5,10-di(n-octyl)-5,10-dihydorindolo[3,2-b]indole | 1422451-95-3

• 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: 5,10-di(n-octyl)-5,10-dihydorindolo[3,2-b]indole
• 英文别名: 5,10-di(n-octyl)-5,10-dihydroindolo[3,2-b]indole；5,10-dioctyl-5,10-dihydroindolo[3,2-b]indole；5,10-Dioctylindolo[3,2-b]indole
• CAS: 1422451-95-3
• 化学式: C₃₀H₄₂N₂
• 分子量: 430.677
• InChiKey: JPEINMPSAVUGFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  9.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5,10-di(n-octyl)-5,10-dihydorindolo[3,2-b]indole 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 3.0h， 以32%的产率得到2,7-dibromo-5,10-dioctyl-5,10-dihydroindolo[3,2-b]indole
  参考文献：
  名称：

  Synthesis and Characterization of Indolo[3,2-b]indole Based Copolymers for Bulk Heterojunction Polymer Solar Cell

  摘要：

  A series of donor-acceptor low band gap polymers (DINIBT-C8, DINIBT-C10 and DINIBT-EH) containing 5,10-dihydroindolo[3,2-b]indole (DINI) as an electron donating unit and benzothiadiazole (BT) as an electron accepting unit with various kinds of alkyl chains (octyl; C8, decyl; C10 and ethyl hexyl; EH) on the donor unit have been designed, synthesized, and characterized for bulk heterojunction polymer solar cell applications. Due to the presence of long alkyl chains on the donor unit, all the polymers showing good solubility in common organic solvents. The frontier orbital energy levels of polymers were calculated using cyclic voltametry analysis. The influence of alkyl chains on the photo-physical properties of polymers were carried out. Among the three polymers, the DINIBT-C8 shows higher absorption coverage and good energy level matching with acceptor PC71BM than that of the other two polymers. Thus, the bulk-heterojunction polymer solar cells (BHJ PSCs) were fabricated using DINIBT-C8:PC71BM as an active layer with the configuration of ITO/PEDOT/ DINIBT-C8:PC71BM/LiF/Al. The DINIBT-C8 shows the maximum PCE of 0.16%.

  DOI：

  10.1080/15421406.2014.932658
• 作为产物：
  描述：

  邻氨基苯甲酸甲酯 在 五氯化磷 、 苄基三乙基氯化铵 、 sodium hydride 、 三氟乙酸 、 sodium hydroxide 、 锌 作用下， 以 四氢呋喃 、 氯仿 、 水 、 二甲基亚砜 为溶剂， 反应 100.0h， 生成 5,10-di(n-octyl)-5,10-dihydorindolo[3,2-b]indole
  参考文献：
  名称：

  带有二氢吡咯并[3,2- b ]吡咯核的杂环丁烯的还原环封闭方法学：范围和局限性

  摘要：

  针对其具有范围和局限性，系统地研究了一种新开发的带有二氢吡咯并[3,2- b ]吡咯核的杂环丁烷的还原性闭环方法。该方法涉及（i）邻氨基苯甲酸酯衍生物的环化以产生八元环状双内酰胺，和（ii）将双内酰胺转化成相应的二亚氨基酰氯，其经历（iii）还原性闭环以安装二氢吡咯并[3,2- b]吡咯核。该方法的第一步由于其底物限制而起关键作用，该底物受到低聚和水解竞争的困扰。所有的双内酰胺都可以成功地转化为相应的二亚氨基氯化物，其中大多数成功地得到了二氢吡咯并[3,2- b]吡咯核。然后使用紫外-可见光谱和循环伏安法系统地研究了取代基和共轭长度的延长对所得杂苯的光物理性质的影响。发现氯化和氟化对杂并苯的光物理性质有很大不同的影响，并且环熔合样式也对杂并苯的带隙有很大的影响。成功地制备一系列带有二氢吡咯并[3，2- b ]吡咯核的杂并苯将为进一步制造有机场效应晶体管器件提供各种各样的候选物。

  DOI：

  10.1021/jo501402n

文献信息

• Synthesis and Characterization of New Dihydroindolo[3,2-b]indole and 5,6-Bis(octyloxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole-Based Polymer for Bulk Heterojunction Polymer Solar Cells
  作者：Kakaraparthi Kranthiraja、Kumarasamy Gunasekar、Myungkwan Song、Yeong-Soon Gal、Jae Wook Lee、Sung-Ho Jin

  DOI：10.5012/bkcs.2014.35.5.1485

  日期：2014.5.20

  We have designed and developed a new ladder type tetrafused $\pi}$-conjugated building block such as dihydroindolo[3,2-b]indole (DINI) and investigated its role as an electron rich unit. The photovoltaic properties of a new semiconducting $\pi}$-conjugated polymer, poly[[5,10-bisoctyl-5,10-dihydroindolo[3,2-b]indole-[5,6- bis(octyloxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole]], represented by PDINI-OBTC8 are described. The new polymer PDINI-OBTC8 was synthesized in donor-acceptor (D-A) fashion, where fused $\pi}$-conjugated tetracyclic DINI, and 5,6-bis(octyloxy)-4,7-di(thiophen-2-yl) benzo[c][1,2,5]thiadiazole (OBTC8) were employed as electron rich (donor) and electron deficient (acceptor) moieties, respectively. The conventional bulk heterojunction (BHJ) device structure ITO/PEDOT:PSS/PDINI-OBTC8:PCB71M/LiF/Al was utilized to fabricate polymer solar cells (PSCs), which comprises the blend of PDINI-OBTC8 and [6,6]-phenyl-$C_71}$-butyric acid methyl ester ($PC_71}BM$) in BHJ network. A BHJ PSC that contain PDINI-OBTC8 delivered power conversion efficiency (PCE) value of 1.68% with 1 vol% of 1,8-diidooctane (DIO) under the illumination of A.M 1.5G 100 $mW/cm^2$.

  我们设计并开发了一种新型梯形四融合 $\pi}$ 共轭结构单元，如二氢吲哚[3,2-b]吲哚（DINI），并研究了其作为富电子单元的作用。本文介绍了以 PDINI-OBTC8 为代表的新型半导体 $\pi}$ 共轭聚合物--聚[[5,10-bisoctyl-5,10-dihydroindolo[3,2-b]indole-[5,6-bis(octyloxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole]]的光伏特性。新型聚合物 PDINI-OBTC8 是以供体-受体（D-A）方式合成的，其中融合的 $\pi}$ 共轭四环 DINI 和 5,6-双（辛氧基）-4,7-二（噻吩-2-基）苯并[c][1,2,5]噻二唑（OBTC8）分别用作富电子（供体）和缺电子（受体）分子。传统的体异质结（BHJ）器件结构 ITO/PEDOT:PSS/PDINI-OBTC8:PCB71M/LiF/Al 被用来制造聚合物太阳能电池（PSC），它由 PDINI-OBTC8 和 [6,6]-phenyl-$C_71}$ 丁酸甲酯（$PC_71}BM$）在 BHJ 网络中的混合物组成。在 A.M 1.5G 100 $mW/cm^2$ 光照下，含有 PDINI-OBTC8 的 BHJ PSC 与 1 vol% 的 1,8-didooctane (DIO) 的功率转换效率 (PCE) 值为 1.68%。
• 5,10-Dihydroindolo[3,2-<i>b</i>]indole-Based Copolymers with Alternating Donor and Acceptor Moieties for Organic Photovoltaics
  作者：Zbyslaw R. Owczarczyk、Wade A. Braunecker、Andres Garcia、Ross Larsen、Alexandre M. Nardes、Nikos Kopidakis、David S. Ginley、Dana C. Olson

  DOI：10.1021/ma301987p

  日期：2013.2.26

  A series of new donor-acceptor pi-conjugated copolymers incorporating 5,10-dihydroindolo[3,2-b]indole (DINI) as an electron donating unit have been designed, synthesized, and explored in bulk heterojunction solar cells with diketopyrrolopyrrole and thienopyrroledione as the electron accepting units. A significant effect of the size and shape of the pendant alkyl substituents attached to the DINI unit on the optical and electronic properties of the copolymers is described. Our study reveals a good correlation between the theoretical calculations performed on the selected materials and the experimental HOMO, LUMO, absorption spectra, and band gap energies of the corresponding copolymers. The band gaps of the conjugated copolymers can be tailored over 0.4 eV by the electron-withdrawing nature of the different acceptor units to provide better overlap with the solar spectrum, and the energy levels can be tuned similar to 0.2 eV depending on the alkyl substituents employed. For the polymers in this study, a nonoptimized power conversion efficiency as high as 3% was observed.