5,10-bis(n-octly)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,10-dihydroindolo[3,2-b]indole | 1422452-03-6

• 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-bis(n-octly)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,10-dihydroindolo[3,2-b]indole
• 英文别名: 5,10-bis(n-octyl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,10-dihydroindolo[3,2-b]indole；5,10-Dioctyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolo[3,2-b]indole；5,10-dioctyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolo[3,2-b]indole
• CAS: 1422452-03-6
• 化学式: C₄₂H₆₄B₂N₂O₄
• 分子量: 682.603
• InChiKey: UHOXZTVMYBUKPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.07
• 重原子数：
  50
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,2-双(2-硝基苯基)乙烷-1,2-二酮 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 tin(II) chloride dihdyrate 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 9.0h， 生成 5,10-bis(n-octly)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,10-dihydroindolo[3,2-b]indole
  参考文献：
  名称：

  新型二氢吲哚[3,2-b]吲哚和5,6-双(辛氧基)-4,7-二(噻吩-2-基)苯并[c][1,2,5]噻二唑基的合成与表征体异质结聚合物太阳能电池用聚合物

  摘要：

  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%。

  DOI：

  10.5012/bkcs.2014.35.5.1485

文献信息

• 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.
• 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%。