5-[4-(hexyloxy)phenyl]dipyrromethane | 500907-22-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[4-(hexyloxy)phenyl]dipyrromethane
• 英文别名: 2-[(4-hexoxyphenyl)-(1H-pyrrol-2-yl)methyl]-1H-pyrrole
• CAS: 500907-22-2
• 化学式: C₂₁H₂₆N₂O
• 分子量: 322.45
• InChiKey: FFNNBBQIIBDAKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-[4-(hexyloxy)phenyl]dipyrromethane 在 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  BODIPY-based conjugated polymers for broadband light sensing and harvesting applications

  摘要：

  新型低带隙聚合物的合成大大改善了聚合物-富勒烯器件的光传感和光收集性能。本文介绍了基于 4,4-二氟-4-硼杂-3a,4a-二氮杂-s-吲哚烯核（BODIPY）和双（3,4-亚乙二氧基噻吩）（bis-EDOT）或其全硫类似物双（3,4-亚乙二硫噻吩）（bis-EDTT）的两种低带隙聚合物的合成。这些聚合物显示出伏极性电荷传输，并证明其适合在可溶液加工的聚合物-富勒烯装置中用于宽带光传感和太阳能收集。

  DOI：

  10.1039/c2jm32374e
• 作为产物：
  描述：

  溴己烷 在 四丁基碘化铵 、 potassium carbonate 、 三氟乙酸 作用下， 以 丙酮 为溶剂， 反应 16.08h， 生成 5-[4-(hexyloxy)phenyl]dipyrromethane
  参考文献：
  名称：

  Stable negative differential resistance in porphyrin based σ–π–σ monolayers grafted on silicon

  摘要：

  两种Si-卟啉混合单分子层表现出室温负差分电阻（NDR）特性。含有氟苯基卟啉基团的单分子层由于紧密堆积，显示出更好的峰-谷比。

  DOI：

  10.1039/c5ra09484d

文献信息

• Design and synthesis of light-harvesting rods for intrinsic rectification of the migration of excited-state energy and ground-state holesElectronic supplementary information (ESI) available: 1H and 13C NMR spectra for all new porphyrin precursors; 1H NMR and LD-MS spectra for all new porphyrins and porphyrin arrays (LD-MS only for deprotected arrays 12′ and 14′, and pentad 18); analytical SEC data for all porphyrin arrays. See http://www.rsc.org/suppdata/jm/b1/b108168c/
  作者：Robert S. Loewe、Robin K. Lammi、James R. Diers、Christine Kirmaier、David F. Bocian、Dewey Holten、Jonathan S. Lindsey

  DOI：10.1039/b108168c

  日期：2002.4.17

  We present the design of molecular materials for ultimate use in solid-state solar cells. The molecular materials are semi-rigid oligomeric rods of defined length with metalloporphyrins in the backbone and a carboxy group at one end for attachment to a surface. The rods are designed to absorb visible light, and then undergo excited-state energy transfer and ground-state hole transfer in opposite directions along the length of the rod. The rational synthesis of the multiporphyrin arrays relies on joining porphyrin building blocks in an efficient and controlled manner. Several porphyrin building blocks have been synthesized that bear bromophenyl, iodophenyl, trimethylsilylethynylphenyl and/or ethynylphenyl substituents for use in a copper-free Sonogashira reaction using Pd2(dba)3 and P(o-tol)3. Competition experiments performed on equimolar quantities of an iodo-porphyrin and a bromo-porphyrin with an ethynyl-porphyrin show iodo + ethyne coupling with a low amount (35 °C) or undetectable amount (22 °C) of bromo + ethyne coupling. Efficient coupling of bromo-porphyrins with ethynyl-porphyrins was achieved using the same copper-free Sonogashira reaction conditions at higher temperature (50 °C or 80 °C). These findings allow successive coupling reactions to be achieved using substrates bearing iodo and bromo synthetic handles. Thus, a porphyrin-based tetrad (or pentad) was synthesized with a final convergent coupling of a bromo-substituted dyad (or triad) and an ethynyl-substituted dyad. A porphyrin triad was prepared by sequential iodo + ethyne coupling reactions. The triad, tetrad, and pentad each are comprised of a terminal magnesium porphyrin bearing one carboxy group (for surface attachment) and two pentafluorophenyl groups; the remaining porphyrins in each array are present as the zinc chelate. Electrochemical characterization of benchmark porphyrins indicates the presence of the desired electrochemical gradient for hole hopping in the arrays. Static absorption data indicate that the arrays are weakly coupled, while static fluorescence data indicate that the excited-state energy flows in high yield to the terminal magnesium porphyrin. Time-resolved spectroscopic analysis leads to rate constants in THF of (9 ps)−1, (15 ps)−1, and (30 ps)−1 for ZnMg dyad 20, Zn2Mg triad 13, and Zn3Mg tetrad 15, respectively, and quantum efficiencies ≥99% for energy flow to the magnesium porphyrin in each case. These design and synthesis strategies should be useful for the construction of materials for molecular-based solar cells.

  我们介绍了用于固态太阳能电池的终极应用的分子材料的设计。这些分子材料是具有特定长度的半刚性寡聚棒，其骨架中含有金属卟啉，一端带有羧基以附着于表面。这些棒设计用于吸收可见光，然后在棒的长度上沿着相反方向进行激发态能量传递和基态空穴传递。多卟啉阵列的合理合成依赖于以高效且受控的方式连接卟啉构建块。已经合成了几种带有溴苯基、碘苯基、三甲基硅乙炔基苯基和/或乙炔基苯基的卟啉构建块，用于在无铜Sonogashira反应中使用Pd2(dba)3和P(o-tol)3。在等摩尔量的碘卟啉和溴卟啉与乙炔基卟啉的竞争实验中，碘+乙炔偶联在低量（35°C）或无法检测量（22°C）下，而溴+乙炔偶联未发生。在更高温度（50°C或80°C）下，使用相同的无铜Sonogashira反应条件实现了溴卟啉与乙炔基卟啉的高效偶联。这些发现允许使用带有碘和溴合成柄的底物实现连续偶联反应。因此，通过最终的汇聚偶联反应合成具有溴取代的双体（或三体）和乙炔基取代的双体的基于卟啉的四体（或五体）。通过连续的碘+乙炔偶联反应制备了卟啉三体。三体、四体和五体各自由一个末端带有羧基（用于表面附着）和两个五氟苯基的镁卟啉组成；每个阵列中的其余卟啉作为锌螯合物存在。基准卟啉的电化学表征显示了阵列中空穴跳跃所需的电化学梯度的存在。静态吸收数据显示阵列是弱耦合的，而静态荧光数据显示激发态能量高效流向末端镁卟啉。时间分辨光谱分析得出了THF中的速率常数，分别为ZnMg双体20的(9 ps)−1、Zn2Mg三体13的(15 ps)−1和Zn3Mg四体15的(30 ps)−1，且每次能量流向镁卟啉的量子效率≥99%。这些设计和合成策略应有助于构建基于分子的太阳能电池材料。
• Molecular Engineering of Boryl Oxasmaragdyrins through Peripheral Modification: Structure-Efficiency Relationship
  作者：Sandeep B. Mane、Chen-Hsiung Hung

  DOI：10.1002/chem.201405856

  日期：2015.3.16

  Expanded porphyrins with the absorption profile down to the infrared region through increased π‐conjugation are suitable candidates for a low energy sensitizer. Oxasmaragdyrin boron complexes, a class of aromatic‐core‐modified expanded porphyrin with 22 π‐electrons, have been recently utilized as an efficient low energy sensitizer in dye‐sensitized solar cells. In this paper, we have prepared a series

  扩展的卟啉具有通过增加π共轭而吸收到红外区域的吸收特性，是低能敏化剂的合适候选物。Oxasmaragdyrin硼配合物是一类具有22个π电子的芳香核修饰的膨胀卟啉，最近已被用作染料敏化太阳能电池中的一种高效低能敏化剂。在本文中，我们通过外围分子工程制备了一系列八种新颖的硼基草酸三氮杂卟啉，并评估了它们在染料敏化太阳能电池中的总体光伏性能。在光物理，电化学和光伏研究的帮助下，发现分子结构，尤其是供体-受体基团的数量和位置在其光伏性能中起着举足轻重的作用。在UV / Vis光谱的400–500 nm区域中存在两个分离良好的Soret分离带，可确保更广泛的吸收波长范围。即使是两个固定基团的染料（与单锚基染料（SM1 - SM4）相比，SM5 - SM8）与TiO 2的结合力强，后者的光电性能优于前者。染料SM1，用两个己氧基供体和一种羧酸锚显示出4.36％的最佳的整体转换效率（Ĵ SC =10.91毫安厘米-2
• Stable negative differential resistance in porphyrin based σ–π–σ monolayers grafted on silicon
  作者：Kavita Garg、Chiranjib Majumder、Shiv Kumar Gupta、Dinesh Kumar Aswal、Sandip Kumar Nayak、Subrata Chattopadhyay

  DOI：10.1039/c5ra09484d

  日期：——

  Two Si–porphyrin hybrid monolayers showed room temperature negative differential resistance (NDR) property. The monolayer with a fluorophenyl porphyrin moiety showed a better peak-to-valley ratio due to compact packing.

  两种Si-卟啉混合单分子层表现出室温负差分电阻（NDR）特性。含有氟苯基卟啉基团的单分子层由于紧密堆积，显示出更好的峰-谷比。
• BODIPY-based conjugated polymers for broadband light sensing and harvesting applications
  作者：Diego Cortizo-Lacalle、Calvyn T. Howells、Salvatore Gambino、Filipe Vilela、Zuzana Vobecka、Neil J. Findlay、Anto R. Inigo、Stuart A. J. Thomson、Peter J. Skabara、Ifor D. W. Samuel

  DOI：10.1039/c2jm32374e

  日期：——

  The synthesis of novel low band-gap polymers has significantly improved light sensing and harvesting in polymer–fullerene devices. Here the synthesis of two low band-gap polymers based on the 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene core (BODIPY), and either bis(3,4-ethylenedioxythiophene) (bis-EDOT) or its all-sulfur analogue bis(3,4-ethylenedithiathiophene) (bis-EDTT) are described. The polymers demonstrate ambipolar charge transport and are shown to be suitable for broadband light sensing and solar energy harvesting in solution-processable polymer–fullerene devices.

  新型低带隙聚合物的合成大大改善了聚合物-富勒烯器件的光传感和光收集性能。本文介绍了基于 4,4-二氟-4-硼杂-3a,4a-二氮杂-s-吲哚烯核（BODIPY）和双（3,4-亚乙二氧基噻吩）（bis-EDOT）或其全硫类似物双（3,4-亚乙二硫噻吩）（bis-EDTT）的两种低带隙聚合物的合成。这些聚合物显示出伏极性电荷传输，并证明其适合在可溶液加工的聚合物-富勒烯装置中用于宽带光传感和太阳能收集。