4-(4'-n-decyloxyphenyl)azobenzoic acid | 136954-83-1

• 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'-n-decyloxyphenyl)azobenzoic acid
• 英文别名: 4-(4-decyloxyphenylazo)benzoic acid
• CAS: 136954-83-1
• 化学式: C₂₃H₃₀N₂O₃
• 分子量: 382.503
• InChiKey: ZXZKNKLHEGMLSA-OCOZRVBESA-N

物化性质

• 沸点：
  545.2±30.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.32
• 重原子数：
  28.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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'-n-decyloxyphenyl)azobenzoic 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39%的产率得到4-n-decanoxy-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：

  在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 48.0h， 以50%的产率得到4-(4'-n-decyloxyphenyl)azobenzoic acid
  参考文献：
  名称：

  Long-Range Ordering of Highly Charged Self-Assembled Nanofilaments

  摘要：

  Charged nanoscale filaments are well-known in natural systems such as filamentous viruses and the cellular cytoskeleton. The unique properties of these structures have inspired the design of self-assembled nanofibers for applications in regenerative medicine, drug delivery, and catalysis, among others. We report here on an amphiphile of completely different chemistry based on azobenzene and a quaternary ammonium bromide headgroup that self-assembles into highly charged nanofibers in water and orders into two-dimensional crystals. Interestingly small-angle X-ray scattering (SAXS) shows that these fibers of 5.6 nm cross-sectional diameter order into crystalline arrays with remarkably large interfiber spacings of up to 130 nm. Solution concentration and temperature can be adjusted to control the interfiber spacings, and addition of salt destroyed the crystal packing indicating the electrostatic repulsions are necessary for the observed ordering. Our findings here demonstrate the universal nature of this phenomenon in systems of highly charged nanoscale filaments.

  DOI：

  10.1021/ja5082519

文献信息

• The intrinsic photoferroelectric effect in the smectic C* phase of a chiral azobenzene
  作者：Alexander Saipa、Mikhail A. Osipov、Kenneth W. Lanham、Catherine H. Chang、David M. Walba、Frank Giesselmann

  DOI：10.1039/b602060g

  日期：——

  The ferroelectric properties in the liquid-crystalline smectic C* phase of the chiral mesogenic azobenzene (S)-4-(4-decyloxy-phenylazo)benzoic acid 4-(1-methylhexyloxy)-3-nitro-phenyl ester (‘W470’) were studied and found to be strongly dependent on the intensity of incident light. The light-induced trans to cis isomerization of the azobenzene chromophore which is an intrinsic constituent of this SmC* mesogen leads to a pronounced photoferroelectric effect since the ferroelectric SmC* ordering is considerably disturbed by the presence of bent-shaped cis-isomer molecules: At increasing light intensity a strong decrease of both SmC* order parameters, spontaneous electric polarization Ps and director tilt angle θ, is observed. It is further seen that even the nature of the ferroelectric transition is affected by the photoisomerization which leads to a crossover from the nearly tricritrical transition observed in the absence of light to a typical second-order transition. This result is interpreted theoretically taking into account a coupling between the director tilt and the biaxial order parameter which is strongly affected by the light-induced generation of the bent-shaped cis-isomers. The dynamics of the intrinsic photoferroelectric effect in W470 was studied by time-resolved measurements of spontaneous polarisation and director tilt.

  手性介晶偶氮苯（S）-4-（4-癸氧基苯偶氮）苯甲酸4-（1-甲基己氧基）-3-硝基苯酯（‘W470’）的液晶层列C*相中的铁电性质被研究，并发现这些性质强烈依赖于入射光强度。偶氮苯发色团是这种SmC*介晶的内在组成部分，其光诱导的反式到顺式异构化导致了明显的光铁电效应，因为弯曲的顺式异构分子存在，使得铁电性的SmC*有序性大大受到干扰：随着光强度的增加，可以看到SmC*序参数、自发极化Ps和取向倾斜角θ都显著减少。进一步可以看到，甚至铁电相变的性质也受到光异构化的影响，导致在没有光的情况下观察到的接近三临界点的转变转变为典型的二级转变。这一结果在理论上被解释为考虑到取向倾斜和受光诱导的弯曲顺式异构体的产生强烈影响的二轴有序参数之间的耦合。通过对自发极化和取向倾斜进行时间分辨测量，研究了W470中内在光铁电效应的动力学。
• Fluorescence Changes of Glycyl-Tryptophan Peptide in the Presence of Some Newly Synthesized Azobenzene Compounds
  作者：Catalina-Ionica Ciobanu、Laura Habasescu、Dan Scutaru、Gabi Drochioiu

  DOI：10.2174/1570178612666150107235907

  日期：2015.2.13

  Five newly synthesized bent-shaped compounds containing azobenzene chromophores have been prepared by resorcinol esterification with 4-(4-alkyloxyphenylazo) benzoic acid using DCC and DMAP. The structure of newly synthesized compounds was confirmed by MS and FT-IR spectroscopy. In addition, NMR spectroscopy also established the purity of these compounds. According to their azo-type chemical structure, the newly synthesized compounds are expected to be highly fluorescent. Consequently, their absorption and fluorescence properties were investigated using UVVis and fluorescence spectroscopy. The present paper also investigates the fluorescence evolution of glycyl-L-tryptophan dipeptide at different concentrations of the newly synthesized bent-shaped compounds. The intensity of their fluorescence band over 400 nm depends much on individual structures. Since the investigated compounds could have optical properties characteristic to liquid crystals, the interaction with fluorescent peptides, such as glycyl-tryptophan or proteins might enhance their utility.

  通过间苯二酚与 4-(4-alkyloxyphenylazo)苯甲酸的酯化反应，使用 DCC 和 DMAP 制备了五种新合成的含偶氮苯发色团的弯曲状化合物。质谱和傅立叶变换红外光谱证实了新合成化合物的结构。此外，核磁共振光谱也确定了这些化合物的纯度。根据其偶氮型化学结构，预计新合成的化合物具有高荧光性。因此，本文使用紫外可见光谱和荧光光谱研究了它们的吸收和荧光特性。本文还研究了新合成的弯曲形化合物在不同浓度下甘氨酰-L-色氨酸二肽的荧光演变。它们在 400 纳米以上的荧光带强度在很大程度上取决于各自的结构。由于所研究的化合物可能具有液晶的光学特性，因此与荧光肽（如甘氨酰-色氨酸或蛋白质）的相互作用可能会提高它们的实用性。
• 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：——
• KALINNIKOVA, T. E.;KRAJNOVA, L. P.;POCHEKUEV, A. YU.;FOFANOVA, N. I., SOVERSH. PROTSESSOV KRASHENIYA I METODOV SINTEZA KRASITELEJ, IVANOVO, 198+
  作者：KALINNIKOVA, T. E.、KRAJNOVA, L. P.、POCHEKUEV, A. YU.、FOFANOVA, N. I.

  DOI：——

  日期：——