10-(4-methoxyphenyl)-10H-phenoxazine-3-carbaldehyde

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 10-(4-methoxyphenyl)-10H-phenoxazine-3-carbaldehyde
• 英文别名: 10-(4-Methoxyphenyl)phenoxazine-3-carbaldehyde；10-(4-methoxyphenyl)phenoxazine-3-carbaldehyde
• 化学式: C₂₀H₁₅NO₃
• 分子量: 317.344
• InChiKey: ODHHNSSOAMJAGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10-(4-methoxyphenyl)-10H-phenoxazine-3-carbaldehyde 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 26.35h， 生成 (E)-5-(2-(10-(4-methoxyphenyl)-10H-phenoxazin-3-yl)vinyl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  Comparative studies on structure–nonlinearity relationships in a series of novel second-order nonlinear optical chromophores with different aromatic amine donors

  摘要：

  A series of second-order nonlinear optical chromophores containing an identical pi-bridge and electron acceptor but different, aromatic amine electron-donating groups have been synthesized and systematically investigated. The donors studied here include traditional donors carbazole, triphenylamine and N,N-diethylaniline and novel donor phenothiazine, phenoxazine and N-(4-methoxyphenyl)phenoxazine. The ultraviolet absorption, solvatochromic, redox properties, density functional theory calculations, thermal stabilities and electro-optic activities of these chromophores were systematically studied to compare the strength of the donors and illustrate the structure-performance relationships within six chromophores. The results show that the new donors have stronger electron-donating ability than traditional donors. Moreover, they show reduced energy gap, much larger molecular quadratic hyperpolarizability (mu beta) and r(33) value. Exemplified by the N-(4-methoxyphenyl)phenoxazine chromophore, it showed nearly three times higher mu beta and more than four times higher r(33) value than that of the N-hexylcarbazole containing chromophore. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.05.003
• 作为产物：
  描述：

  吩噁嗪 在 copper bronze 、 18-冠醚-6 、 potassium carbonate 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 、 邻二氯苯 为溶剂， 反应 96.0h， 生成 10-(4-methoxyphenyl)-10H-phenoxazine-3-carbaldehyde
  参考文献：
  名称：

  引入官能团对吩恶嗪类染料敏化太阳能电池性能的影响

  摘要：

  合成了具有己氧基链和呋喃部分的苯并恶嗪染料，并将其用于染料敏化太阳能电池。设计染料是为了研究这些取代基对染料的光物理和电化学性质以及对电池光伏性能的影响。引入的己氧基部分作为额外的供体，分别通过增加光吸收和空间位阻来改善电池的短路电流和开路电压。以苯并恶嗪染料为桥单元引入的呋喃部分导致吸收带的红移和大量染料的吸附，从而增加了电池的短路电流。在合成的染料中，具有呋喃部分的染料表现出最佳的转化效率，为6.34％。

  DOI：

  10.1016/j.dyepig.2018.11.010

文献信息

• The effects of the number of anchoring groups and N-substitution on the performance of phenoxazine dyes in dye-sensitized solar cells
  作者：Woosung Lee、Sim Bum Yuk、Jun Choi、Hae Jung Kim、Hyun Woo Kim、Se Hun Kim、Boeun Kim、Min Jae Ko、Jae Pil Kim

  DOI：10.1016/j.dyepig.2013.10.005

  日期：2014.3

  sensitizers were synthesized and applied to dye-sensitized solar cells. Cyanoacrylic acid as an additional anchoring group was introduced to the phenoxazine for efficient electron extraction from the donor part, and an N-substituent was added to suppress dye aggregation. The photophysical, electrochemical and photovoltaic properties of the solar cells based on these dyes were investigated to study the effects

  合成了四种新型的基于苯恶嗪的有机敏化剂，并将其应用于染料敏化太阳能电池。将氰基丙烯酸作为附加的锚定基团引入苯恶嗪中，以从供体部分高效电子提取，并添加N-取代基以抑制染料聚集。研究了基于这些染料的太阳能电池的光物理，电化学和光伏特性，以研究这些取代基对染料敏化太阳能电池性能的影响。附加的氰基丙烯酸受体改善了短路吸收电流，因为它扩大了染料的吸收范围，尽管它也提高了复合率。该ñ-甲氧基苯基单元减少电荷复合，导致更高的开路电压。然而，庞大的取代基减少了在TiO 2上吸收的染料的量。结果，用四种染料制成的电池显示出相似的总转化效率，并且在这些电池中，基于N -4-甲氧基苯基单氰基丙烯酸酯取代的染料的太阳能电池显示出最高的转换效率，为5.09％（短路）电流= 10.11 mA / cm 2，开路电压= 690 mV，填充系数= 72.23％，在AM 1.5G条件下的总转换效率= 5.09％。
• Effects of introducing functional groups on the performance of phenoxazine-based dye-sensitized solar cells
  作者：Jong Hyuk Bae、Seung Ju Lim、Jun Choi、Sim Bum Yuk、Jin Woong Namgoong、Jae Hoon Ko、Woosung Lee、Jae Pil Kim

  DOI：10.1016/j.dyepig.2018.11.010

  日期：2019.3

  Phenoxazine dyes with a hexyloxy chain and furan moiety were synthesized and used in dye-sensitized solar cells. The dyes were designed to investigate the effects of these substituents on the photophysical and electrochemical properties of the dyes and on cell photovoltaic performance. The introduced hexyloxy moiety, as an additional donor, improved the short-circuit current and open-circuit voltage

  合成了具有己氧基链和呋喃部分的苯并恶嗪染料，并将其用于染料敏化太阳能电池。设计染料是为了研究这些取代基对染料的光物理和电化学性质以及对电池光伏性能的影响。引入的己氧基部分作为额外的供体，分别通过增加光吸收和空间位阻来改善电池的短路电流和开路电压。以苯并恶嗪染料为桥单元引入的呋喃部分导致吸收带的红移和大量染料的吸附，从而增加了电池的短路电流。在合成的染料中，具有呋喃部分的染料表现出最佳的转化效率，为6.34％。
• Comparative studies on structure–nonlinearity relationships in a series of novel second-order nonlinear optical chromophores with different aromatic amine donors
  作者：Fenggang Liu、Yuhui Yang、Haoran Wang、Jialei Liu、Chaolei Hu、Fuyang Huo、Shuhui Bo、Zhen Zhen、Xinhou Liu、Ling Qiu

  DOI：10.1016/j.dyepig.2015.05.003

  日期：2015.9

  A series of second-order nonlinear optical chromophores containing an identical pi-bridge and electron acceptor but different, aromatic amine electron-donating groups have been synthesized and systematically investigated. The donors studied here include traditional donors carbazole, triphenylamine and N,N-diethylaniline and novel donor phenothiazine, phenoxazine and N-(4-methoxyphenyl)phenoxazine. The ultraviolet absorption, solvatochromic, redox properties, density functional theory calculations, thermal stabilities and electro-optic activities of these chromophores were systematically studied to compare the strength of the donors and illustrate the structure-performance relationships within six chromophores. The results show that the new donors have stronger electron-donating ability than traditional donors. Moreover, they show reduced energy gap, much larger molecular quadratic hyperpolarizability (mu beta) and r(33) value. Exemplified by the N-(4-methoxyphenyl)phenoxazine chromophore, it showed nearly three times higher mu beta and more than four times higher r(33) value than that of the N-hexylcarbazole containing chromophore. (C) 2015 Elsevier Ltd. All rights reserved.