2,7-dibromo-5,5,10,10-tetraphenyl-5,10-dihydroindeno[2,1-a]indene | 1591698-52-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,7-dibromo-5,5,10,10-tetraphenyl-5,10-dihydroindeno[2,1-a]indene
• 英文别名: 2,7-Dibromo-5,5,10,10-tetraphenylindeno[2,1-a]indene
• CAS: 1591698-52-0
• 化学式: C₄₀H₂₆Br₂
• 分子量: 666.454
• InChiKey: HFZYLALWMVAHPG-UHFFFAOYSA-N

物化性质

• 熔点：
  393 °C(Solv: toluene (108-88-3))
• 沸点：
  617.0±55.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  42
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,7-dibromo-5,5,10,10-tetraphenyl-5,10-dihydroindeno[2,1-a]indene 在 吡啶 、 四(三苯基膦)钯 、 potassium acetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 、 甲苯 为溶剂， 反应 57.5h， 生成 2-((5-(7-(4-(diphenylamino)phenyl)-5,5,10,10-tetraphenyl-5,10-dihydroindeno[2,1-a]inden-2-yl)furan-2-yl)-methylene)malononitrile
  参考文献：
  名称：

  Novel dipolar 5,5,10,10-tetraphenyl-5,10-dihydroindeno[2,1-a]-indene derivatives for SM-OPV: A combined theoretical and experimental study

  摘要：

  In order to investigate the photo-physical, electrochemical, and optoelectronic properties of dipolar 5,5,10,10-tetraphenyl-5,10-dihydroindeno[2,1-a]-indene (TDI) derivatives, a facile synthesis has been developed to integrate arylamine (electron donor fragment, D) and aryl-2-methylenemalononitrile (electron acceptor fragment, A) into the TDI bridge. According to calculation results using the DFT/B3LYP/6-31G(d) method, the HOMO and LUMO energies of TDI derivatives are relevant to the extent of corresponding electron donating and accepting abilities, and influence the open-circuit voltage (V-oc) and driving force (Delta E) in organic photovoltaics (OPV). The projected density of state (pDOS) analysis shows that the electron density distribution from the D fragment to TDI bridge in the HOMO is attributing to the electron-donating ability, whereas the electrons are mainly localized on A fragment in the LUMO. Calculations of the reorganization energy by the DFT/B3LYP/6-31G(d) method suggest these D-TDI-A derivatives are hole-transporting type materials. On the other hand, the calculated absorption spectra for these molecules in CH2Cl2 are simulated by using the TD-DFT/BH and HLYP/6-31G(d) method within the Polarizable Continuum Model (PCM) and provide the maximum absorption wavelength (lambda(max)), which can be assigned to the HOMO to LUMO transition. HOMO is found to be the pi orbital which is delocalized between the D fragment and the pi-linker and LUMO is the pi* orbital which is concentrated on the A fragment. The optical properties of D-TDI-A derivatives can be influenced by the D fragment and pi-conjugated length. Calculated results of D-TDI-A derivatives also exhibited a large light harvesting efficiency related to the maximum absorption wavelength (RLHE)) and, according to these results, the D-TDI-A derivatives containing the A(b) and A(d) fragments would be useful electron donor materials for further development of new small molecular organic photovoltaic solar cell (SM-OPV) devices. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2014.10.031
• 作为产物：
  描述：

  1-phenylethynyl-2-diphenylhydroxymethylbenzene 在 aluminum oxide 、 萘 、 三氟化硼乙醚 、 lithium 、 copper(I) bromide 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 2,7-dibromo-5,5,10,10-tetraphenyl-5,10-dihydroindeno[2,1-a]indene
  参考文献：
  名称：

  Blue fluorescent dihydro-indenoindene derivatives with unusual low oxidation potentials as multifunctional OLED materials

  摘要：

  蓝色荧光双(二芳胺)二氢吲哚吲哚衍生物被合成为多功能OLED的候选材料。

  DOI：

  10.1039/c3tc32245a

文献信息

• White electroluminescence generated by a blend of bis(di-p-tolylamino)dihydroindenoindene and DCJTB
  作者：P.-Y. Shen、S.-H. Wu、Y.-T. Huang、Y. Wei

  DOI：10.1007/s11164-014-1597-6

  日期：2014.7

  Structural analysis and photophysical study of bis(di-p-tolylamino)dihydroindenoindene were conducted. On the basis of its bi-functional property, a simple WOLED was fabricated in the host–guest configuration. White light fluorescence obtained from a single device was generated by two components emitting simultaneously, via an energy-transfer process.

  研究了双(二-对甲苯胺)二氢茚并茚的结构分析和光物理性质。基于其双功能特性，在主客体配置中制备了一个简单的WOLED。通过能量转移过程，单一器件中同时发射两种组分，产生了白色荧光。
• Three-Dimensionally Homoconjugated Carbon-Bridged Oligophenylenevinylene for Perovskite Solar Cells
  作者：Qifan Yan、Yunlong Guo、Anna Ichimura、Hayato Tsuji、Eiichi Nakamura

  DOI：10.1021/jacs.6b04002

  日期：2016.8.31

  Stabilization of the radical cationic state of a donor molecule by 3-D homoconjugation was probed using a substituted carbon-bridged oligophenylenevinylene backbone (COPV, or 5,5-diarylindeno[2,1-a]indenes). For molecules bearing electron-donating groups as the 5,5-aryl moieties, a one-electron oxidation of the COPV backbone results in delocalization of the cationic charge over the whole molecule with

  使用取代的碳桥联低聚亚苯基亚乙烯基主链（COPV，或 5,5-二芳基茚并 [2,1-a] 茚）探测了通过 3-D 同共轭稳定供体分子的自由基阳离子状态。对于带有供电子基团作为 5,5-芳基部分的分子，COPV 主链的单电子氧化导致整个分子上的阳离子电荷离域，重组能量很小。通过 3-D 同共轭形成稳定自由基阳离子的化合物产生均匀的非晶薄膜，并显示出高短路电流、高填充因子，因此当用作有机 - 无机杂化物的空穴传输层时具有高功率转换效率铅钙钛矿太阳能电池。因此，这种材料在空气中的性能和稳定性与使用基准材料获得的性能和稳定性相当，