5-iodo-3,4-dihexyl-2-thiophencarboxaldehyde | 207600-69-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-iodo-3,4-dihexyl-2-thiophencarboxaldehyde
• 英文别名: 3,4-di-n-hexylthiophene-2-carbaldehyde；3,4-Dihexylthiophene-2-carbaldehyde
• CAS: 207600-69-9
• 化学式: C₁₇H₂₈OS
• 分子量: 280.475
• InChiKey: HBDVNNCZIFGJSA-UHFFFAOYSA-N

物化性质

• 沸点：
  382.7±30.0 °C(Predicted)
• 密度：
  0.972±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-iodo-3,4-dihexyl-2-thiophencarboxaldehyde 在 吡啶 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到(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
• 作为产物：
  描述：

  己基溴化镁 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 5-iodo-3,4-dihexyl-2-thiophencarboxaldehyde
  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

• New acceptor–π-porphyrin–π-acceptor systems for solution-processed small molecule organic solar cells
  作者：Susana Arrechea、Agustín Molina-Ontoria、Ana Aljarilla、Pilar de la Cruz、Fernando Langa、Luis Echegoyen

  DOI：10.1016/j.dyepig.2015.04.037

  日期：2015.10

  Two new conjugated acceptor donor acceptor (A-pi-D-pi-A) compounds having a Zn-porphyrin acting as donor and linked by ethynylenes to one or two units of thienylenevinylene and capped by dicyano-vinylene groups as acceptor units have been synthesized and their photophysical and electrochemical properties were investigated. These compounds were used as donor materials and PC61BM and PC71BM were used as acceptors in solution-processed bulk-heterojunction (BHJ) organic solar cells and the best photoconversion efficiency (PCE) obtained was 3.21%. (C) 2015 Elsevier Ltd. All rights reserved.
• 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.
• Molecular design and synthesis of ruthenium(ii) sensitizers for highly efficient dye-sensitized solar cells
  作者：A. Anthonysamy、Y. Lee、B. Karunagaran、V. Ganapathy、S.-W. Rhee、S. Karthikeyan、K. S. Kim、M. J. Ko、N.-G. Park、M.-J. Ju、J. K. Kim

  DOI：10.1039/c1jm11760b

  日期：——

  We synthesized hydrophobic ruthenium(II) sensitizers (SY-04 and SY-05) with high molar extinction coefficient by extending the π-conjugation of 3,4- or 3-alkylthiophene-substituted bipyridine ligands. Both dyes displayed a remarkably high molar extinction coefficient of 21.7 × 103 M−1 cm−1 arising from red-shift of their metal-to-ligand charge transfer band when compared to a commonly used N3 sensitizer. The solar-to-electrical energy conversion efficiency (η) of the SY-04 based dye-sensitized solar cell (DSC) was 7.70%, which is 27% higher than that (6.05%) of the N3-based DSC under the same cell fabrication conditions. The increased η was attributed to the increase in life time and recombination half-life measured by electrochemical impedance and transition absorption spectroscopy, respectively. Density functional theory and time-dependent density functional theory calculations of two dyes in both gas phase and solution were performed. The calculated values of the highest occupied and the lowest unoccupied molecular orbitals and absorption spectra are in good agreement with the experimental results.

  我们合成了具有高摩尔消光系数的疏水性钌(II)敏化剂（SY-04和SY-05），通过扩展3,4-或3-烷基噻吩取代的双吡啶配体的π-共轭结构。与常用的N3敏化剂相比，这两种染料的金属至配体电荷转移带红移，导致其摩尔消光系数显著提高，达到21.7 × 103 M−1 cm−1。基于SY-04的染料敏化太阳能电池（DSC）的光电能量转换效率（η）为7.70%，比在相同电池制备条件下基于N3的DSC的6.05%高出27%。提高的η归因于通过电化学阻抗和瞬态吸收光谱分别测量的寿命和复合半寿命的增加。我们对两种染料在气相和溶液中进行了密度泛函理论和含时密度泛函理论计算。计算得到的最高占据和最低未占据分子轨道的能级以及吸收光谱与实验结果非常吻合。