ethyl 4-((4-heptyloxyphenyl)diazenyl)benzoate | 139056-50-1

• 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: ethyl 4-((4-heptyloxyphenyl)diazenyl)benzoate
• 英文别名: ethyl 4-(4'-heptoxyazobenzene)benzoate；Ethyl 4-[(4-heptoxyphenyl)diazenyl]benzoate；ethyl 4-[(4-heptoxyphenyl)diazenyl]benzoate
• CAS: 139056-50-1
• 化学式: C₂₂H₂₈N₂O₃
• 分子量: 368.476
• InChiKey: PNYLHTPGPWSHSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-((4-heptyloxyphenyl)diazenyl)benzoate 在 氯化亚砜 、 sodium hydroxide 作用下， 生成 4-((4-(heptyloxy)phenyl)azo)benzoyl chloride
  参考文献：
  名称：

  Synthesis and Physico-Chemical Properties for 2-Oxochromen-6-yl 4-(4-Alkoxyphenylazo)benzoates

  摘要：

  This paper describes the preparation and thermal properties for homologous series of 2-oxochromen-6-yl 4-(4-alkoxyphenylazo)benzoates (compounds 1-n). Compounds 1-n show nematic phase exclusively, where the nematic-isotropic phase transition temperatures are between 293 degrees C for 1-4 and 256 degrees C for 1-8. Interestingly, compound 1-8 exhibits smectic A and re-entrant nematic phases in addition to the nematic one. The smectic A phase are characterized using a small angle X-ray diffraction study, indicating the smectic A phase has a partially bilayer molecular arrangement.

  DOI：

  10.1080/15421400903060557
• 作为产物：
  描述：

  对氨基苯甲酸 在 盐酸 、 硫酸 、 potassium carbonate 、 sodium nitrite 作用下， 以 水 、 3-戊酮 为溶剂， 生成 ethyl 4-((4-heptyloxyphenyl)diazenyl)benzoate
  参考文献：
  名称：

  Synthesis and Physico-Chemical Properties for 2-Oxochromen-6-yl 4-(4-Alkoxyphenylazo)benzoates

  摘要：

  This paper describes the preparation and thermal properties for homologous series of 2-oxochromen-6-yl 4-(4-alkoxyphenylazo)benzoates (compounds 1-n). Compounds 1-n show nematic phase exclusively, where the nematic-isotropic phase transition temperatures are between 293 degrees C for 1-4 and 256 degrees C for 1-8. Interestingly, compound 1-8 exhibits smectic A and re-entrant nematic phases in addition to the nematic one. The smectic A phase are characterized using a small angle X-ray diffraction study, indicating the smectic A phase has a partially bilayer molecular arrangement.

  DOI：

  10.1080/15421400903060557

文献信息

• Switching Chirophilic Self‐assembly: From <i>meso</i> ‐structures to Conglomerates in Liquid and Liquid Crystalline Network Phases of Achiral Polycatenar Compounds
  作者：Mohamed Alaasar、Yu Cao、Yan Liu、Feng Liu、Carsten Tschierske

  DOI：10.1002/chem.202201857

  日期：2022.12

  The change of the interhelical self-assembly from enantiophilic to enantiophobic takes place by reduction of the alkyl chain length and leads to a phase transition from the achiral double gyroid via a tetragonal phase to a chiral triple network phase, associated with a transition from an achiral to a mirror symmetry broken liquid.

  螺旋间自组装从亲对映体到疏对映体的变化是通过烷基链长度的减少发生的，并导致从非手性双螺旋体通过四方相到手性三网络相的相变，与从非手性的转变相关为镜像对称破损液体。
• Monotropic or enantiotropic mesophases? Liquid-crystalline and solid state polymorphism 4-Chloro-1,3-phenylene bis-[4-(4-alkyloxyphenylazo)benzoates
  作者：Izabela Niezgoda、Damian Pociecha、Zbigniew Galewski

  DOI：10.1016/j.tca.2014.04.024

  日期：2014.7

  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.
• Design, synthesis and liquid crystalline behavior of ethyl 4-((4-alkoxyphenyl)diazenyl)benzoates
  作者：Hasnain Mehmood、Zahoor Ahmad、Tashfeen Akhtar、Humaira M. Siddiqi、Asma Iqbal、Shahid Hameed、Muhammad N. Tahir

  DOI：10.1080/15421406.2018.1442779

  日期：2018.3.24

  A series of ethyl 4-((4-alkoxyphenyl)diazenyl)benzoate is synthesized and the liquid crystalline behavior studied. Synthesized compounds are characterized by FTIR, H-1-NMR, Mass and single crystal XRD. Differential scanning calorimetry was carried out to study the phase transitions and enthalpy changes. Polarizing optical microscopy revealed the mesogenic properties. These techniques revealed that three compounds (2a, 2b, 2f) exhibit liquid crystalline properties in the range of 80-104 degrees C. POM exhibiting focal conical fan like texture which revealed the presence of smectic phases suggestive of their use in LCD and temperature sensing devices, besides 2c can be used as green emitter in OLEDs.
• Syntheses, Electronic Structures, and Dichroic Behavior of Dinuclear Cyclopalladated Complexes of Push−Pull Azobenzenes
  作者：Octavia A. Blackburn、Benjamin J. Coe

  DOI：10.1021/om101189f

  日期：2011.4.25

  Eight new chloride-/acetate-bridged dimeric Pd-II complexes have been synthesized by using 4-heptoxyazobenzenes 4'-substituted with groups of varying electron-withdrawing strength (NO2, CN, F, or CO2Et). The effects of charge density distribution and the bridging ligand on the relative proportions of structural and geometrical isomers produced is explored by using NMR spectroscopy. UV-vis spectroscopy reveals a single low-energy absorption for each proligand but three distinct bands for each of the complexes. The origins of the observed absorptions are inferred from the effects of changing the bridging ligands and corroborated by time-dependent density functional theory (TD-DFT) calculations. Dichroic ratio (DR) measurements in two different liquid-crystal (LC.) hosts show decreased performance upon complexation, although the results are notably wavelength dependent. The lowest energy absorption band, associated with intraligand charge-transfer transitions, displays superior dichroism with respect to the adjacent band at higher energy. The transition dipole moment directions calculated via TD-DFT correlate with the observed DR results, implying a decrease in alignment within the LC hosts for the complexes with respect to their proligands.