diethyl [[2,5-bis(2-ethylhexyloxy)-4-bromophenyl]methyl]phosphonate | 357396-90-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl [[2,5-bis(2-ethylhexyloxy)-4-bromophenyl]methyl]phosphonate
• 英文别名: diethyl[2,5-bis(2-ethylhexyloxy)-4-bromo-benzyl]phosphonate
• CAS: 357396-90-8
• 化学式: C₂₇H₄₈BrO₅P
• 分子量: 563.553
• InChiKey: CNNHEOLSMCOQBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.41
• 重原子数：
  34.0
• 可旋转键数：
  20.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-ethylhexyl 4-methylbenzenesulfonate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 四丁基氯化铵 、 potassium carbonate 作用下， 以 四氯化碳 、 丁酮 为溶剂， 反应 19.5h， 生成 diethyl [[2,5-bis(2-ethylhexyloxy)-4-bromophenyl]methyl]phosphonate
  参考文献：
  名称：

  具有富勒烯侧链的共轭聚合物的光致电子转移和光伏器件。

  摘要：

  DOI：

  10.1021/ja015614y

文献信息

• Supramolecular Ladder Assemblies as a Model for Probing Electronic Interactions between Multiple Stacked π‐Conjugated Systems
  作者：Chi‐Huao Huang、Damien Jardel、Guillaume Lautrette、Isabelle Pianet、Alexander Kuhn、Dario M. Bassani

  DOI：10.1002/cphc.202000857

  日期：2021.1.18

  is used to induce the supramolecular assembly of n×m ladders containing 1, 2, or 3 triphenylenevinylene units appended with BA. The topological constraint enforced by the architectures induces through‐space interactions between the electroactive moieties that are reflected in the electronic absorption and emission spectrum. The n=2, m=2 or m=3 architectures undergo two single electron oxidation events

  一系列单，双和三位受体，其中融合了与巴比妥酸（BA）互补的H键位，可诱导n × m梯形的超分子组装，其中梯形包含1、2或3个带有BA的三亚苯基亚乙烯基单元。该体系结构强制执行的拓扑约束条件导致电子吸收和发射光谱中反映的电活性部分之间的空间相互作用。所述Ñ = 2，米= 2或米= 3结构经历了两次单电子氧化事件，这表明相应的单和双自由基阳离子物种的形成，其复合比例常数分别为340和70。电化学势的比较表明，电荷在组件中的电活性单元上被分散了。
• Thermally Stable Nonlinear Optical Polymers Based on Polyimides Substituted with Chromophores Containing Julolidine Moiety
  作者：Hyun Kyung Ju、Jong Sun Lim、Changjin Lee、Dong Hoon Choi、Dong Wook Kim

  DOI：10.1080/15421400802329590

  日期：2008.9.30

  We designed and synthesized a NLO chromophore adopting the concept of shape modification as well as possessing high thermal stability. The chromophore was featured by a phenylene ring as a conjugation bridge, a bulky alkyl chain attached on the side of the conjugation bridge, and julolidine moiety as an electron donor. The NLO chromophore was attached to the polyimide as a side chain, resulting in thermally durable NLO polymers. On set decomposition temperature of the NLO chromophore was measured 330 degrees C in TGA analysis. The NLO polymer exhibited high glass transition temperature of 150 degrees C and was thermally stable up to 250 degrees C. The polymer was quite soluble in common solvents and produced an optical quality film by spin-coating. The electro-optic coefficient of the film was measured using 1.55 mu m laser source, giving as high as 30 pm/V at the poling condition of 150 degrees C and 1 MV/cm.