4-(2-bromo-9,9'-spirobiuorene-7-yl)-N,N-diphenylaniline | 1245645-82-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(2-bromo-9,9'-spirobiuorene-7-yl)-N,N-diphenylaniline
• 英文别名: 2-bromo-7-(4-(diphenylamino)phenyl)-9,9-spirobifluorene；4-(7'-bromo-9,9'-spirobi[fluorene]-2'-yl)-N,N-diphenylaniline
• CAS: 1245645-82-2
• 化学式: C₄₃H₂₈BrN
• 分子量: 638.606
• InChiKey: UXOIUFHXUGZQAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  45
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.02
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5-(1,3-二氧杂烷-2-基)-4-己基噻吩-2-基)三丁基锡 、 4-(2-bromo-9,9'-spirobiuorene-7-yl)-N,N-diphenylaniline 在 四(三苯基膦)钯 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 48.5h， 以33%的产率得到5-(2-(4-(diphenylamino)phenyl)-9,9-spirobifluoren-7-yl)-3-hexylthiophene-2-carbaldehyde
  参考文献：
  名称：

  Efficient triphenylamine-based dyes featuring dual-role carbazole, fluorene and spirobifluorene moieties

  摘要：

  Three triphenylamine-based organic dyes SD6, SD7, and SD8 containing the bulky dual-role moieties (fluorene, carbazole, and spirobifluorene) in the molecular frameworks were synthesized, characterized and applied in dye-sensitized solar cells (DSSCs). The effects of dual-role moieties of organic dyes on their photophysical, electrochemical, and photovoltaic properties have been investigated in detail. These dyes exhibit strong charge transfer absorption bands in the visible region. Their redox potential levels were estimated by cyclic voltammetry and found to suit well to the charge flow in DSSCs. Inserting the dual-role moieties as the secondary donor between the triphenylamine and thiophene units increased the electron density of the donor groups, therefore reduced the HOMO-LUMO band gaps. The combination of ultraviolet-visible (UV-vis) region broad absorption bands with fairly high extinction coefficients and appropriate redox properties observed in these triphenylamine-based dyes make them promising dyes for DSSCs. For a typical solar cell device based on dye SD6, the maximal monochromatic incident photon-to-current conversion efficiency (IPCE) can reach to similar to 73%, with a short-circuit photocurrent density (J(sc)) of 14.25 mA/cm(2), an open-circuit photovoltage (V-oc) of 0.70 V, and a fill factor (FF) of 0.705, which corresponds to a power conversion efficiency (PCE) of 7.03%. (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.orgel.2010.10.016
• 作为产物：
  描述：

  4-(二苯基氨基)苯硼酸频那醇酯 、 2,7-二溴-9,9'-螺二芴 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 48.0h， 以69%的产率得到4-(2-bromo-9,9'-spirobiuorene-7-yl)-N,N-diphenylaniline
  参考文献：
  名称：

  Efficient triphenylamine-based dyes featuring dual-role carbazole, fluorene and spirobifluorene moieties

  摘要：

  Three triphenylamine-based organic dyes SD6, SD7, and SD8 containing the bulky dual-role moieties (fluorene, carbazole, and spirobifluorene) in the molecular frameworks were synthesized, characterized and applied in dye-sensitized solar cells (DSSCs). The effects of dual-role moieties of organic dyes on their photophysical, electrochemical, and photovoltaic properties have been investigated in detail. These dyes exhibit strong charge transfer absorption bands in the visible region. Their redox potential levels were estimated by cyclic voltammetry and found to suit well to the charge flow in DSSCs. Inserting the dual-role moieties as the secondary donor between the triphenylamine and thiophene units increased the electron density of the donor groups, therefore reduced the HOMO-LUMO band gaps. The combination of ultraviolet-visible (UV-vis) region broad absorption bands with fairly high extinction coefficients and appropriate redox properties observed in these triphenylamine-based dyes make them promising dyes for DSSCs. For a typical solar cell device based on dye SD6, the maximal monochromatic incident photon-to-current conversion efficiency (IPCE) can reach to similar to 73%, with a short-circuit photocurrent density (J(sc)) of 14.25 mA/cm(2), an open-circuit photovoltage (V-oc) of 0.70 V, and a fill factor (FF) of 0.705, which corresponds to a power conversion efficiency (PCE) of 7.03%. (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.orgel.2010.10.016

文献信息

• A new class of three-dimensional, p-type, spirobifluorene-modified perylene diimide derivatives for small molecular-based bulk heterojunction organic photovoltaic devices
  作者：Chin-Yiu Chan、Yi-Chun Wong、Hok-Lai Wong、Mei-Yee Chan、Vivian Wing-Wah Yam

  DOI：10.1039/c4tc01001a

  日期：——

  A new class of non-planar and three-dimensional spirobifluorene-modified perylene diimide compounds has been successfully designed and synthesized. The functionalization of the perylene diimide core with different spirobifluorene moieties can alter the molecular geometry as well as extend the spectral coverage into the red region. In addition, these compounds can be utilized as donor materials in combination with fullerene to form bulk heterojunctions, and particularly efficient organic photovoltaic (OPV) devices demonstrating high open-circuit voltages of 0.97 V and a power conversion efficiencies of up to 4% have been prepared. These values are the highest among the cells utilizing p-type perylene diimide as photoactive material in OPV devices. This work opens up a new avenue for the design and synthesis of a new class of p-type perylene diimide compounds that are promising candidates as donor materials in the fabrication of OPV devices.

  一种新型的非平面和三维螺双氟苊修饰的苝二酰亚胺化合物已经成功设计和合成。用不同的螺双氟苊基团对苝二酰亚胺核心进行功能化可以改变分子的几何形状，并将光谱覆盖范围扩展到红色区域。此外，这些化合物可以与富勒烯结合，作为供体材料形成大块异质结，并成功制备出特别高效的有机光伏(OPV)器件，展现出0.97 V的高开路电压和高达4%的光电转换效率。这个值是在以p型苝二酰亚胺作为光活性材料的OPV器件中所达到的最高水平。这项工作为设计和合成新型p型苝二酰亚胺化合物开辟了一条新的途径，这些化合物作为OPV器件制造中的供体材料具有良好的前景。