(E)-7-(4-(diphenylamino)styryl)-9,9-dioctyl-9H-fluorene-2-carbaldehyde | 1334306-18-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-7-(4-(diphenylamino)styryl)-9,9-dioctyl-9H-fluorene-2-carbaldehyde
• 英文别名: 9,9-dioctyl-7-[(E)-2-[4-(N-phenylanilino)phenyl]ethenyl]fluorene-2-carbaldehyde
• CAS: 1334306-18-1
• 化学式: C₅₀H₅₇NO
• 分子量: 688.009
• InChiKey: KOBBNVPCCNBEGU-OCEACIFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17
• 重原子数：
  52
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-7-(4-(diphenylamino)styryl)-9,9-dioctyl-9H-fluorene-2-carbaldehyde 在 potassium tert-butylate 、 四丁基溴化铵 、 palladium diacetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 7-((E)-2-(7-(4-(diphenylamino)styryl)-9,9-dioctyl-9H-fluoren-2-yl)vinyl)-9,9-dioctyl-9H-fluorene-2-carbaldehyde
  参考文献：
  名称：

  Fluorenylvinylenes bridged triphenylamine-based dyes with enhanced performance in dye-sensitized solar cells

  摘要：

  We have synthesized a series of new dipolar organic dyes Bn (n=0, 1, 2) employing triarylamine as the electron-donor, 2-cyanoacrylic acid as the electron-acceptor, and fluorenevinylene as the conjugated bridge, which were used as sensitizers in dye-sensitized solar cells. It is found that the solar-energy-to-electricity conversion efficiencies of the prepared DSSCs are in the range of 2.79-5.56%, which reach 35-70% of a standard device based on N719 fabricated and measured under the same conditions. The DSSC sensitized with B1 with balanced length of conjugated bridge shows the highest photo-to-electrical energy conversion efficiency and the open-circuit photovoltage (V-oc) of 0.86 V. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.008
• 作为产物：
  描述：

  N,N-二苯基-4-乙烯基苯胺 、 7-溴-9,9-二辛基芴-2-甲醛 在 四丁基溴化铵 、 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到(E)-7-(4-(diphenylamino)styryl)-9,9-dioctyl-9H-fluorene-2-carbaldehyde
  参考文献：
  名称：

  Fluorenylvinylenes bridged triphenylamine-based dyes with enhanced performance in dye-sensitized solar cells

  摘要：

  We have synthesized a series of new dipolar organic dyes Bn (n=0, 1, 2) employing triarylamine as the electron-donor, 2-cyanoacrylic acid as the electron-acceptor, and fluorenevinylene as the conjugated bridge, which were used as sensitizers in dye-sensitized solar cells. It is found that the solar-energy-to-electricity conversion efficiencies of the prepared DSSCs are in the range of 2.79-5.56%, which reach 35-70% of a standard device based on N719 fabricated and measured under the same conditions. The DSSC sensitized with B1 with balanced length of conjugated bridge shows the highest photo-to-electrical energy conversion efficiency and the open-circuit photovoltage (V-oc) of 0.86 V. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.008

文献信息

• Effect of π-conjugated linkage on photophysical properties: Acetylene linker as the better connection group for highly solvatochromic probes
  作者：Alexis Tigreros、Alejandro Ortiz、Braulio Insuasty

  DOI：10.1016/j.dyepig.2014.05.035

  日期：2014.12

  synthetized and the effects of π-conjugated linkers (vinyl, ethynyl and 1,3-diynyl) on the solvatochromic properties were studied. The fluorescence emission spectra of the dyes were studied using solvents of different polarities, and the influence of specific solvent–solute interactions over emission properties was investigated through Lippert–Mataga model. In particular, we found that compound 2 (with an ethynyl

  基于在三苯基胺和芴（荧光团1 - 3）中synthetized和研究了溶剂化性质的π共轭连接基（乙烯基，乙炔基和1,3-二炔基）的影响。使用不同极性的溶剂研究了染料的荧光发射光谱，并通过Lippert-Mataga模型研究了特定的溶剂-溶质相互作用对发射性能的影响。特别是，我们发现化合物2（具有乙炔基）相对于分别具有乙烯基和1,3-二炔基的化合物1和3表现出显着的优势。它显示出更好的溶剂致变色性（从己烷到CH 3 CN为140 nm ），更高的斯托克斯位移（CH为178 nm）3 CN）和朝向极性溶剂更敏感的量子产率（0.09 DMF -0.98 THF）中，当与那些所述参考探针（普罗丹）进行比较。此外，在相同条件下，该接头表现出更高的抗光脱盐性。通过DFT和TD-DFT对几何和电子跃迁进行了分析，其结果与实验结果相吻合。
• Fluorenylvinylenes bridged triphenylamine-based dyes with enhanced performance in dye-sensitized solar cells
  作者：Huipeng Zhou、Pengchong Xue、Yuan Zhang、Xin Zhao、Junhui Jia、Xiaofei Zhang、Xingliang Liu、Ran Lu

  DOI：10.1016/j.tet.2011.09.008

  日期：2011.11

  We have synthesized a series of new dipolar organic dyes Bn (n=0, 1, 2) employing triarylamine as the electron-donor, 2-cyanoacrylic acid as the electron-acceptor, and fluorenevinylene as the conjugated bridge, which were used as sensitizers in dye-sensitized solar cells. It is found that the solar-energy-to-electricity conversion efficiencies of the prepared DSSCs are in the range of 2.79-5.56%, which reach 35-70% of a standard device based on N719 fabricated and measured under the same conditions. The DSSC sensitized with B1 with balanced length of conjugated bridge shows the highest photo-to-electrical energy conversion efficiency and the open-circuit photovoltage (V-oc) of 0.86 V. (C) 2011 Elsevier Ltd. All rights reserved.