4-(4-Pentyloxy-phenylazo)-benzoic acid | 136954-79-5

• 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-(4-Pentyloxy-phenylazo)-benzoic acid
• CAS: 136954-79-5
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: DKXFKIBLLRRYGF-FMQUCBEESA-N

物化性质

• 沸点：
  494.2±25.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  71.25
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  胆固醇 、 4-(4-Pentyloxy-phenylazo)-benzoic acid 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以42%的产率得到4-n-pentoxy-4'-((cholesteryloxy)carbonyl)azobenzene
  参考文献：
  名称：

  Thermal and Light Control of the Sol-Gel Phase Transition in Cholesterol-Based Organic Gels. Novel Helical Aggregation Modes As Detected by Circular Dichroism and Electron Microscopic Observation

  摘要：

  Nineteen cholesterol derivatives containing a variety of azobenzene moieties coupled to C-3 of a steroidal moiety through an ester linkage were synthesized. We employed two different esterification methods by which cholesterol derivatives with the natural (S)-configuration at C-3 and those with the inverted (R)-configuration at C-3 were obtained (the latter derivatives are indicated by a prime). Among them, cholesterol derivatives bearing a p-alkoxyazobenzene moiety (2R and 2R') acted as excellent thermally-reversible gelators of various organic fluids, but the gelation ability is fairly different between 2R and 2R': 2R could gelatinize hydrocarbons such as n-hexane, n-octane, and toluene, halogen solvents such as 1,2-dichloroethane and dichloromethane, ether solvents such as diethyl ether and THF, and alcohols such as ethanol and I-butanol whereas 2R' could gelatinize ketones, methanol, and polysiloxanes. In general, the solubility of 2R' in apolar solvents is superior to that of 2R, so 2R is useful for gelation of apolar solvents whereas 2R' is useful for gelation of polar solvents. We found that the sol-gel phase transition is sensitively ''read-out'' by a change in the circular dichroism (CD) spectrum: the gel phase is CD-active whereas the sol phase is totally CD-silent. For example, the 2Me-1-butanol gel gave a positive exciton coupling band with (R)-chirality whereas the 2Et'-methanol gel gave a negative exciton coupling band with (S)-chirality. These results mean that dipoles in the azobenzene moiety are oriented in a clockwise (in (R)-chirality) or anticlockwise (in (S)-chirality) direction when they interact in the excited state. Strangely, we accidentally found that the CD sign of the gels prepared from 2Pr, 2Bu, and 3Me' (azobenzene-linked cholesterol derivative with p-NMe(2)) is frequently inverted. After careful examination of the gel preparation conditions, we found that inversion takes place only when the cooling speed is fast. The scanning electron microscopic studies established that gelators form three-dimensional networks with helical fibrils. Interestingly, we found that in the 3Me' gel prepared from cyclohexane the gel with (R)-chirality in CD possesses a right- handed helix whereas the gel with (S)-chirality in the CD possesses a left-handed helix. The sol-gel phase transition was also induced by photoresponsive cis-trans isomerism of the azobenzene moiety: the gel formed from the trans-isomer was efficiently converted to the sol when trans-to-cis isomerization was photochemically induced, and this process can be repeated reversibly. The photoinduced sol-gel phase transition was also ''read-out'' as a change in CD spectroscopy.

  DOI：

  10.1021/ja00094a023
• 作为产物：
  描述：

  ethyl (E)-4-((4-(pentyloxy)phenyl)diazenyl)benzoate 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 4-(4-Pentyloxy-phenylazo)-benzoic acid
  参考文献：
  名称：

  Monotropic or enantiotropic mesophases? Liquid-crystalline and solid state polymorphism 4-Chloro-1,3-phenylene bis-[4-(4-alkyloxyphenylazo)benzoates

  摘要：

  This article presents a homologous series of bent-core molecules consisting of a 4-chlororesorcinol as a central unit and 4-[(4-alkyloxyphenyl)diazenyl]benzoic acids as wings. With the use of polarizing optical microscopy (POM), thermal analysis (TOA) and differential scanning calorimetry (DSC) the mesogenic properties were detected. Furthermore, the X-ray diffraction (XRD) measurements were also performed for selected samples. Compounds of the above mentioned series form nematic, B-6, and smectic C mesophases. An interesting phenomenon in the solid phase polymorphism was observed in some cases. In our experiment one crystalline form (CrI) melts to nematic phase while the second form (CrII)melts at higher temperature directly to isotropic phase. The solid state modification determines whether a monotropic and an enantiotropic mesophase is observed. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.tca.2014.04.024

文献信息

• Flüssigkristall mit einem eingelagerten pleochroitischen Anthrachinon-Farbstoff und seine Verwendung
  申请人：SIEMENS AKTIENGESELLSCHAFT

  公开号：EP0034832A1

  公开（公告）日：1981-09-02

  Anthrachinon-Farbstoff der allgemeinen Formel mit R1, R3, R4 und R5 = H, OH, OCH3, NO2, NH2 oder NHCH3 und mit R2, R5 = a) Alkyl-, Aryl-, Alkylaryl-, Alkoxyaryl-, Aminoaryl-, Alkylaminoaryl-,Arylaminoaryl-oder oder oder wobei R' = Alkyl-, Aryl-, Amino-, Alkylamino-, Dialkylamino-, Arylamino-, Alkyloxy-, Aryloxy-Rest. Der Farbstoff eignet sich vor allem für Flüssigkristallanzeigen, die mit dem "guest host"-Effekt arbeiten.

  通式如下的蒽醌染料 其中 R1、R3、R4 和 R5 = H、OH、OCH3、NO2、NH2 或 NHCH3，以及 其中 R2、R5 = H、OH、OCH3、 、NH2 或 NHCH3 a) 烷基-、芳基-、烷芳基-、烷氧基芳基-、氨基芳基-、烷基氨基芳基-、芳基氨基芳基-或 或 或 其中 R' = 烷基、芳基、氨基、烷基氨基、二烷基氨基、芳基氨基、烷氧基、芳氧基基。 这种着色剂特别适用于具有 "客体宿主 "效应的液晶显示器。
• Flüssigkristall mit einem eingelagerten pleochroitischen Anthrachinon-Farbstoff und Verfahren zur Herstellung des Farbstoffes
  申请人：SIEMENS AKTIENGESELLSCHAFT

  公开号：EP0055989A2

  公开（公告）日：1982-07-14

  Flüssigkristall mit einem eingelagerten pleochroitischen Anthrachinon-Farbstoff und Verfahren zur Herstellung de Farbstoffes. Der Farbstoff hat die allgemeine Formel Solche Flüssigkristallmischungen werden vor allem bei Flüssigkristallanzeigen auf der Basis der "guest-host"-Effektes verwendet. Die Reste R1, R3, R4, R6 stehen für H, OH, OCH3, NH2, NO2, NHCH3. Es gilt wobei R7 ein Alkyl-, Aryl-, Amino-, Alkylamino, Diakylamino, Arylamino-, Alkyloxy-, Aryloxy-Rest ist, mit der Maßgabe, daß 1,5-Diamino-4,8-dihydroxy-3,7-di-(4-methoxyphenyl)-anthrachinon ausgenommen ist.

  含有多色蒽醌染料的液晶及其生产工艺。 该染料的通式为 这种液晶混合物主要用于基于 "客主 "效应的液晶显示器。 自由基 R1、R3、R4、R6 分别代表 H、OH、OCH3、NH2、NO2、NHCH3。以下情况适用 其中 R7 是烷基、芳基、氨基、烷基氨基、二酰氨基、芳基氨基、烷氧基或芳氧基自由基，但不包括 1,5-二氨基-4,8-二羟基-3,7-二（4-甲氧基苯基）-蒽醌。
• Synthesis and Characterization of New Liquid Crystals containing a Non-Activated Indolinobenzospiropyranyl Group. Part 4*[1]
  作者：S.-R. Keum、J.-T. Shin、S.-H. Lee、S.-T. Shin

  DOI：10.1080/15421400490434892

  日期：2004.1

  A series of new liquid crystalline compounds, 1', 3', 3'-Trimetylspiro [2H-1-benzopyran-2,2'-indolin]-6-yl 4-(4'-alkoxyphenylazo)benzoate, SP-APAB 1a similar to 1f, has been synthesized. Their liquid crystallines were subjected to thermal analysis on a differential scanning calorimeter (DSC), to texture of phases on a polarizing microscope and to phase transition on an X-ray diffraction and electro-optical measurement. Most of compounds examined exhibit monotropic nematic and SmA liquid crystal phases on cooling from isotropic liquid. Suprisingly, SP-APAB 1c is shown to exhibit monotropic SmC phase in addition. X-ray diffraction study of the layer spacing confirmed that there was a layer spacing in the range of two theta from 2.25 to 2.45 Angstrom on the temperature near the phase transition from SmA to SmC.
• BEZBORODOV V. S.; BUBEL O. N.; KUZMICHKIN P. V., ZH. ORGAN. XIMII, 1980, 16, HO 1, 138-141
  作者：BEZBORODOV V. S.、 BUBEL O. N.、 KUZMICHKIN P. V.

  DOI：——

  日期：——
• US4363743A
  申请人：——

  公开号：US4363743A

  公开（公告）日：1982-12-14