10,10'-(hexane-1,6-diyl)bis(10H-phenothiazine-3-carbaldehyde) | 636558-38-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 10,10'-(hexane-1,6-diyl)bis(10H-phenothiazine-3-carbaldehyde)
• 英文别名: 10-[6-(3-Formyl-10H-10-phenothiazinyl)hexyl]-10H-3-phenothiazine carbaldehyde；10-[6-(3-formylphenothiazin-10-yl)hexyl]phenothiazine-3-carbaldehyde
• CAS: 636558-38-8
• 化学式: C₃₂H₂₈N₂O₂S₂
• 分子量: 536.719
• InChiKey: NBGLUMFFQNVBGK-UHFFFAOYSA-N

物化性质

• 沸点：
  755.3±60.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  91.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  10,10'-(hexane-1,6-diyl)bis(10H-phenothiazine-3-carbaldehyde) 、 氰乙酸 在 哌啶 、 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 12.0h， 以42%的产率得到3,3'-(10,10'-(hexane-1,6-diyl)bis(10H-phenothiazine-10,3-diyl))bis(2-cyanoacrylic acid)
  参考文献：
  名称：

  Enhancement of photovoltaic performance in dye-sensitized solar cells fabricated with dendritic photosensitizer containing site-isolated chromophores

  摘要：

  We designed and synthesized a series of phenothiazine-based donor acceptor type molecules which consist of different numbers of chromophores in a molecule for use as photosensitizers for dye-sensitized solar cells (DSSCs). Intriguingly, a dendritic molecule containing three chromophores not only gave a new possibility to modify the three dimensional structure, but also reduced aggregation between chromophores inducing dipole dipole interaction. The DSSCs made of a dendritic photosensitizer system exhibited much higher cell efficiencies than those with the single- or double-chromophoric photosensitizers due to efficient electron extraction pathways in the dendritic molecule which lead to a significantly reduce recombination rate of electrons from the TiO2 to the electrolyte when the same numbers of chromophores were loaded on the TiO2 surface. In particular, the DSSC based on the dendritic molecule exhibited improved open-circuit voltage than that of the single- or double-chromophoric photosensitizers. This can be attributed to strong adsorption properties of the TiO2 electrode and a screening effect to the electrolyte ions provided by the network structure of the dendritic photosensitizer. The different behavior of these DSSCs was explained by comparing the results of electrochemical impedance spectroscopy and measurement of open-circuit voltage decay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.08.005
• 作为产物：
  描述：

  吩噻嗪 在 sodium hydride 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 10,10'-(hexane-1,6-diyl)bis(10H-phenothiazine-3-carbaldehyde)
  参考文献：
  名称：

  Enhancement of photovoltaic performance in dye-sensitized solar cells fabricated with dendritic photosensitizer containing site-isolated chromophores

  摘要：

  We designed and synthesized a series of phenothiazine-based donor acceptor type molecules which consist of different numbers of chromophores in a molecule for use as photosensitizers for dye-sensitized solar cells (DSSCs). Intriguingly, a dendritic molecule containing three chromophores not only gave a new possibility to modify the three dimensional structure, but also reduced aggregation between chromophores inducing dipole dipole interaction. The DSSCs made of a dendritic photosensitizer system exhibited much higher cell efficiencies than those with the single- or double-chromophoric photosensitizers due to efficient electron extraction pathways in the dendritic molecule which lead to a significantly reduce recombination rate of electrons from the TiO2 to the electrolyte when the same numbers of chromophores were loaded on the TiO2 surface. In particular, the DSSC based on the dendritic molecule exhibited improved open-circuit voltage than that of the single- or double-chromophoric photosensitizers. This can be attributed to strong adsorption properties of the TiO2 electrode and a screening effect to the electrolyte ions provided by the network structure of the dendritic photosensitizer. The different behavior of these DSSCs was explained by comparing the results of electrochemical impedance spectroscopy and measurement of open-circuit voltage decay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.08.005

文献信息

• Synthesis and characterization of Y‐type polymers for second‐order nonlinear optical applications
  作者：Balakrishna Kolli、Sarada P. Mishra、Akshaya K. Palai、Tapan Kanai、M. P. Joshi、S. Raj Mohan、T. S. Dhami、L. M. Kukreja、A. B. Samui

  DOI：10.1002/pola.26439

  日期：2013.2.15

  dicyanomethylene‐substituted polymers having Y‐type molecular architecture were synthesized by Knoevenagel condensation reaction. The polymers were found to be soluble in organic solvents like tetrahydrofuran and chloroform. From gel permeation chromatography, the molecular weights of the polymers were found to be in the range of 15,300–33,800 g/mol. Thermal analysis showed that the polymers were stable up to

  通过Knoevenagel缩合反应合成了一系列具有Y型分子结构的二氰基亚甲基取代的聚合物。发现该聚合物可溶于有机溶剂，例如四氢呋喃和氯仿。通过凝胶渗透色谱法，发现聚合物的分子量在15,300–33,800 g / mol的范围内。热分析表明，该聚合物在玻璃化转变温度（T g）的温度范围是129–212°C。发现这些聚合物形成良好的光学质量膜。计算得出的阶跃参数在0.01-0.48的范围内。原子力显微镜检查显示，极化后偶极子排列导致形态显着变化。利用1064nm的Nd：YAG激光，研究了二次谐波产生强度的角度依赖性和温度依赖性。计算了几何结构的优化，聚合物的形状以及受体和供体取代基（推挽系统）之间的受限扭转角。©2012 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2013年
• Organophotoreceptors with a charge transport material having multiple vinyl-containing hydrazone groups
  申请人：Grazulevicius V. Juozas

  公开号：US20060078351A1

  公开（公告）日：2006-04-13

  Improved organophotoreceptor comprises an electrically conductive substrate and a photoconductive element on the electrically conductive substrate, the photoconductive element comprising: (a) a charge transport material having the formula where Y comprises an aromatic group; V 1 and V 2 comprise, each independently, a vinyl containing group; and R 1 , R 2 , R 3 , and R 4 comprise, each independently, H, an alkyl group, an acyl group, an ether group, an ester group, an alkenyl group, an alkynyl group, a heterocyclic group, an aromatic group, or a part of a ring group; and (b) a charge generating compound. Corresponding electrophotographic apparatuses, electrophotographic imaging methods, and charge transport materials are also described.

  改进的有机光接收器包括一个电导底板和位于电导底板上的光电导元件，光电导元件包括：（a）具有下述结构的电荷传输材料，其中Y包括芳香族基团；V1和V2分别独立地包括含乙烯基团的基团；R1、R2、R3和R4分别独立地包括H、烷基、酰基、醚基、酯基、烯基、炔基、杂环基、芳香族基团或环基的一部分；以及（b）一个电荷生成化合物。还描述了相应的静电复印设备、静电复印成像方法和电荷传输材料。
• Novel charge transport materials having heteroaromatic hydrazone groups
  申请人：——

  公开号：US20040241563A1

  公开（公告）日：2004-12-02

  An improved organophotoreceptor includes an electrically conductive substrate and a photoconductive element on the electrically conductive substrate where the photoconductive element comprises: a) a charge transport material having the following formula: 1 where X is a linking group; Y 1 and Y 2 are, each independently, a phenothiazine group, a phenoxazine group, or a phenazine group; R 1 , R 2 , R 3 , and R 4 are, each independently, an alkyl group, an alkenyl group, a heterocyclic group, or an aromatic group; and R 5 and R 6 are, each independently, a hydrogen, an alkyl group, an alkenyl group, a heterocyclic group, or an aromatic group; and (b) a charge generating compound. Corresponding electrophotographic apparatuses and imaging methods are described.

  一种改进的有机光感受器包括导电基板和导电基板上的光电导元件，其中光电导元件包括： a) 具有下式的电荷传输材料： 1 其中 X 为连接基团； Y 1 和 Y 2 各自独立地为吩噻嗪基团、吩嗪基团或吩嗪基团； R 1 , R 2 , R 3 和 R 4 各自独立地为烷基、烯基、杂环基或芳香基；以及 R 5 和 R 6 各自独立地是氢、烷基、烯基、杂环基团或芳香基团；及 (b) 产生电荷的化合物。 描述了相应的电致发光装置和成像方法。
• Enhanced Performance of the Dye-Sensitized Solar Cells with Phenothiazine-Based Dyes Containing Double D−A Branches
  作者：Derong Cao、Jinan Peng、Yanping Hong、Xiaoming Fang、Lingyun Wang、Herbert Meier

  DOI：10.1021/ol2000167

  日期：2011.4.1

  Double donor-acceptor (D-A) branched dyes (DBD) with a phenothiazine unit as electron donor and a 2-cyanoacrylic acid unit as electron acceptor were synthesized and used as sensitizers for solar cells (DSSCs). The conversion efficiency of the DSSCs amounts up to 4.22% (2.91% for the single D-A branched dye) under AM 1.5 G irradiation. The results show that the performance of DSSCs can be effectively enhanced by the cooperation of two donor-acceptor containing branches in one molecule of the dyes.
• US7189483B2
  申请人：——

  公开号：US7189483B2

  公开（公告）日：2007-03-13