4-hydroxy-4′-n-decyloxyazobenzene | 197570-96-0

• 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-hydroxy-4′-n-decyloxyazobenzene
• 英文别名: 4-decyl-4'-hydroxyazobenzene；4-(4-Decyloxyphenylazo)phenol；4-[(4-decoxyphenyl)diazenyl]phenol
• CAS: 197570-96-0
• 化学式: C₂₂H₃₀N₂O₂
• 分子量: 354.492
• InChiKey: RTBATSPABCITAY-UHFFFAOYSA-N

物化性质

• 沸点：
  510.1±30.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  54.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-4′-n-decyloxyazobenzene 在 氢氧化钾 作用下， 以 乙醇 、 苯 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Orientation and Spectral Characteristics of the Azobenzene Chromophore in the Ammonium Bilayer Assembly

  摘要：

  AbstractAzobenzene‐containing, single‐chain ammonium amphiphiles in which the alkyl chain length in the tail and spacer portions was systematically varied were prepared, and their aggregation behavior in water was studied by electron microscopy, differential scanning calorimetry and absorption spectroscopy. These amphiphiles exist as molecular dispersions, hydrated microcrystals, micelles, or bilayers. The formation of stable bilayers was deduced on the basis of three criteria which include the spectral agreement between aqueous dispersions and the corresponding cast films. Stable bilayers were obtainable when the sum of tail and spacer is not smaller than C14 to C16, and the tail is at least C8. Double‐chain ammonium amphiphiles which possess an octadecyl chain in addition to the azobenzene‐containing chain were prepared and shown to form stable bilayers. The absorption spectrum reflected the aggregate structure. In particular, the bilayer spectra were classified into four types: type A (λmax ca. 300 nm) for the parallel chromophore orientation (H aggregate), type B (330 – 340 nm) for the dimeric chromophore, type C (ca. 355 nm) for the isolated chromophore, and type D (360–390 nm) for the head‐to‐tail chromophore orientation (J‐like aggregate). Liquid‐crystalline bilayers gave type B spectra, while crystalline bilayers gave either of types A, B, and D, depending on the alkyl chain length. Finally, various examples of spectral control were discussed in relation to the present results.

  DOI：

  10.1002/bbpc.19830871211
• 作为产物：
  描述：

  4-癸烷氧基苯胺 在 盐酸 、 sodium hydroxide 、 sodium nitrate 作用下， 以 水 为溶剂， 生成 4-hydroxy-4′-n-decyloxyazobenzene
  参考文献：
  名称：

  Side-Chain Liquid-Crystalline Polyoxetanes with a Spacer-Separated Azobenzene Moiety. II. Preparation and Characterization of Polyoxetanes Derived from 4-(4-Alkoxyphenylazo)phenyl 4-[7-(3-Methyl-3-oxetanyl)-1,6-dioxaheptyl]benzoates

  摘要：

  在 20 至 30 °C 的二氯甲烷中，使用 0.08 摩尔量的 THF-BF3，通过阳离子开环聚合 4-(4-烷氧基苯基偶氮)苯基 4-[7-(3-甲基-3-氧杂环丁基)-1,6-二氧杂庚基]苯甲酸酯，制备了一系列聚氧杂环丁烷。尽管产品聚合物的 GPC 平均分子量约为 9000 到 23000，但在大多数情况下，它们并不具有单峰分子量分散性。聚合物的液晶介相通过差示扫描量热法和偏振光学显微镜进行了检测；在从约 250 °C 到室温的较宽温度范围内，均可观察到由于向列型和/或胶粘型介相而产生的纹理。苯甲酸酯分子、较长的对取代烷氧基尾端和氧杂环丁烷主链在维持高度有序、稳定的介相方面发挥了重要作用。

  DOI：

  10.1246/bcsj.70.175

文献信息

• Phototunable Liquid-Crystalline Phases Made of Nanoparticles
  作者：Anna Zep、Michal M. Wojcik、Wiktor Lewandowski、Kaja Sitkowska、Aleksander Prominski、Jozef Mieczkowski、Damian Pociecha、Ewa Gorecka

  DOI：10.1002/anie.201407497

  日期：2014.12.8

  distance between metal sublayers in the lamellar phase. Interestingly, the azo derivatives attached to the nanoparticle surface show very different kinetics of cis/trans conformational change as compared to the free molecules. The cis form of free ligands in solution is stable for days, whereas the isomerization of molecules attached to the nanoparticle surface to the trans form takes only a few minutes

  介绍了由接枝有光敏偶氮化合物的无机纳米粒子制成的液晶（LC）杂化系统的性能。对于表面上具有大量偶氮配体的材料，LC结构可以被紫外线可逆地熔化，并且返回LC状态不需要吸收可见光。对于偶氮配体密度较低的系统，紫外线会缩短层状相中金属亚层之间的距离。有趣的是，与游离分子相比，附着于纳米颗粒表面的偶氮衍生物显示出非常不同的顺/反构象变化动力学。该顺溶液中游离配体的形式稳定数天，而附着在纳米颗粒表面的分子异构化为反式仅需几分钟。显然，由于拥挤的环境，固定在金属表面的偶氮配体的行为与它们在缩合状态下的行为相同。
• 一种液晶半导体材料及其制备方法和应用
  申请人：北京大学深圳研究生院

  公开号：CN108238973A

  公开（公告）日：2018-07-03

  本发明公开一种液晶半导体材料及其制备方法和应用。该液晶半导体材料包括有机半导体母核基团、光致变色基团和热致液晶基团，有机半导体母核是整个分子的核心部分，光致变色基团对紫外光和可见光敏感的性质可进行构象或结构上的转变，热致液晶基团赋予分子液晶相的特性从而利用其优越的液晶性质使分子排列更有序，进而实现热致半导体材料并且提高迁移率。采用蒸镀手段将本发明液晶半导体材料制备有机薄膜晶体管，在照射紫外光后器件性能有明显的提升，在紫外光和退火双重作用下器件的性能更是再度提升。此种功能型的半导体材料将实现它们特有的潜质，应用在光电器件中例如智能器件、传感器和功能性开关等等。
• Preparation and Characterization of Side-Chain Liquid-Crystalline Polyoxetanes Anchoring a Pendant Spacer-Separated Mesogen at the Tertiary-Like C-3 Carbon of the Oxetane Unit
  作者：Hiroshi Ogawa、Yasutake Kodera、Shigeyoshi Kanoh、Akihiko Ueyama、Masatoshi Motoi

  DOI：10.1246/bcsj.71.433

  日期：1998.2

  Polyoxetanes anchoring a pendant spacer-separated mesogen at the tertiary-like C-3 carbon of the oxetane unit were prepared by cationic ring-opening polymerization of the corresponding oxetane derivatives. The resulting polymers were liquid-crystalline substances showing textures assignable to the nematic or smectic mesophase over a wide temperature range from about 260 °C to room temperature. These mesogens also behaved in the manner similar to that of the mesogens in the analogous polyoxetanes attached by a methyl side chain at the quaternary C-3 carbon, although the less bulky polymer backbone in the present work indicated a somewhat higher isotropic phase-transition temperature than that of the methyl-substituted analogs. In both types of the polyoxetanes, their mesophase patterns were influenced by the core structure and alkoxy tail length in the pendant mesogen, but not by the bulkiness of the second side chains, H and CH3, attached at the C-3 carbon of the polyoxetane unit.

  通过阳离子开环聚合相应的氧杂环丁烷衍生物，制备了在氧杂环丁烷单元的叔碳C-3上锚定由间隔的悬浮剂分离的中介物的聚氧杂环丁烷。所得聚合物是液晶物质，在约260℃到室温的宽温度范围内，其纹理可归因于向列或层状中相。这些中介物也表现出与在季碳C-3上通过甲基侧链连接的类似聚氧杂环丁烷中的中介物相似的行为，尽管本研究中不太笨重的聚合物骨架表明其各向同性相变温度比甲基取代的类似物高一些。在这两种类型的聚氧杂环丁烷中，其中相模式受核心结构和悬垂中介物中的烷氧基尾长的影响，但不受在聚氧杂环丁烷单元的C-3上连接的第二个侧链H和CH3的笨重程度的影响。
• Mesogenic cyclopentadienyl cyclopalladated azobenzene complexes
  作者：Mauro Ghedini、Daniela Pucci、Francesco Neve

  DOI：10.1039/cc9960000137

  日期：——

  The novel coordinatively saturated cyclopentadienyl palladium complexes [PdLn(η5-C5H5)](HLn= thermotropic 4-R,4′-R′-azobenzene; n= 1, R = R′= C6H13; n= 2, R = R′= C6H13O; n= 3, R = C6H13O, R′= C8H17OC6H4CO2; n= 4, R = C10H21O, R′= C8H17OC6H4CO2) are dark red solids which melt into isotropic fluids for n= 1,2, whereas for n= 3,4 liquid crystalline properties are exhibited with a stabilization of melting and clearing temperatures as high as 70 °C.

  新型配位饱和环戊二烯钯配合物[PdLn(η5-C5H5)]（HLn=热致性4-R,4′-R′-偶氮苯；n=1，R=R′=C6H13；n=2，R=R′= O；n=3，R= O，R′=C8H17OC6H4CO2；n= 4，R = C10H21O，R′= C8H17OC6H4CO2）是暗红色固体，在 n= 1、2 时熔化成各向同性的流体，而在 n= 3、4 时则表现出液晶特性，熔化和清除温度稳定，高达 70 °C。
• Room-temperature organometallic chiral liquid crystals: azoxymercury complexes
  作者：Ana Omenat、Mauro Ghedini

  DOI：10.1039/c39940001309

  日期：——

  The new mercury complexes [HgL nCl][HL = 4-(n-CnH2n+ 1)-4′-S-(+)-2-octyloxy} azobenzene, n= 6,10] are liquid crystals which exhibit a chiral smectic C* mesophase at room temperature and clear at about 60 °C.

  新型汞配合物 [HgL nCl][HL = 4-(n-CnH2n+ 1)-4′-S-(+)-2-辛氧基}偶氮苯，n= 6,10] 是具有手性近晶相的液晶C* 室温下为中间相，约 60 °C 时为透明。