(E)-1,2-bis(3,4-dihexylthienyl)ethylene | 211998-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (E)-1,2-bis(3,4-dihexylthienyl)ethylene
• 英文别名: 2-[(E)-2-(3,4-dihexylthiophen-2-yl)ethenyl]-3,4-dihexylthiophene
• CAS: 211998-65-1
• 化学式: C₃₄H₅₆S₂
• 分子量: 528.951
• InChiKey: UYXHJKOCSFAVKA-OCEACIFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.5
• 重原子数：
  36
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1,2-bis(3,4-dihexylthienyl)ethylene 在 草酰氯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-[(E)-2-(3,4-Dihexyl-thiophen-2-yl)-vinyl]-3,4-dihexyl-thiophene-2-carbonyl chloride
  参考文献：
  名称：

  Supramolecular Control of Oligothienylenevinylene−Fullerene Interactions:  Evidence for a Ground-State EDA Complex

  摘要：

  Complementary hydrogen-bonding interactions between a barbituric acid-substituted fullerene derivative (1) and corresponding receptor (2) bearing thienylenevinylene units are used to assemble a 1:1 supramolecular complex (K = 5500 M-1). Due to the close proximity of the redox-active moieties within the assembly, strong ground-state electron-donor-acceptor interactions are observed. Photoinduced electron transfer from electron-rich thienylenevinylene subunits to the fullerene is very fast (k(et) = 5.5 x 10(12) s(-1)), as determined by fs-time-resolved transient absorption spectroscopy.

  DOI：

  10.1021/ol047527r
• 作为产物：
  描述：

  3,4-二己基噻吩 在 吡啶 、 四氯化钛 、 锌 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-1,2-bis(3,4-dihexylthienyl)ethylene
  参考文献：
  名称：

  Fulleropyrrolidine-oliththienylenevinylenevinylene-ferrocene triads的合成和光诱导的分子内过程。

  摘要：

  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。

  DOI：

  10.1002/chem.200601889

文献信息

• Synthesis and Characterization of the Electronic and Electrochemical Properties of Thienylenevinylene Oligomers with Multinanometer Dimensions
  作者：Isabelle Jestin、Pierre Frère、Nicolas Mercier、Eric Levillain、Didier Stievenard、Jean Roncali

  DOI：10.1021/ja980603z

  日期：1998.8.1

  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.
• 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.
• 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。
• Supramolecular Control of Oligothienylenevinylene−Fullerene Interactions:  Evidence for a Ground-State EDA Complex
  作者：Nathan D. McClenaghan、Zacharias Grote、Karine Darriet、Michael Zimine、René M. Williams、Luisa De Cola、Dario M. Bassani

  DOI：10.1021/ol047527r

  日期：2005.3.1

  Complementary hydrogen-bonding interactions between a barbituric acid-substituted fullerene derivative (1) and corresponding receptor (2) bearing thienylenevinylene units are used to assemble a 1:1 supramolecular complex (K = 5500 M-1). Due to the close proximity of the redox-active moieties within the assembly, strong ground-state electron-donor-acceptor interactions are observed. Photoinduced electron transfer from electron-rich thienylenevinylene subunits to the fullerene is very fast (k(et) = 5.5 x 10(12) s(-1)), as determined by fs-time-resolved transient absorption spectroscopy.