10,10'-dihexyl-10H,10'H-3,3'-biphenothiazine-7-carbaldehyde | 405198-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 10,10'-dihexyl-10H,10'H-3,3'-biphenothiazine-7-carbaldehyde
• 英文别名: 10-hexyl-7-(10-hexyl-10H-phenothiazin-3-yl)-10H-phenothiazine-3-carbaldehyde；10-Hexyl-7-(10-hexylphenothiazin-3-yl)phenothiazine-3-carbaldehyde
• CAS: 405198-32-5
• 化学式: C₃₇H₄₀N₂OS₂
• 分子量: 592.869
• InChiKey: CDBUETLKXUQEJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  10,10'-dihexyl-10H,10'H-3,3'-biphenothiazine-7-carbaldehyde 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以76%的产率得到(10,10'-dihexyl-10H,10'H-3,3'-biphenothiazin-7-yl)methanol
  参考文献：
  名称：

  通过合成后接枝在介孔二氧化硅中氨基甲酸酯连接的（低聚）吩噻嗪：荧光氧化还原活性杂化材料

  摘要：

  共价接枝到 MCM-41 或 SBA-15 二氧化硅上的（低聚）吩噻嗪的介孔杂化材料很容易从（低聚）吩噻嗪基氨基甲酸酯制备。根据电子光谱和循环伏安法，吩噻嗪前体显示出有趣的电子特性。所得的电子活性杂化材料显示出荧光，并且可以在轻度氧化时被氧化以产生稳定的自由基 - 阳离子物种。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900332
• 作为产物：
  描述：

  10-己基吩噻嗪 在 四(三苯基膦)钯 、 溴 、 potassium carbonate 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙二醇二甲醚 、 水 、 1,2-二氯乙烷 为溶剂， 反应 68.0h， 生成 10,10'-dihexyl-10H,10'H-3,3'-biphenothiazine-7-carbaldehyde
  参考文献：
  名称：

  Phenothiazinyl Rhodanylidene Merocyanines for Dye-Sensitized Solar Cells

  摘要：

  Phenothiazinyl rhodanylidene acetic acid merocyanine dyes with variable substitution pattern on the peripheral benzene ring were synthesized in good to excellent yields by Knoevenagel condensation of the corresponding phenothiazinyl aldehydes and rhodanine-N-acetic acid. The electronic properties were investigated by cyclic voltammetry, absorption, and fluorescence spectroscopy. Electron releasing substitution leads to an appreciable lowering of the oxidation potential, bathochromic shift of the absorption band, and minimization of the emission quantum yield. Not least as a consequence of these properties, the compounds are interesting for use as chromophores in dye-sensitized solar cells (DSSC). DSSCs were constructed and successfully tested by determining the characteristic parameters such as incident-photon-to-electron conversion efficiency (IPCE), fill factor (FF), and overall efficiency.

  DOI：

  10.1021/jo202608w

文献信息

• Organic dyes containing oligo-phenothiazine for dye-sensitized solar cells
  作者：Yuan Jay Chang、Po-Ting Chou、Yan-Zuo Lin、Motonori Watanabe、Chih-Jen Yang、Tsung-Mei Chin、Tahsin J. Chow

  DOI：10.1039/c2jm35556f

  日期：——

  A series of organic dyes containing oligo-phenothiazine were synthesized and used effectively on the fabrication of dye-sensitized solar cells (DSSCs). In these compounds the phenothiazine moiety functions both as an electron donor and as a π-bridge. These materials exhibit considerably high values of open-circuit voltage (Voc) ranging from 0.78–0.83 V under an AM1.5 solar condition (100 mW cm−2). Two kinds of substituents, i.e., hexyl and hexyloxyphenyl groups, were added onto the N(10) of phenothiazine for comparison. The best device displayed a short-circuit current (Jsc) of 14.3 mA cm−2, an open-circuit voltage (Voc) of 0.83 V, a fill factor (FF) of 0.65, corresponding to an overall conversion efficiency of 7.78%. Their photophysical properties were analyzed with the aid of a time-dependent density functional theory (TDDFT) model with the B3LYP functional. The electronic nature of the devices was further elucidated by using electrochemical impedance spectroscopy.

  合成了一系列含有寡聚苯噻嗪的有机染料，并有效地用于染料敏化太阳能电池（DSSCs）的制造。在这些化合物中，苯噻嗪基团既作为电子给体，又作为π-桥。这些材料在AM1.5太阳条件（100 mW cm−2）下表现出相当高的开路电压（Voc），值范围为0.78–0.83 V。为了比较，两个种类的取代基，即己基和己氧基苯基，被添加到苯噻嗪的N(10)上。最佳器件显示短路电流（Jsc）为14.3 mA cm−2，开路电压（Voc）为0.83 V，填充因子（FF）为0.65，对应的整体转换效率为7.78%。使用带有B3LYP功能的时间依赖密度泛函理论（TDDFT）模型分析了它们的光物理特性。通过使用电化学阻抗谱进一步阐明了器件的电子性质。
• Facile Synthesis of Functionalized Oligophenothiazines via One-Pot Bromine-Lithium Exchange-Borylation-Suzuki Coupling (BLEBS)
  作者：Thomas Müller、Adam Franz

  DOI：10.1055/s-2008-1032118

  日期：——

  The bromine-lithium exchange in bromophenothiazines followed by transmetalation with trimethyl borate and addition of palladium catalyst, 1.2 equivalents of a base, and an aryl halide yields the cross-coupling products in moderate to very good yields.

  在溴吩噻嗪中进行溴-锂交换，然后用硼酸三甲酯进行反金属化，再加入钯催化剂、1.2 个当量的碱和芳基卤化物，就能以中等到非常好的收率得到交叉偶联产物。
• First synthesis and electronic properties of (hetero)aryl bridged and directly linked redox active phenothiazinyl dyads and triads
  作者：C.S Krämer、K Zeitler、T.J.J Müller

  DOI：10.1016/s0040-4039(01)01848-2

  日期：2001.12

  Phenothiazinyl dyads and triads with variable functionalization can be synthesized in good yields by Suzuki coupling with suitable phenothiazinyl boronates. In addition, the structure of the phenylated phenothiazine (6) has been corroborated by an X-ray structure analysis. According to cyclic voltammetry these oligofunctional heterocyclic oligomers are strongly electronically coupled and represent suitable functional units for novel redox active molecular wires. (C) 2001 Elsevier Science Ltd. All rights reserved.
• First syntheses and electronic properties of (oligo)phenothiazine–C60 dyads
  作者：Nadine Bucci、Thomas J.J. Müller

  DOI：10.1016/j.tetlet.2006.09.076

  日期：2006.11

  (Oligo)phenothiazine-C-60 dyads 3 can be readily synthesized by a three-component condensation-cycloaddition of the corresponding (oligo)phenothiazinyl carbaldehydes 1, N-hexyl glycine (2), and C-60. Cyclic voltammetry of 3 and reference compounds 4 shows that the phenothiazinyl moiety (donor) and the fullerene fragment (acceptor) are electronically decoupled in ground state. However, upon UV excitation the phenothiazinyl fluorescence is considerably quenched, presumably as a consequence of a charge separation by an intramolecular photo-induced electron transfer from phenothiazine to fullerene. (c) 2006 Elsevier Ltd. All rights reserved.