(E,E,E)-1,2-bis[5-(5'-formyl-3',4'-dihexyl-2'-thienylvinyl)-2-(3,4-dihexylthienyl)]ethylene | 211998-71-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E,E,E)-1,2-bis[5-(5'-formyl-3',4'-dihexyl-2'-thienylvinyl)-2-(3,4-dihexylthienyl)]ethylene
• 英文别名: 5-[(E)-2-[5-[(E)-2-[5-[(E)-2-(5-formyl-3,4-dihexylthiophen-2-yl)ethenyl]-3,4-dihexylthiophen-2-yl]ethenyl]-3,4-dihexylthiophen-2-yl]ethenyl]-3,4-dihexylthiophene-2-carbaldehyde
• CAS: 211998-71-9
• 化学式: C₇₂H₁₁₂O₂S₄
• 分子量: 1137.94
• InChiKey: OVUOOYKUNZQAGH-RSULIEHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  31
• 重原子数：
  78
• 可旋转键数：
  48
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Zn(II)-5-[4-(diethoxyphosphorylmethyl)phenyl]-10,15,20-trimesitylporphyrin 、 (E,E,E)-1,2-bis[5-(5'-formyl-3',4'-dihexyl-2'-thienylvinyl)-2-(3,4-dihexylthienyl)]ethylene 以54%的产率得到
  参考文献：
  名称：

  High effectiveness of oligothienylenevinylene as molecular wires in Zn-porphyrin and C60 connected systems

  摘要：

  已发现 Zn-卟啉和 C60 的激发单线态之间通过低聚噻吩亚乙烯基桥发生光诱导能量转移和电子转移过程，具体取决于低聚噻吩的长度和溶剂极性。

  DOI：

  10.1039/b711194k
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 (E,E,E)-1,2-bis[5-(3',4'-dihexylthienyl(2-vinyl))(3,4-dihexyl-2-thienyl)]ethylene 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 以92%的产率得到(E,E,E)-1,2-bis[5-(5'-formyl-3',4'-dihexyl-2'-thienylvinyl)-2-(3,4-dihexylthienyl)]ethylene
  参考文献：
  名称：

  Synthesis and Characterization of the Electronic and Electrochemical Properties of Thienylenevinylene Oligomers with Multinanometer Dimensions

  摘要：

  Soluble thienylenevinylene oligomers based on 3,4-dihexylthiophene with chain length approaching 100 Angstrom (16-mer) have been synthesized, Optical data obtained in solution and on solution-processed thin films show that chain extension produces a narrowing of the HOMO-LUMO gap (Delta E) and band gap (E-g) which reach values significantly smaller than that of the parent polymer. Plots of Delta E and E-g vs the reciprocal number of carbons in the chain (1/Cn) reveal a deviation from Linearity beyond the 10-12-mer suggesting a limit of convergence around the 20-22-mer. Cyclic voltammetry shows that chain lengthening induces a negative shift of the first redox potential, an increase of the number of accessible redox states, and a decrease of the Coulombic repulsion in multicationic species. Thus, the 16-mer can be charged up to the hexacationic state within a 0.60-V potential window. A plot of the potential of the various redox steps vs 1/Cn suggests full coalescence into a single-step process for the 20-22-mar, A single process is indeed observed for solution cast films of 16-mer, and the respective contributions of the intra- and intermolecular mechanisms in the recombination process are discussed.

  DOI：

  10.1021/ja980603z

文献信息

• Electroactive dendritic π-conjugated oligothienylenevinylenes
  作者：Isabelle Jestin、Eric Levillain、Jean Roncali

  DOI：10.1039/a807810f

  日期：——

  Electroactive π-conjugated oligothienylenevinylenes end-capped with dendritic branches of generation one to three have been synthesized.

  具有一至三代树枝状分支端基的电子活性π-共轭寡噻吩基乙烯已经合成。
• Synthesis and Photoinduced Intramolecular Processes of Fulleropyrrolidine–Oligothienylenevinylene–Ferrocene Triads
  作者：Frédéric Oswald、D.-M. Shafiqul Islam、Yasuyuki Araki、Vincent Troiani、Pilar de la Cruz、Andrés Moreno、Osamu Ito、Fernando Langa

  DOI：10.1002/chem.200601889

  日期：2007.5.7

  Two new triads based on N-methylfulleropyrolidine, oligothienylenevinylenes (nTV) and ferrocene (Fc), namely C(60)-nTV-Fc (n=2, 4) have been synthesized. A HOMO-LUMO gap as low as 1.09-1.11 eV was experimentally determined by cyclic voltammetry. In both polar and nonpolar solvents, photoinduced charge-separation (CS) processes in C(60)-nTV-Fc predominantly take place from the singlet excited states

  合成了基于N-甲基全氟吡咯烷的两个新的三单元组，即低聚亚噻吩乙烯撑（nTV）和二茂铁（Fc），即C（60）-nTV-Fc（n = 2，4）。通过循环伏安法实验确定了低至1.09-1.11 eV的HOMO-LUMO间隙。在极性和非极性溶剂中，C（60）-nTV-Fc中的光诱导电荷分离（CS）过程主要是从C（60）和nTV的单重激发态发生的。稳定的和时间分辨的发射光谱表明了这一结果。在C（60）-4TV-Fc的情况下，CS状态由纳秒瞬态吸收光谱指示。在C（60）-2TV-Fc中，尽管CS的过程也可以通过在非极性和极性溶剂中的荧光猝灭来证实，但CS状态的寿命比C（60）-4TV-Fc的寿命短。
• Jestin; Blanchard; Frere, Journal de Chimie Physique et de Physico-Chimie Biologique, 1998, vol. 95, # 6, p. 1266 - 1269
  作者：Jestin、Blanchard、Frere、Roncali

  DOI：——

  日期：——
• Extended Thienylenevinylene Oligomers as Highly Efficient Molecular Wires
  作者：Isabelle Jestin、Pierre Frère、Philippe Blanchard、Jean Roncali

  DOI：10.1002/(sici)1521-3773(19980420)37:7<942::aid-anie942>3.0.co;2-8

  日期：1998.4.20

  A much smaller band gap than in the parent polymer is observed for the π-conjugated hexadecamer 1, which can be reversibly charged up to the hexacation in a small potential range.