHVSA-N

物化性质

• 沸点：
  783.3±60.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  18.3
• 重原子数：
  54
• 可旋转键数：
  28
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-6,6'-dibromo-1,1'-bis(2-hexyldecyl)-[3,3'-biindolinylidene]-2,2'-dione 、 1-乙炔基芘 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 24.0h， 以68%的产率得到(3E)-1-(2-hexyldecyl)-3-[1-(2-hexyldecyl)-2-oxo-6-(2-pyren-1-ylethynyl)indol-3-ylidene]-6-(2-pyren-1-ylethynyl)indol-2-one
  参考文献：
  名称：

  Improved photovoltaic performance of D–A–D-type small molecules with isoindigo and pyrene units by inserting different π-conjugated bridge

  摘要：

  Two novel D-pi-A-pi-D-type small molecules (SMs) of IID(Ac-Py)(2) and IID(Th-Py)(2) were synthesized and characterized, in which isoindigo (IID), acetylene (Ac) or thiophene (Th), and pyrene (Py) were used as the acceptor (A) core, extended pi-bridges, and donor (D) terminal units, respectively. Significantly improved photophysical and photovoltaic performances were observed for both SMs containing extended pi-bridge in comparison with those for their parent D-A-D type molecule of IID(Py)(2). Compared to IID(Ac-Py)(2), IID(Th-Py)(2) shows a better photovoltaic performance due to broader absorption, deeper HOMO levels (-5.44 eV) and better morphology of the devices. A maximum power conversion efficiency (PCE) of 1.88% with a short-circuit current density Usc) of 6.90 mA cm(-2) was obtained in the IID(Th-Py)(2)/PC71BM-based solar cells, which is 235 times the value of IID(Ac-Py)(2)-based cells. Particularly, the IID(Th-Py)(2)/PC61BM-based device exhibited a Vac value up to 1.01 V, which is 0.27 V and 0.12 V higher than IID(Py)(2)/and IlD(Ac-Py)(2)/PC61BM-based devices, respectively. To our best knowledge, the Vac of 1.01 V is among the highest values in literature for solution processed SMs OSCs without any post processing. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2016.06.016

文献信息

• KETOPYRROLES AS ORGANIC SEMICONDUCTORS
  申请人：Flores Jean-Charles

  公开号：US20100297405A1

  公开（公告）日：2010-11-25

  Monomeric or polymeric compounds comprising at least one moiety of the formula (Ia) wherein X is CR, where R is H or a substituent as defined in claim 1, or is another ketopyrrole moiety e.g. of the formula (1 b ) or (1 c ) with this moiety and all other symbols are as defined in claim 1, show good solubility in organic solvents and excellent film-forming properties. In addition, high efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the polymers according to the invention are used in semiconductor devices or organic photovoltaic (PV) devices (solar cells).

  单体或聚合物化合物至少包含式(Ia)中的一个基团，其中X为CR，其中R为H或按照权利要求1中定义的取代基，或为另一个酮吡咯基团，例如式(1b)或(1c)，其中此基团和所有其他符号如权利要求1所定义，显示出在有机溶剂中良好的溶解性和优异的成膜性能。此外，当根据本发明的聚合物用于半导体器件或有机光伏（PV）器件（太阳能电池）时，可以观察到高效的能量转换、优异的场效应迁移率、良好的开关电流比和/或优异的稳定性。
• Synthesis and characterization of benzodithiophene–isoindigo polymers for solar cells
  作者：Zaifei Ma、Ergang Wang、Markus E. Jarvid、Patrik Henriksson、Olle Inganäs、Fengling Zhang、Mats R. Andersson

  DOI：10.1039/c1jm14940g

  日期：——

  Three new alternating polymers with the electron-deficient isoindigo group as the acceptor unit and benzo[1,2-b:4,5-b′]dithiophene (BDT) or BDT flanked by thiophenes (or octylthiophenes) as the donor unit were designed and synthesized. All the polymers have good thermal stability, solubility and broad absorption spectra. Their photophysical, electrochemical and photovoltaic (PV) properties were investigated. To understand their different PV performance in the resulting polymer solar cells (PSCs), the morphology of their blends with fullerene derivatives was investigated by atomic force microscopy, and the molecular geometries as well as the molecular frontier orbitals were simulated by density functional theory calculations (Gaussian 09). The polymer PBDT-TIT, with BDT flanked by thiophenes as the donor unit and isoindigo as the acceptor unit, exhibits quite planar backbones and its blend with fullerene derivatives shows optimal morphology. As a result, the PSCs based on PBDT-TIT with a conventional device configuration of ITO/PEDOT:PSS/PBDT-TIT:PC61BM/LiF/Al showed a power conversion efficiency of 4.22%, with a short-circuit current density of 7.87 mA cm−2, an open-circuit voltage of 0.79 V and a fill factor of 0.68 under the AM 1.5G illumination with an intensity of 100 mW cm−2 from a solar simulator.

  三种新型交替聚合物以缺电子异靛基作为受体单元，苯并[1,2-b:4,5-b-]二噻吩（BDT）或侧翼为噻吩（或辛基噻吩）的BDT作为供体单元设计并合成。所有聚合物都具有良好的热稳定性、溶解性和宽的吸收光谱。研究了它们的光物理、电化学和光伏（PV）特性。为了了解它们在所得聚合物太阳能电池（PSC）中的不同光伏性能，通过原子力显微镜研究了它们与富勒烯衍生物的共混物的形态，并通过密度泛函理论计算模拟了分子几何形状以及分子前沿轨道（高斯 09)。聚合物PBDT-TIT以BDT为侧翼的噻吩作为供体单元，异靛蓝作为受体单元，表现出相当平面的主链，并且其与富勒烯衍生物的共混物显示出最佳的形态。结果，基于PBDT-TIT且传统器件配置为ITO/PEDOT:PSS/PBDT-TIT:PC61BM/LiF/Al的PSC的功率转换效率为4.22%，短路电流密度为7.87 mA cm-2，在来自太阳模拟器的 AM 1.5G 照明、强度为 100 mW cm-2 下，开路电压为 0.79 V，填充因子为 0.68。
• PREPARATION OF HIGH MOLECULAR WEIGHT POLYMERS BY DIRECT ARYLATION AND HETEROARYLATION
  申请人：UNIVERSITE LAVAL

  公开号：US20140371409A1

  公开（公告）日：2014-12-18

  A method for preparing polymers by direct heteroarylation or arylation polycondensation is described herein. The method includes preparing a reaction mixture including at least a monomer to be polymerized, a catalyst and a ligand; heating the reaction mixture, and, optionally, end-capping the reaction mixture.

  本文描述了一种通过直接杂环化或芳基化聚合制备聚合物的方法。该方法包括制备反应混合物，其中至少包括一个要聚合的单体、一个催化剂和一个配体；加热反应混合物，以及可选地对反应混合物进行端基化处理。
• A direct arylation approach towards efficient small molecule organic solar cells
  作者：Julija Kudrjasova、Jurgen Kesters、Pieter Verstappen、Jeroen Brebels、Tim Vangerven、Ilaria Cardinaletti、Jeroen Drijkoningen、Huguette Penxten、Jean Manca、Laurence Lutsen、Dirk Vanderzande、Wouter Maes

  DOI：10.1039/c5ta09023g

  日期：——

  Direct arylation affords organic semiconductors enabling high solar cell efficiency upon careful removal of the ‘miss-coupled’ side products.

  直接芳基化反应可制备有机半导体，通过精心去除“失配”的副产物，可实现高效率太阳能电池。
• Phenanthrodithiophene–Isoindigo Copolymers: Effect of Side Chains on Their Molecular Order and Solar Cell Performance
  作者：Shuhei Nishinaga、Hiroki Mori、Yasushi Nishihara

  DOI：10.1021/acs.macromol.5b00622

  日期：2015.5.12

  The synthesis, characterization, and solar cell application of newly developed semiconducting polymers containing phenanthro[1,2-b:8,7-b′]dithiophene (PDT) combined with a bis(thienyl)isoindigo (IID) unit are described. The polymers with longer alkyl chains are sufficiently soluble to be compatible with the processes required to manufacture solar cells. In conventional solar cell devices, polymers with

  新开发的含菲[[1,2- b：8,7- b]的半导体聚合物的合成，表征和太阳能电池应用描述了与双（噻吩基）异靛蓝（IID）单元组合的']二噻吩（PDT）。具有较长烷基链的聚合物具有足够的可溶性，以与制造太阳能电池所需的工艺相容。在传统的太阳能电池设备中，与具有直链和支链烷基链的聚合物相比，具有所有支链烷基链的聚合物在π堆叠方向上倾向于形成比例更高的有序面对微晶，这显着提高了填充系数（ FF），从而提高了电源转换效率（PCE）。就优化烷基链长度而言，在聚合物主链上安装更长的烷基侧链会导致低分子量聚合物，这可能会促进大的相分离。结果，聚合物12OD和BOBO，具有较短烷基的，性能更好，BOBO聚合物基太阳能电池（PSC）的最佳PCE值高达3.83％。在倒置的PSC中，具有所有支链烷基链的聚合物具有比具有直链和支链烷基链的聚合物更高的面对比率。由于改进了J sc，BOBO / PC 71 BM的反向PSC表现最佳，PCE高达5