5-{2,5-bis(2-ethylhexyloxy)-4-[4-(diethylamino)styryl]styryl}thiophene-2-carbaldehyde | 958007-19-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 5-{2,5-bis(2-ethylhexyloxy)-4-[4-(diethylamino)styryl]styryl}thiophene-2-carbaldehyde
• CAS: 958007-19-7
• 化学式: C₄₁H₅₇NO₃S
• 分子量: 643.974
• InChiKey: QDZFOJYSYFBRGV-ULAJWHHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.94
• 重原子数：
  46.0
• 可旋转键数：
  22.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-{2,5-bis(2-ethylhexyloxy)-4-[4-(diethylamino)styryl]styryl}thiophene-2-carbaldehyde 、 2-(3-氰基-4,5,5-三甲基呋喃-2(5H)-亚甲基)丙二腈 在 哌啶 作用下， 以 四氢呋喃 为溶剂， 以39%的产率得到4-((1E)-2-(5-(2,5-bis(2-ethylhexyloxy)-4-(4-(diethylamino)styryl)styryl)thiophen-2-yl)vinyl)-2-(dicyanomethylene)-2,5-dihydro-5,5-dimethylfuran-3-carbonitrile
  参考文献：
  名称：

  Push-Pull Chromophore with Phenylene and Thiophene as Conjugation Bridge for Electro-Optic Applications

  摘要：

  We designed and synthesized a push-pull type chromophore (PT-TCF) containing phenylene and thiophene ring as a conjugation bridge. Bulky alkyl chain was substituted into the phenylene bridge to minimize the intermolecular interaction among the neighbor molecules and to enhance solubility of the chromophore in solvents and a polymer host. H-1 NMR and (H-1H)-H-1 COSY spectroscopy confirmed that the chromophore was in all trans-ethenyl conformation. The chromophore exhibited fairly high melting point of 188 degrees C. The chromophore was thermally stable up to 220 degrees C in the nitrogen atmosphere. The relatively high melting point and decomposition on-set may be attributable to the rigid bridge component. The chromophore was blended with an optically transparent polymer host to make a thin film and then its macroscopic optical nonlinearities were evaluated. In a preliminary result, the polymer films containing PT-TCF as a concentration of 50 wt% exhibited electro-optic coefficient as large as 22pm/V taken at 1.55 mu m.

  DOI：

  10.1080/15421400601021505
• 作为产物：
  描述：

  diethyl [[2,5-bis(2-ethylhexyloxy)-4-bromophenyl]methyl]phosphonate 在 正丁基锂 、 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 正庚烷 、 乙基苯 为溶剂， 反应 35.0h， 生成 5-{2,5-bis(2-ethylhexyloxy)-4-[4-(diethylamino)styryl]styryl}thiophene-2-carbaldehyde
  参考文献：
  名称：

  Push-Pull Chromophore with Phenylene and Thiophene as Conjugation Bridge for Electro-Optic Applications

  摘要：

  We designed and synthesized a push-pull type chromophore (PT-TCF) containing phenylene and thiophene ring as a conjugation bridge. Bulky alkyl chain was substituted into the phenylene bridge to minimize the intermolecular interaction among the neighbor molecules and to enhance solubility of the chromophore in solvents and a polymer host. H-1 NMR and (H-1H)-H-1 COSY spectroscopy confirmed that the chromophore was in all trans-ethenyl conformation. The chromophore exhibited fairly high melting point of 188 degrees C. The chromophore was thermally stable up to 220 degrees C in the nitrogen atmosphere. The relatively high melting point and decomposition on-set may be attributable to the rigid bridge component. The chromophore was blended with an optically transparent polymer host to make a thin film and then its macroscopic optical nonlinearities were evaluated. In a preliminary result, the polymer films containing PT-TCF as a concentration of 50 wt% exhibited electro-optic coefficient as large as 22pm/V taken at 1.55 mu m.

  DOI：

  10.1080/15421400601021505