4-hydroxy-2'-methyl-4'-bromoazobenzene | 918150-38-6

• 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-2'-methyl-4'-bromoazobenzene
• 英文别名: 4-[2-(4-Bromo-2-methylphenyl)hydrazinylidene]cyclohexa-2,5-dien-1-one；4-[(4-bromo-2-methylphenyl)diazenyl]phenol
• CAS: 918150-38-6
• 化学式: C₁₃H₁₁BrN₂O
• 分子量: 291.147
• InChiKey: LTFSYDSZGNJUAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  444.5±45.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  45
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-2'-methyl-4'-bromoazobenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Two-photon actuation of crosslinked liquid-crystalline polymers utilizing energy transfer system

  摘要：

  We prepared crosslinked azotolane liquid-crystalline polymer (LCP) films doped with a stilbene derivative (two-photon chromophore) utilizing an interpenetrating polymer network (IPN) structure. The IPN films bend toward the light source upon irradiation with femtosecond laser pulses at 600nm, which can excite the stilbene derivative by two-photon absorption. The bending speed of the IPN films increases with the square of the laser pulse intensity, which is compelling evidence for the two-photon processes.

  DOI：

  10.1080/15421406.2018.1466241
• 作为产物：
  描述：

  4-碘苯酚 、 2-甲基-4-溴苯胺 在 tetrafluoroboric acid 、 potassium carbonate 、 sodium nitrite 作用下， 生成 4-hydroxy-2'-methyl-4'-bromoazobenzene
  参考文献：
  名称：

  Visible Light Induced Bending Behavior of Crosslinked Liquid Crystal Polymers Containing Azotolane with a Longer Spacer

  摘要：

  One azotolane-containing acrylate monomer with a longer spacer and a non-azotolane crosslinker were synthesized. Crosslinked liquid crystal polymer (CLCP) films were obtained by thermal polymerization of the mixture of the monomer and the crosslinker with a molar ratio of 2:8. Thermodynamic and mesomorphic properties of the monomer, the crosslinker and the CLCP films were characterized by DSC and POM. The CLCP films showed a low glass transition temperature which ensured them to bend at room temperature upon visible light irradiation. Besides, the films have a faster bending speed compared with the previously-reported azotolane-containing CLCP films with a shorter spacer.

  DOI：

  10.1080/15421406.2014.940566

文献信息

• Can sunlight drive the photoinduced bending of polymer films?
  作者：Ruoyuan Yin、Wanxian Xu、Mizuho Kondo、Chu-Chun Yen、Jun-ichi Mamiya、Tomiki Ikeda、Yanlei Yu

  DOI：10.1039/b904973h

  日期：——

  Photoinduced bending and unbending behavior of crosslinked liquid-crystalline polymers containing azotolane moieties in side chains occurred upon irradiation with sunlight, according to the trans–cisphotoisomerization of the azotolane moieties.

  根据偶氮杂环部分的反式-顺式光异构化，侧链中含有偶氮杂环部分的交联液晶聚合物在阳光照射下发生光致弯曲和不弯曲行为。
• KR101869388
  申请人：——

  公开号：——

  公开（公告）日：——
• Red-Light-Controllable Liquid-Crystal Soft Actuators via Low-Power Excited Upconversion Based on Triplet–Triplet Annihilation
  作者：Zhen Jiang、Ming Xu、Fuyou Li、Yanlei Yu

  DOI：10.1021/ja406020r

  日期：2013.11.6

  A red-light-controllable soft actuator has been achieved, driven by low-power excited triplet-triplet annihilation-based upconversion luminescence (TTA-UCL). First, a red-to-blue TTA-based upconversion system with a high absolute quantum yield of 9.3 +/- 0.5% was prepared by utilizing platinum(II) tetraphenyltetrabenzoporphyrin (PtTPBP) as the sensitizer and 9,10-bis(diphenylphosphoryl)anthracene (BDPPA) as the annihilator. In order to be employed as a highly effective phototrigger of photodeformable cross-linked liquid-crystal polymers (CLCPs), the PtTPBP&BDPPA system was incorporated into a rubbery polyurethane film and then assembled with an azotolane-containing CLCP film. The generating assembly film bent toward the light source when irradiated with a 635 nm laser at low power density of 200 mW cm(-2) because the TTA-UCL was effectively utilized by the azotolane moieties in the CLCP film, inducing their trans-cis photoisomerization and an alignment change of the mesogens via an emission-reabsorption process. It is the first example of a soft actuator in which the TTA-UCL is trapped and utilized to create photomechanical effect. Such advantages of using this novel red-light-controllable soft actuator in potential biological applications have also been demonstrated as negligible thermal effect and its excellent penetration ability into tissues. This work not only provides a novel photomanipulated soft actuation material system based on the TTA-UCL technology but also introduces a new technological application of the TTA-based upconversion system in photonic devices.
• NIR-Light-Induced Deformation of Cross-Linked Liquid-Crystal Polymers Using Upconversion Nanophosphors
  作者：Wei Wu、Liming Yao、Tianshe Yang、Ruoyuan Yin、Fuyou Li、Yanlei Yu

  DOI：10.1021/ja2043276

  日期：2011.10.12

  When upconversion nanophosphors were incorporated into an azotolane-containing cross-linked liquid-crystal polymer film, the resulting composite film generated fast bending upon exposure to continuous-wave near-IR light at 980 nm. This occurs because the upconversion luminescence of the nanophosphors leads to trans-cis photoisomerization of the azotolane units and an alignment change of the mesogens. The bent film completely reverted to the initial flat state after the light source was removed.