(E)-2,2’,6,6’-tetrafluoro-4,4’-diiodoazobenzene | 1415919-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2,2’,6,6’-tetrafluoro-4,4’-diiodoazobenzene
• 英文别名: (E)-2,2',6,6-tetrafluoro-4,4'-diiodoazobenzene；(E)-1,2-bis(2,6-difluoro-4-iodophenyl)diazene
• CAS: 1415919-96-8
• 化学式: C₁₂H₄F₄I₂N₂
• 分子量: 505.98
• InChiKey: ZQCGCBYJIVHGRR-FMQUCBEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.72
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-2,2’,6,6’-tetrafluoro-4,4’-diiodoazobenzene 以 乙腈 为溶剂， 反应 0.33h， 生成 (Z)-2,2',6,6'-tetrafluoro-4,4'-diiodoazobenzene
  参考文献：
  名称：

  氟化偶氮苯作为超分子卤素键的构建基块

  摘要：

  邻-氟偶氮苯是双稳态光开关的一个显着实例，可通过可见光寻址。对称的，高度氟化的偶氮苯在对位上带有碘取代基与中性卤素键合受体如二甲基吡啶组合，在溶液中和在固态下均显示-位是合适的超分子结构单元。因此，我们研究了一系列偶氮苯光开关的光化学。引入碘乙炔基后，溶液中的卤素键合给体性能显着增强。但是，π→π*波段的红移导致与n→π*波段的部分重叠，从而使其难于处理。碘取代基的引入还伴随着缩短的热半衰期。通过改变DFT的计算合理地讨论了一系列具有不同卤素键合给体性质的三种偶氮苯与它们不断变化的光物理性质之间的关系。

  DOI：

  10.3762/bjoc.15.197
• 作为产物：
  描述：

  2,6-二氟-4-碘苯胺 在 ferrous(II) sulfate heptahydrate 、 potassium permanganate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以10%的产率得到(E)-2,2’,6,6’-tetrafluoro-4,4’-diiodoazobenzene
  参考文献：
  名称：

  邻氟偶氮苯作为易于合成的光开关，可在可见光下提供近乎定量的双向异构化

  摘要：

  用邻氟原子官能化的偶氮苯具有较低的 Z 异构体 n 轨道能量，导致 E 和 Z 异构体的 n→π* 吸收带分离。引入对位取代基可以进一步调整邻氟偶氮苯的吸收光谱。特别是，吸电子酯基会导致 n→π* 跃迁的间隔为 50 nm。因此，绿光和蓝光可分别用于诱导 E→Z 和 Z→E 异构化。邻氟偶氮苯支架很容易合成，并且可以通过其芳基末端插入更大的结构中。这些新的偶氮苯衍生物可以通过两种方式进行转换，具有高光转化率，并且它们的 Z 异构体显示出非常长的热半衰期。

  DOI：

  10.1021/ja310323y

文献信息

• Active Ester Functionalized Azobenzenes as Versatile Building Blocks
  作者：Sven Schultzke、Melanie Walther、Anne Staubitz

  DOI：10.3390/molecules26133916

  日期：——

  conditions for the introduction of NHS esters to azobenzenes and diazocines has been established. Yields were consistently high with very few exceptions. The NHS functionalized azobenzenes react with primary amines quantitatively. These amines are ubiquitous in biological systems and in material science.

  偶氮苯是重要的分子开关，但仍然难以选择性地官能化。已经建立了一种在温和条件下将 NHS 酯引入偶氮苯和重氮辛的高产率 Pd 催化交叉偶联方法。除了极少数例外，产量一直很高。NHS 官能化偶氮苯与伯胺定量反应。这些胺在生物系统和材料科学中无处不在。
• COMPOSITION AND METHOD FOR MANUFACTURING RESINS
  申请人：Cambium Biomaterials, Inc.

  公开号：US20210130310A1

  公开（公告）日：2021-05-06

  Certain embodiments of the invention described herein comprise a composition of matter, and method for preparing the same, which provide the benefits of pre-reaction molecular configuration favoring high liquidity properties, and post-reaction configuration that favors mechanical strength, stiffness, and properties associated with high viscous and/or solid-state materials. In some embodiments, the composition of matter can comprise relaxing photo-isomerizable fragments, of which a fraction can be transformed from trans to cis configurations upon exposure to a photon source. In some embodiments, the composition of matter further comprises thermally reactive fragments, of which can enable thermal solidification of a mixture upon exposure to elevated temperatures. In some embodiments, a composition of matter can be combined with reinforcing additives to form a prepreg combination.

  本发明的某些实施例包括一种物质组成和制备方法，其提供了预反应分子构型有利于高液性能的好处，以及后反应构型有利于机械强度、刚度和与高粘性和/或固态材料相关的性能。在某些实施例中，该物质组成可以包括放松的光异构化片段，其中一部分在暴露于光子源时可以从顺式构型转变为顺式构型。在某些实施例中，该物质组成进一步包括热反应片段，其中可以使混合物在暴露于高温时热固化。在某些实施例中，物质组成可以与增强添加剂结合形成预浸涂组合。
• Sulfur and Azobenzenes, a Profitable Liaison: Straightforward Synthesis of Photoswitchable Thioglycosides with Tunable Properties
  作者：Jonathan Berry、Thisbe K. Lindhorst、Guillaume Despras

  DOI：10.1002/chem.202200354

  日期：2022.7.11

  Tunable properties: A direct thioarylation of azobenzenes allows to obtain symmetrical as well as challenging unsymmetrical conjugates in good yields. Importantly, photochromic and thermal relaxation properties can be easily tuned via oxidation of the sulfide linkage.

  可调特性：偶氮苯的直接硫代芳基化可以以良好的产率获得对称以及具有挑战性的不对称缀合物。重要的是，光致变色和热弛豫特性可以通过硫键的氧化轻松调节。
• COMPOSITION AND METHOD FOR MANUFACTURING CURED RESINS
  申请人：Cambium Biomaterials, Inc.

  公开号：US20210130534A1

  公开（公告）日：2021-05-06

  Certain embodiments of the invention described herein comprise a composition of matter, and method for preparing the same, which provide the benefits of pre-reaction molecular configuration favoring high liquidity properties, and post-reaction configuration that favors mechanical strength, stiffness, and properties associated with high viscous and/or solid-state materials. In some embodiments, the composition of matter can comprise relaxing photo-isomerizable fragments, of which a fraction can be transformed from trans to cis configurations upon exposure to a photon source. In some embodiments, the composition of matter further comprises thermally reactive fragments, of which can enable thermal solidification of a mixture upon exposure to elevated temperatures. In some embodiments, a composition of matter can be combined with reinforcing additives to form a prepreg combination.
• COMPOSITION AND METHOD FOR MANUFACTURING PREPREG COMPOSITIONS
  申请人：Cambium Biomaterials, Inc.

  公开号：US20210130579A1

  公开（公告）日：2021-05-06

  Certain embodiments of the invention described herein comprise a composition of matter, and method for preparing the same, which provide the benefits of pre-reaction molecular configuration favoring high liquidity properties, and post-reaction configuration that favors mechanical strength, stiffness, and properties associated with high viscous and/or solid-state materials. In some embodiments, the composition of matter can comprise relaxing photo-isomerizable fragments, of which a fraction can be transformed from trans to cis configurations upon exposure to a photon source. In some embodiments, the composition of matter further comprises thermally reactive fragments, of which can enable thermal solidification of a mixture upon exposure to elevated temperatures. In some embodiments, a composition of matter can be combined with reinforcing additives to form a prepreg combination.