diethyl 2-(5-hexylthienyl)methylphosphonate | 609369-55-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl 2-(5-hexylthienyl)methylphosphonate
• 英文别名: diethyl (5-hexylthiophen-2-yl)methylphosphonate；Diethyl(5-hexylthiophen-2-yl)methylphosphonate；2-(diethoxyphosphorylmethyl)-5-hexylthiophene
• CAS: 609369-55-3
• 化学式: C₁₅H₂₇O₃PS
• 分子量: 318.417
• InChiKey: AGTKDXMEWZSJPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-噻吩二甲醛 、 diethyl 2-(5-hexylthienyl)methylphosphonate 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以70%的产率得到(E,E)-2,5-bis[2-(5-hexyl-2-thienyl)-1-ethenyl]thiophene
  参考文献：
  名称：

  Effect of Local Molecular Structure on the Chain-Length Dependence of the Electronic Properties of Thiophene-Based π-Conjugated Systems

  摘要：

  Three series of thiophene-based pi-conjugated oligomers built with different combinations of thiophene cycles and double bonds have been synthesized and characterized. The analysis of the chain length dependence of the electronic, electrochemical, and vibrational properties of the three series of oligomers has been carried out using cyclic voltammetry, UV-vis, IR, and Raman spectroscopies. These various investigations provide consistent results showing that incorporation of ethylenic linkages in an oligothiophene structure leads to a faster decrease of the HOMO-LUMO gap with chain extension due to the combined effects of enhanced planarity and lower overall aromatic character of the system. Although the incorporation of two consecutive double bonds in the system leads to a stabilization of the dicationic state, this structural modification does not produce the expected further decrease of the HOMO-LUMO gap at large chain extension. This phenomenon is discussed on the basis of an interplay between aromaticity and bond length alternation.

  DOI：

  10.1021/jo034319o
• 作为产物：
  描述：

  2-正己基噻吩 、 碘甲基膦酸二乙酯 在 正丁基锂 、 copper(l) iodide 作用下， 生成 diethyl 2-(5-hexylthienyl)methylphosphonate
  参考文献：
  名称：

  Effect of Local Molecular Structure on the Chain-Length Dependence of the Electronic Properties of Thiophene-Based π-Conjugated Systems

  摘要：

  Three series of thiophene-based pi-conjugated oligomers built with different combinations of thiophene cycles and double bonds have been synthesized and characterized. The analysis of the chain length dependence of the electronic, electrochemical, and vibrational properties of the three series of oligomers has been carried out using cyclic voltammetry, UV-vis, IR, and Raman spectroscopies. These various investigations provide consistent results showing that incorporation of ethylenic linkages in an oligothiophene structure leads to a faster decrease of the HOMO-LUMO gap with chain extension due to the combined effects of enhanced planarity and lower overall aromatic character of the system. Although the incorporation of two consecutive double bonds in the system leads to a stabilization of the dicationic state, this structural modification does not produce the expected further decrease of the HOMO-LUMO gap at large chain extension. This phenomenon is discussed on the basis of an interplay between aromaticity and bond length alternation.

  DOI：

  10.1021/jo034319o

文献信息

• Oligothienylenevinylenes incorporating 3,4-ethylenedioxythiophene (EDOT) units
  作者：Mathieu Turbiez、Pierre Frère、Jean Roncali

  DOI：10.1016/j.tet.2005.01.107

  日期：2005.3

  self-rigidification of the conjugated system due to non covalent S⋯O intramolecular interactions. The strong electron donor effect of the EDOT units explains the determining role of the relative position of the EDOT units on the localization and stabilization of the positive charges in the radical cation or dication states.

  Wittig-Horner反应从带有EDOT或bis-EDOT单元的膦酸酯阴离子合成了一系列基于噻吩和EDOT单元以及双键的各种组合的π共轭低聚物。光学和电化学结果证明了EDOT部分对于调节低聚物的电子性能至关重要。由于非共价S = O分子内相互作用，在分子中间插入bis-EDOT单元会导致共轭体系自刚性化。EDOT单元的强电子给体效应解释了EDOT单元相对位置对自由基阳离子或阳离子状态中正电荷的定位和稳定的确定作用。
• Solution-Processed Bulk Heterojunction Photovoltaic Cells from Gradient π-Conjugated Thienylene Vinylene Dendrimers
  作者：Jin-Liang Wang、Chengmei Zhong、Zheng-Ming Tang、Hongbin Wu、Yuguo Ma、Yong Cao、Jian Pei

  DOI：10.1002/asia.200900245

  日期：2010.1.4

  Solution‐processed bulk heterojunction solar cells using these dendrimers as donor and [6,6]‐phenyl‐C61 butyric acid methyl ester as acceptor are prepared and tested. The power conversion efficiency of the devices based on G0-4-2 is 0.40 % under illumination of air mass 1.5 and 100 mW cm−2. This is the highest record value for OTV‐based materials to date. Although the absorption band of dendrimer G0-4-2 is

  很好地合成了一系列基于5,5,10,10,15,15-六己基甲苯部分作为节点和不同长度的低聚亚乙烯基（OTV）单元作为支化臂的梯度π共轭树枝状大分子及其相应模型通过维蒂希-霍纳反应获得产量。所有新化合物的特征均是1 H和13C NMR光谱，元素分析和MALDI-TOF MS或ESI-MS。对它们的光物理性质的研究表明，梯度树突状支架不仅比其相应的模型化合物具有更高的摩尔吸收系数和更宽的吸收区域，而且相对于相应的OTV而言，还提高了PL量子产率。合适的HOMO和LUMO含量以及出色的成膜性能使这些分子成为有机太阳能电池的潜在候选者。使用这些树状聚合物作为供体，并用[6,6]-苯基-C 61丁酸甲酯作为受体，进行溶液处理的整体异质结太阳能电池的制备和测试。基于G0-4-2的设备的电源转换效率在空气质量1.5和100 mW cm -2的照度下，α为0.40％。这是迄今为止基于OTV的材料的最高记