4-bromo-N,N-bis(4-(hexylthio)phenyl)aniline | 1354780-55-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-bromo-N,N-bis(4-(hexylthio)phenyl)aniline
• 英文别名: 4-bromo-N,N-di(4-hexylthiophenyl)aniline
• CAS: 1354780-55-4
• 化学式: C₃₀H₃₈BrNS₂
• 分子量: 556.674
• InChiKey: DTBHBZBPUWSLJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.26
• 重原子数：
  34.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-bromo-N,N-bis(4-(hexylthio)phenyl)aniline 在 四(三苯基膦)钯 、 sodium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 反应 23.0h， 生成 5-(4-(bis(4-(hexylthio)phenyl)amino)phenyl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  Atomic Level Resolution of Dye Regeneration in the Dye-Sensitized Solar Cell

  摘要：

  Two donor-acceptor organic dyes have been synthesized that differ only by a two-heteroatom change from oxygen to sulfur within the donor unit. The two dyes, (E)-3-(5-(4-(bis(4-(hexyloxy)phenyl)amino)phenyl)thiophen-2-yl)-2-cyanoprop-2-enoic acid (Dye-O) and (E)-3-(5-(4-(bis(4-(hexylthio)phenyl)amino)phenyl)thiophen-2-yl)-2-cyanoprop-2-enoic acid) (Dye-S), were tested in solar cell devices employing both I-3(-)/I--based and [Co(bpy)(3)](3+/2+) redox mediators. Power conversion efficiencies over 6% under simulated AM 1.5 illumination (1 Sun) were achieved in both electrolytes. Despite similar optical and redox properties for the two dyes, a consistently higher open-circuit voltage (V-oc) was measured for Dye-S relative to Dye-O. The improved efficiency observed with Dye-S in an iodide redox mediator is against the commonly held view that sulfur atoms promote charge recombination attributed to inner-sphere interactions. Detailed mechanistic studies revealed that this is a consequence of a 25-fold enhancement of the regeneration rate constant that enhances the regeneration yield under open circuit conditions. The data show that a high short circuit photocurrent does not imply optimal regeneration efficiency as is often assumed.

  DOI：

  10.1021/ja311640f
• 作为产物：
  描述：

  二溴三苯胺 在 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 44.0h， 生成 4-bromo-N,N-bis(4-(hexylthio)phenyl)aniline
  参考文献：
  名称：

  Atomic Level Resolution of Dye Regeneration in the Dye-Sensitized Solar Cell

  摘要：

  Two donor-acceptor organic dyes have been synthesized that differ only by a two-heteroatom change from oxygen to sulfur within the donor unit. The two dyes, (E)-3-(5-(4-(bis(4-(hexyloxy)phenyl)amino)phenyl)thiophen-2-yl)-2-cyanoprop-2-enoic acid (Dye-O) and (E)-3-(5-(4-(bis(4-(hexylthio)phenyl)amino)phenyl)thiophen-2-yl)-2-cyanoprop-2-enoic acid) (Dye-S), were tested in solar cell devices employing both I-3(-)/I--based and [Co(bpy)(3)](3+/2+) redox mediators. Power conversion efficiencies over 6% under simulated AM 1.5 illumination (1 Sun) were achieved in both electrolytes. Despite similar optical and redox properties for the two dyes, a consistently higher open-circuit voltage (V-oc) was measured for Dye-S relative to Dye-O. The improved efficiency observed with Dye-S in an iodide redox mediator is against the commonly held view that sulfur atoms promote charge recombination attributed to inner-sphere interactions. Detailed mechanistic studies revealed that this is a consequence of a 25-fold enhancement of the regeneration rate constant that enhances the regeneration yield under open circuit conditions. The data show that a high short circuit photocurrent does not imply optimal regeneration efficiency as is often assumed.

  DOI：

  10.1021/ja311640f

文献信息

• Thiazolo[5,4-d]thiazole-based organic sensitizers with strong visible light absorption for transparent, efficient and stable dye-sensitized solar cells
  作者：Alessio Dessì、Massimo Calamante、Alessandro Mordini、Maurizio Peruzzini、Adalgisa Sinicropi、Riccardo Basosi、Fabrizia Fabrizi de Biani、Maurizio Taddei、Daniele Colonna、Aldo di Carlo、Gianna Reginato、Lorenzo Zani

  DOI：10.1039/c5ra03530a

  日期：——

  absorption. As a consequence, the dyes were particularly suitable for application in thin layer dye-sensitized solar cells (TiO2 thickness: 3.0–6.5 μm). Small-scale (0.25 cm2) devices prepared using standard materials and fabrication techniques gave power conversion efficiencies up to 7.71%, surpassing those obtained with two different reference dyes. Transparent larger area cells (3.6 cm2) also showed good

  通过计算分析，合成和表征设计了少量的噻唑并[5,4 - d ]噻唑基D–π–A有机染料，在π-间隔基中赋予了双-戊基丙烯二氧噻吩（ProDOT）部分。 。除电子贫乏的噻唑并噻唑单元外，还存在庞大且富电子的ProDOT基团，可诱导最佳的理化性质，包括广泛且强烈的可见光吸收。因此，这种染料特别适合用于薄层染料敏化太阳能电池（TiO 2厚度：3.0–6.5μm）。小规模（0.25 cm 2使用标准材料和制造技术制备的器件的功率转换效率高达7.71％，超过了使用两种不同参考染料获得的功率转换效率。透明的较大面积的样品池（3.6 cm 2）也显示出高达6.35％的良好η值，不需要使用助吸附剂，并且在85°C的温度下存储1000小时仍保持其初始效率。这些结果使这一新的有机敏化剂系列有望成为成功用于建筑集成光伏产品的高效，稳定透明DSSC的候选产品。
• Extending the Conjugation of Pechmann Lactone Thienyl Derivatives: A New Class of Small Molecules for Organic Electronics Application
  作者：Massimo Calamante、Gianna Reginato、Alessio Dessì、Matteo Bartolini、Lorenzo Zani、Alessandro Mordini

  DOI：10.1055/s-0036-1591856

  日期：2018.3

  Pechmann core. The absorption and emission spectra of the new molecules obtained have been recorded in solution and clearly show how their photophysical properties can be modulated by a proper choice of the (hetero)aromatic terminal groups. The compounds prepared in this study (or close analogues thereof) have interesting optical properties and could find application as semiconductors in organic electronics

  摘要 一些含有双取代（E的对称小分子的制备和光谱学表征。）-3,3'-双呋喃基亚砜-2,2'-二酮生色团（所谓的Pechmann内酯）被报道并具有扩展的缀合。此类化合物的合成方法基于Stille–Migita偶联反应，该反应在非常温和的条件下进行，适用于非常敏感的Pechmann核。得到的新的分子的吸收和发射光谱已被记录在溶液中并清楚地示出如何其光物理性质可通过（杂）的适当选择的芳香族末端基团进行调制。这项研究中制备的化合物（或其紧密类似物）具有令人感兴趣的光学性质，可以作为有机电子中的半导体或近红外荧光染料应用。 一些含有双取代（E的对称小分子的制备和光谱学表征。）-3,3'-双呋喃基亚砜-2,2'-二酮生色团（所谓的Pechmann内酯）被报道并具有扩展的缀合。此类化合物的合成方法基于Stille–Migita偶联反应，该反应在非常温和的条件下进行，适用于非常敏感的Pechmann核。