3,4-dihexyloxythiophene-2,5-dicarbaldehyde | 211235-84-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dihexyloxythiophene-2,5-dicarbaldehyde
• 英文别名: 3,4-Dihexoxythiophene-2,5-dicarbaldehyde
• CAS: 211235-84-6
• 化学式: C₁₈H₂₈O₄S
• 分子量: 340.484
• InChiKey: KIAGDLVNFCDGKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(Triphenyl-λ⁵-phosphanylidene)-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester 、 3,4-dihexyloxythiophene-2,5-dicarbaldehyde 以90%的产率得到2,5-bis<4,5-bis(methoxycarbonyl)-2H-1,3-dithiol-2-ylidenemethyl>-3,4-dihexyloxythiophene
  参考文献：
  名称：

  Low Oxidation Potential Tetrathiafulvalene Analogues Based on 3,4-Dialkoxythiophene π-Conjugating Spacers

  摘要：

  Tetrathiafulvalene analogues involving dihexyloxythiophene (1), ethylenedioxythiophene (2), and bis(3,4-dihexyloxy-2-thienyl)ethylene (3) as conjugating spacer and diversely substituted at the 1,3-dithiole ring (R) have been synthesized. Electronic absorption spectra show the expected decrease of HOMO-LUMO gap when increasing the electron-releasing power of R or the length of the conjugating spacer. Cyclic voltammetry (CV) shows that whereas compounds 1 and 2 are reversibly oxidized into their cation radical and dication through two one-electron steps, for compounds 3 the dication is formed directly via a two-electron transfer. Comparison of the data for compounds 2 and 3 with those of their respective analogues based on thiophene and dithienylethylene shows that introduction of the electron-donating alkoxy groups at the 3 and 4 positions of the thiophene ring produces a 150-200 mV negative shift of the first redox potential (E degrees(1)). On the other hand, CV data for compounds 1 and 2 reveal several unusual features such as E degrees(1) approximate to 0.10 V/SCE ranking among-the lowest known to date and a Coulombic repulsion between positive charges in the dication larger than for the analogue ct-donors based on unsubstituted thiophene. These results are interpreted by a major reorganization of the electronic distribution in the donor molecule due to alkoxy groups: the highest electron density moving from the 1,3-dithiole moiety toward the central thiophene ring.

  DOI：

  10.1021/jo981312b
• 作为产物：
  描述：

  3,4-bis(hexyloxy)-2-thiophene 在 正丁基锂 、 四甲基乙二胺 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.5h， 生成 3,4-dihexyloxythiophene-2,5-dicarbaldehyde
  参考文献：
  名称：

  Low Oxidation Potential Tetrathiafulvalene Analogues Based on 3,4-Dialkoxythiophene π-Conjugating Spacers

  摘要：

  Tetrathiafulvalene analogues involving dihexyloxythiophene (1), ethylenedioxythiophene (2), and bis(3,4-dihexyloxy-2-thienyl)ethylene (3) as conjugating spacer and diversely substituted at the 1,3-dithiole ring (R) have been synthesized. Electronic absorption spectra show the expected decrease of HOMO-LUMO gap when increasing the electron-releasing power of R or the length of the conjugating spacer. Cyclic voltammetry (CV) shows that whereas compounds 1 and 2 are reversibly oxidized into their cation radical and dication through two one-electron steps, for compounds 3 the dication is formed directly via a two-electron transfer. Comparison of the data for compounds 2 and 3 with those of their respective analogues based on thiophene and dithienylethylene shows that introduction of the electron-donating alkoxy groups at the 3 and 4 positions of the thiophene ring produces a 150-200 mV negative shift of the first redox potential (E degrees(1)). On the other hand, CV data for compounds 1 and 2 reveal several unusual features such as E degrees(1) approximate to 0.10 V/SCE ranking among-the lowest known to date and a Coulombic repulsion between positive charges in the dication larger than for the analogue ct-donors based on unsubstituted thiophene. These results are interpreted by a major reorganization of the electronic distribution in the donor molecule due to alkoxy groups: the highest electron density moving from the 1,3-dithiole moiety toward the central thiophene ring.

  DOI：

  10.1021/jo981312b

文献信息

• Nouveaux systèmes conjugués à états redox multiples
  作者：J.-M. Raimundo、S. Akoudad、H. Brisset、J. Roncali

  DOI：10.1051/jcp:1998254

  日期：1998.6

  De nouveaux systèmes conjugués linéaires basés sur l'association de donneurs thiophéniques et du tétracyanoindane préparé à partir de l'indan-1,3-dione ont été synthétisés. Les données optiques et électrochimiques révèlent un fort pouvoir accepteur d'électrons ainsi qu'un faible écart HOMO-LUMO.

  我们合成了新的线性共轭体系，该体系基于噻吩给体与由茚满-1,3-二酮制备的四氰基茚满的结合。光学和电化学数据显示，该系统具有较高的电子受体容量和较低的 HOMO-LUMO 间隙。