4-(bis(4-(hexyloxy)phenyl)amino)benzaldehyde | 1158909-73-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(bis(4-(hexyloxy)phenyl)amino)benzaldehyde
• 英文别名: 4-(4-hexoxy-N-(4-hexoxyphenyl)anilino)benzaldehyde
• CAS: 1158909-73-9
• 化学式: C₃₁H₃₉NO₃
• 分子量: 473.656
• InChiKey: DFXDCOPPHCTGCI-UHFFFAOYSA-N

物化性质

• 沸点：
  607.3±50.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  4-(bis(4-(hexyloxy)phenyl)amino)benzaldehyde 在 trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) 、 potassium tert-butylate 、 三甲胺 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 反应 80.0h， 生成 4-(4-(bis(4-(hexyloxy)phenyl)amino)styryl)-2,5-bis(hexyloxy)benzaldehyde
  参考文献：
  名称：

  Alkyloxy substituted organic dyes for high voltage dye-sensitized solar cell: Effect of alkyloxy chain length on open-circuit voltage

  摘要：

  Three novel organic dyes (SB1, SB2, and SB3) containing 4-(hexyloxy)-N-(4-(hexyloxy)phenyl)-N-phenylaniline as electron donor and cyanoacrylic acid as electron acceptor bridged by alkyloxy (methyl = SB1, propyl = SB2 and hexyl = SB3) substituted p-phenylenevinylene linkers have been synthesized. Density functional theory (DFT) has employed to study electron distribution and intramolecular charge transfer. Increase in alkyl chain length in alkyloxy substituent leads to increase in open-circuit voltage (V-OC), which is found to be related to the increased electron lifetime at open-circuit condition. Under AM 1.5 G 1 sun light illumination (100 mW/cm(2)), an optimized SB3-sensitized cell show a short-circuit photocurrent density (J(SC)) of 12.83 mA/cm(2), an open-circuit voltage (V-OC) of 0.745 V and a fill factor (FF) of 0.64, corresponding to an overall conversion efficiency (eta) of 6.12%. Little degradation in eta observed over 40 days is indicative of long-term stability of the SB-series dyes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.10.014
• 作为产物：
  描述：

  1-己氧基-4-碘苯 在 1,10-菲罗啉 、 copper(l) chloride 、 potassium hydroxide 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 60.0h， 生成 4-(bis(4-(hexyloxy)phenyl)amino)benzaldehyde
  参考文献：
  名称：

  Alkyloxy substituted organic dyes for high voltage dye-sensitized solar cell: Effect of alkyloxy chain length on open-circuit voltage

  摘要：

  Three novel organic dyes (SB1, SB2, and SB3) containing 4-(hexyloxy)-N-(4-(hexyloxy)phenyl)-N-phenylaniline as electron donor and cyanoacrylic acid as electron acceptor bridged by alkyloxy (methyl = SB1, propyl = SB2 and hexyl = SB3) substituted p-phenylenevinylene linkers have been synthesized. Density functional theory (DFT) has employed to study electron distribution and intramolecular charge transfer. Increase in alkyl chain length in alkyloxy substituent leads to increase in open-circuit voltage (V-OC), which is found to be related to the increased electron lifetime at open-circuit condition. Under AM 1.5 G 1 sun light illumination (100 mW/cm(2)), an optimized SB3-sensitized cell show a short-circuit photocurrent density (J(SC)) of 12.83 mA/cm(2), an open-circuit voltage (V-OC) of 0.745 V and a fill factor (FF) of 0.64, corresponding to an overall conversion efficiency (eta) of 6.12%. Little degradation in eta observed over 40 days is indicative of long-term stability of the SB-series dyes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.10.014

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。
• Influence of a D–π–A system through a linked unit of double and triple bonds in a triarylene bridge for dye-sensitised solar cells
  作者：Rui-Yu Huang、Yu-Hsiang Chiu、Yu-Hsuang Chang、Kew-Yu Chen、Pei-Ting Huang、Ting-Hsuan Chiang、Yuan Jay Chang

  DOI：10.1039/c7nj00413c

  日期：——

  Herein, eight metal-free organic dyes (YH-1–YH-8) containing olefin or acetylene as π-spacer linkages in a triarylene bridge were synthesised.

  在此，合成了含有烯烃或乙炔作为π-间隔连接的三芳基桥的八种无金属有机染料（YH-1–YH-8）。
• Synthesis of novel isophorone-based dyes for dye-sensitized solar cells
  作者：Yih-Chun Chen、Yan-Zuo Lin、Yu-Ting Cheng、Yuan Jay Chang

  DOI：10.1039/c5ra17898c

  日期：——

  Four organic dyes containing isophorone as the π-bridge unit were synthesised and their photophysical and electrochemical properties were characterised.

  四种含有异佛酮作为π-桥单元的有机染料被合成，并对它们的光物理和电化学特性进行了表征。
• 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。
• Push–pull type meso-ester substituted BODIPY near-infrared dyes as contrast agents for photoacoustic imaging
  作者：Yong Ni、Ravi Kumar Kannadorai、Sidney W.-K. Yu、Young-Tae Chang、Jishan Wu

  DOI：10.1039/c7ob00965h

  日期：——

  push–pull type meso-ester substituted BODIPY dyes 1–4 with intense near-infrared absorption, largely enhanced photoacoustic (PA) activity and excellent photo-stability were synthesized. The impact of the electronic structure on the PA activity was also discussed. Moreover, the in vitro and in vivo PA imaging were investigated, which suggested a passive targeting capacity in the tumor site.

  一系列推挽型的内消旋-酯取代的BODIPY染料1-4用强的近红外线的吸收，在很大程度上提高光声（PA）活性和优异的光稳定性合成。还讨论了电子结构对PA活性的影响。此外，研究了体外和体内PA成像，这提示了在肿瘤部位的被动靶向能力。