4-(6-aminohexyloxy)azobenzene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4-(6-aminohexyloxy)azobenzene
• 英文别名: 6-(4-Phenyldiazenylphenoxy)hexan-1-amine；6-(4-phenyldiazenylphenoxy)hexan-1-amine
• 化学式: C₁₈H₂₃N₃O
• 分子量: 297.4
• InChiKey: NUWDDVOYTZCVGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(6-aminohexyloxy)azobenzene 在 氢溴酸 作用下， 以 乙醚 为溶剂， 以36.6%的产率得到
  参考文献：
  名称：

  Preparation and optical characteristics of layered perovskite-type lead-bromide-incorporated azobenzene chromophores

  摘要：

  Lead bromide-based layered perovskite powders with azobenzene derivatives were prepared by a homogeneous precipitation method. From the diffuse reflectance (DR) and photoluminescence (PL) spectra of the hybrid powder materials, the present hybrids exhibited sharp absorption and PL peaks originating from excitons produced in the PbBr42- layer. When the present hybrid powder was irradiated with UV light at 350 nm, the absorption band from the trans-azobenzene chromophore, observed around 350 nm, decreased, while the absorption band from the cis-azobenzene chromophore, observed around 450 nm, increased. These results indicate that azobenzene chromophores in the present hybrid materials exhibit reversible photoisomerization. Moreover, it was found that the PL intensity from the exciton also varied due to photoisomerization of the azobenzene chromophores in the present hybrid. Thus, for the first time we succeeded in preparing the azobenzene derivative lead-bromide-based layered perovskite with photochromism before and after UV light irradiation. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jssc.2012.11.009
• 作为产物：
  描述：

  4-N-苯基苯酰胺 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 11.0h， 生成 4-(6-aminohexyloxy)azobenzene
  参考文献：
  名称：

  Photoresponsive Crown Ethers. 19. Photocontrol of Reversible Association-Dissociation Phenomena in “Tail(Ammonium)-Biting” Crown Ethers

  摘要：

  通过测量平均分子量和电导率，评估了具有冠环和连接在偶氮苯两侧的氨烷基（H3N+-(CH2)n-，n=4、6、10）的光致发光冠醚（1）的聚集特性。平均分子量的渗透测定结果表明，所有反式异构体（反式-1（n=4、6、10））都因分子间冠铵络合而形成了伪环二聚体。光异构化的顺式-1（n=6）和顺式-1（n=10）在光异构化时，铵基与冠发生分子内 "咬合"，从而以离散单体的形式存在。另一方面，顺式-1（n=4）由于含有短的四亚甲基间隔，不能形成分子内 "咬尾 "复合物，而是以假环二聚体的形式存在。电导率很好地反映了这种差异：在 1（n=6）和 1（n=10）中，电导率随反式到顺式的光异构化同步增加，随顺式到反式的光异构化同步减少。而在 1（n=4）中几乎检测不到这种光致电导变化。此外，强制二聚物解离为单体的添加剂抑制了光诱导电导变化的幅度。这是光能传递到电导变化的一个新例子。

  DOI：

  10.1246/bcsj.60.1819

文献信息

• Photoresponsive Crown Ethers. 19. Photocontrol of Reversible Association-Dissociation Phenomena in “Tail(Ammonium)-Biting” Crown Ethers
  作者：Seiji Shinkai、Tohru Yoshida、Kiminori Miyazaki、Osamu Manabe

  DOI：10.1246/bcsj.60.1819

  日期：1987.5

  The aggregation properties of photoresponsive crown ethers (1) having a crown ring and an ammonioalkyl (H3N+–(CH2)n−, n=4, 6, 10) group attached to the two sides of an azobenzene have been evaluated through the measurements of average molecular weights and electric conductance. Osmometric determination of average molecular weights established that all trans-isomers (trans-1 (n=4, 6, 10)) form the pseudocyclic dimers due to intermolecular crown-ammonium complexation. Photoisomerized cis-1 (n=6) and cis-1 (n=10), which have been designed so that intramolecular “biting” of the ammonio group to the crown can occur upon photoisomerization, existed as the discrete monomers. On the other hand, cis-1 (n=4), which cannot form the intramolecular “tail-biting” complex because of the short tetramethylene spacer, existed as the pseudo-cyclic dimer. This difference was well reflected by electric conductance: in 1 (n=6) and 1 (n=10), the conductance increased synchronously with trans-to-cis photoisomerization and decreased with cis-to-trans photoisomerization. Such a photoresponsive conductance change was scarcely detected for 1 (n=4). Furthermore, the additives which enforce dissociation of the dimeric species to the monomeric species suppressed the magnitude of the photoinduced conductance change. This is a novel example that the light energy is transmitted to the conductance change.

  通过测量平均分子量和电导率，评估了具有冠环和连接在偶氮苯两侧的氨烷基（H3N+-(CH2)n-，n=4、6、10）的光致发光冠醚（1）的聚集特性。平均分子量的渗透测定结果表明，所有反式异构体（反式-1（n=4、6、10））都因分子间冠铵络合而形成了伪环二聚体。光异构化的顺式-1（n=6）和顺式-1（n=10）在光异构化时，铵基与冠发生分子内 "咬合"，从而以离散单体的形式存在。另一方面，顺式-1（n=4）由于含有短的四亚甲基间隔，不能形成分子内 "咬尾 "复合物，而是以假环二聚体的形式存在。电导率很好地反映了这种差异：在 1（n=6）和 1（n=10）中，电导率随反式到顺式的光异构化同步增加，随顺式到反式的光异构化同步减少。而在 1（n=4）中几乎检测不到这种光致电导变化。此外，强制二聚物解离为单体的添加剂抑制了光诱导电导变化的幅度。这是光能传递到电导变化的一个新例子。
• Intercalation and Photochemical Behavior of Azobenzene Derivatives with Layered Polymer Crystals as the Organic Host
  作者：Shinya Oshita、Akikazu Matsumoto

  DOI：10.1246/cl.2003.712

  日期：2003.8

  A photofunctional organic solid was fabricated by the intercalation of azobenzene derivatives containing an amino group into poly(muconic acid) as the layered polymer crystals. The organic intercalation and photoisomerization behaviors depended on the structure of the spacer between the azobenzene and amino groups of the guest.

  通过将含有氨基的偶氮苯衍生物插层到层状聚合物晶体聚（粘多酸）中，制备了一种光功能有机固体。有机插层和光异构化行为取决于客体的偶氮苯和氨基之间的间隔物结构。
• 一种用于氧化锌纳米粒子稳定配体的偶氮类小分子的合成方法
  申请人：宁波大学

  公开号：CN114773222A

  公开（公告）日：2022-07-22

  本发明公开了一种用于氧化锌纳米粒子稳定配体的偶氮类小分子的合成方法。采用两步法合成目标分子AZO‑NH2，其中第一步用4‑苯偶氮基苯酚和N‑(6‑溴己基)邻苯二甲酰亚胺等试剂为原料合成一种白色中间体，第二步再在第一步所得到的中间体中加入水合肼等试剂经过萃取、干燥、柱层析等一系列步骤最终得到AZO‑NH2。实验过程中所使用的试剂均为无毒试剂，能确保实验过程的安全。
• Preparation and optical characteristics of layered perovskite-type lead-bromide-incorporated azobenzene chromophores
  作者：Ryo Sasai、Hisashi Shinomura

  DOI：10.1016/j.jssc.2012.11.009

  日期：2013.2

  Lead bromide-based layered perovskite powders with azobenzene derivatives were prepared by a homogeneous precipitation method. From the diffuse reflectance (DR) and photoluminescence (PL) spectra of the hybrid powder materials, the present hybrids exhibited sharp absorption and PL peaks originating from excitons produced in the PbBr42- layer. When the present hybrid powder was irradiated with UV light at 350 nm, the absorption band from the trans-azobenzene chromophore, observed around 350 nm, decreased, while the absorption band from the cis-azobenzene chromophore, observed around 450 nm, increased. These results indicate that azobenzene chromophores in the present hybrid materials exhibit reversible photoisomerization. Moreover, it was found that the PL intensity from the exciton also varied due to photoisomerization of the azobenzene chromophores in the present hybrid. Thus, for the first time we succeeded in preparing the azobenzene derivative lead-bromide-based layered perovskite with photochromism before and after UV light irradiation. (c) 2012 Elsevier Inc. All rights reserved.