5-(4-(bis(4-(hexyloxy)phenyl)amino)phenyl)thiophene-2-carboxaldehyde | 1148130-98-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(4-(bis(4-(hexyloxy)phenyl)amino)phenyl)thiophene-2-carboxaldehyde
• 英文别名: 5-(4-(bis(4-(hexyloxy)phenyl)amino)-phenyl)thiophene-2-carbaldehyde
• CAS: 1148130-98-6
• 化学式: C₃₅H₄₁NO₃S
• 分子量: 555.781
• InChiKey: GMCSIKFXKBJVDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.62
• 重原子数：
  40.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(4-(bis(4-(hexyloxy)phenyl)amino)phenyl)thiophene-2-carboxaldehyde 在 sodium tetrahydroborate 、 碘 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Organic Dyes Incorporating Oligothienylenevinylene for Efficient Dye-Sensitized Solar Cells

  摘要：

  Two new organic dyes incorporating triphenylamine as a donor and oligothienylenevinylene as a bridge have been synthesized. The new dyes cover the entire visible region and have a power conversion of up to 6.25%.

  DOI：

  10.1021/ol302738k
• 作为产物：
  描述：

  4-(hexyloxy)-N-(4-(hexyloxy)phenyl)-N-phenylaniline 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 氯仿 、 水 、 乙酸乙酯 为溶剂， 反应 47.0h， 生成 5-(4-(bis(4-(hexyloxy)phenyl)amino)phenyl)thiophene-2-carboxaldehyde
  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

• Reversed Y-shape di-anchoring sensitizers for dye sensitized solar cells based on benzimidazole core
  作者：Mulu Berhe Desta、Sumit Chaurasia、Jiann T. Lin

  DOI：10.1016/j.dyepig.2017.01.068

  日期：2017.5

  Three new Y-shaped D-(π-A)2 di-anchoring organic dyes comprising an arylamine as the electron donor, 2-cyanoacrylic acid as electron acceptors and various 2,4,7-trisubstituted benzimidazole entity as the π-linkers/spacers, have been synthesized for dye-sensitized solar cells. The new dyes MD2 and MD3 show red-shifted absorption in solution spectra when compared with their congeners (8b and 9b) without

  三种新型Y形D-（π-A）2双锚定有机染料，包括芳胺作为电子供体，2-氰基丙烯酸作为电子受体和各种2,4,7-三取代的苯并咪唑实体作为π-连接剂/已经合成了用于染料敏化太阳能电池的间隔物。与没有给电子己氧基取代基的同类染料（8b和9b）相比，新染料MD2和MD3在溶液光谱中显示出红移吸收。苯并咪唑的N-烷基虽然有助于改善溶解度，但显然会导致苯并咪唑核心与连接至受体的共轭链段中相邻噻吩环之间的严重扭曲。N-烷基或与芳胺供体连接的苯环。对新染料进行了光物理和电化学测量以及理论计算。除电流电压扫描和入射光子至电子的转换效率（IPCE）外，还进行了电化学阻抗谱（EIS）研究。对于没有和有CDCA共吸附剂的DSSC，染料MD3分别显示出最高的光电能转化效率，分别为6.45％和6.69％。MD3比9b更好的电池性能可以归因于前者更好的光收集和更好的暗电流抑制。
• Push–pull triphenylamine based chromophores as photosensitizers and electron donors for molecular solar cells
  作者：Ana Aljarilla、Cristina Herrero-Ponce、Pedro Atienzar、Susana Arrechea、Pilar de la Cruz、Fernando Langa、Hermenegildo García

  DOI：10.1016/j.tet.2013.05.137

  日期：2013.8

  A series of push–pull chromophores (1–6) comprising triphenylamine as donor and methylenethiazole, bearing electron-withdrawing groups in the 2′ position, as terminal acceptor groups have been developed. The resulting dyes were characterized by UV–vis and fluorescence spectroscopies, cyclic and OSWV voltammetries and thermal analysis. The low energy absorption band of these oligomers was located at

  一系列推挽发色团（1 - 6），其包括三苯基胺作为供体和methylenethiazole，轴承吸电子基团中的2'位置，作为终端受体基团已被开发。通过紫外可见光谱和荧光光谱，循环伏安法和OSWV伏安法以及热分析来表征所得的染料。这些低聚物的低能吸收带位于溶液中的583–705 nm。发现了显着的正溶剂化变色，与KAMlet-Taft常数具有极好的相关性，证实了该谱带的电荷转移特性。理论研究揭示了这些化合物中的一个局部醌型字符和减少的带隙的HOMO-LUMO能量1 - 6发现由电化学和光学测量得到的衍生物适合用作供体材料，并与PCBM组合用作平面异质结太阳能电池中的受体。所研究的器件基于电连接的堆叠式电池，并结合了这些低带隙生色团，在空气质量（AM）1.5G照明下显示出高达0.91％的合理转换效率。
• Imidazole-Based Sensitizers Containing Double Anchors for Dye-Sensitized Solar Cells
  作者：Yung-Sheng Yen、Jen-Shyang Ni、Tse-Yen Lin、Wei-I Hung、Jiann T. Lin、Ming-Chang P. Yeh

  DOI：10.1002/ejoc.201501131

  日期：2015.11

  New imidazole-based organic dyes with two 2-cyanoacetic acid acceptors/anchors connected at the C-4 and C-5 positions, and a carbazole or arylamine donor connected at the C-2 position of the imidazole entity were synthesized and used as sensitizers for dye-sensitized solar cells. The dyes exhibit optical absorption from 300–600 nm with high molar extinction coefficients. The inclusion of a hexyl chain

  合成了新的咪唑基有机染料，在 C-4 和 C-5 位置连接了两个 2-氰基乙酸受体/锚，并在咪唑实体的 C-2 位置连接了咔唑或芳胺供体，并将其用作敏化剂用于染料敏化太阳能电池。染料在 300-600 nm 范围内表现出光吸收，具有高摩尔消光系数。发现在咪唑的氮原子处包含己基链会导致来自咪唑的 C-4 链段发生大的扭曲，因此导致电子注入效率较低。虽然染料聚集导致在较长波长区域捕获光，但它也会导致激发态猝灭并阻碍电子注入。因此，仅实现了中等的 DSSC 转换效率。添加CDCA共吸附剂后，最多可达约。电池效率提高了 30%。添加 50 mM CDCA 后，最佳电池效率达到 4.97 %。