trans-MUA | 167110-88-5

• 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: trans-MUA
• 英文别名: trans-4-(4'-(phenylazo)phenoxy)undecane-1-thiol；11-(4-(Phenylazo)phenoxy)undecane-1-thiol；trans-4-(11-mercaptoundecanoxy)azobenzene
• CAS: 167110-88-5
• 化学式: C₂₃H₃₂N₂OS
• 分子量: 384.586
• InChiKey: CDQZNOJMHCNKQH-OCOZRVBESA-N

物化性质

• 沸点：
  520.2±20.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.92
• 重原子数：
  27.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  33.95
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  trans-MUA 以 乙醇 为溶剂， 反应 48.0h， 生成 cis-4-(4'-(phenylazo)phenoxy)undecane-1-thiol
  参考文献：
  名称：

  Photon-Gated Electron Transfer in Two-Component Self-Assembled Monolayers

  摘要：

  The preparation and characterization of a photoactive, two-component self-assembled monolayer (SAM) consisting of 99:1 cis-p-(C6H5)N=N(C6H4)O(CH2)(11)SH) (1) and trans-p,p-Fc(C6H4)N=N(C6H4)(CH2)(4)SH (Fc = C5H4FeC5H5; 2) are reported. With this SAM, electron transfer between solution ferrocyanide and the Au substrate is forced to occur through mediating ferrocenyl sites in the film, resulting in a diode-like response. However, by photochemically converting large "footprint" cis-l to the smaller footprint trans-1, the free volume within the film is increased, thereby allowing for direct electron transfer between the solution ferrocyanide and the electrode surface and a normal electrochemical response (i.e. i(pa) = i(pc)). All states of the film have been characterized by cyclic voltammetry, FTIR spectroscopy, and differential capacitance measurements. All data from these techniques are consistent with the conclusion that cis-trans azobenzene isomerization within the monolayer results in increased film porosity, which reduces the film's ability to block the access of solution redox-active species to the underlying Au electrode surface. This novel two-component structure establishes the concept for a new type of molecule-based electronic device, a "photoswitchable diode" that is capable of amplifying the signal associated with a photodriven event via an electrochemical response. With such a system, a small number of photons can release a relatively large number of electrons from the solution electron reservoir. Significantly, this system shows how one can regulate electron-transfer events involving SAMs through photochemical control over film structure and free volume.

  DOI：

  10.1021/jp983460b
• 作为产物：
  描述：

  (E)-4-Phenylazophenol 在 氢氧化钾 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 trans-MUA
  参考文献：
  名称：

  Au(111) 上偶氮苯硫醇的高度有序自组装单层膜：同步加速器面内 X 射线衍射、原子力显微镜和表面增强拉曼光谱的电化学性质和结构表征

  摘要：

  报道了 p-HS(CH{sub 2}){sub 11}OC{sub 6}H{sub 4}N=NC{sub 6}H{sub 5}，化合物 1d 的合成和表征。化合物 1d 自组装到 Au(111) 衬底上形成高度有序的单层膜。Au(111)/云母上 1d 的自组装单层膜 (SAM) 已通过椭偏仪、表面增强拉曼光谱 (SERS) 和原子力显微镜 (AFM) 进行表征。我们还通过同步加速器面内 X 射线衍射 (XRD) 测量报告了块状单晶 Au(111) 上 1d SAM 的表征。AFM 和面内 XRD 表明 1d 的 SAM 由 1d 的域组成，这些域形成与底层 Au(111) 晶格不相称的六边形晶格（4.50 {+-} 0.06 A 最近邻间距）。提出了一个模型来描述 SAM 结构。在这样的模型中，位于一组向内倾斜的烷基表面束缚基团上的有序偶氮苯部分的小束（近 80 个分子）构成了各个域。1d

  DOI：

  10.1021/ja00127a021

文献信息

• Hepatitis C Virus Inhibitors
  申请人：Lopez Omar D.

  公开号：US20100249190A1

  公开（公告）日：2010-09-30

  This disclosure concerns novel compounds of Formula (I) as defined in the specification and compositions comprising such novel compounds. These compounds are useful antiviral agents, especially in inhibiting the function of the NS5A protein encoded by Hepatitis C virus (HCV). Thus, the disclosure also concerns a method of treating HCV related diseases or conditions by use of these novel compounds or a composition comprising such novel compounds.

  这项披露涉及到规范中定义的Formula (I)的新化合物以及包含这些新化合物的组合物。这些化合物是有用的抗病毒剂，特别是在抑制由丙型肝炎病毒（HCV）编码的NS5A蛋白的功能方面。因此，该披露还涉及通过使用这些新化合物或包含这些新化合物的组合物来治疗HCV相关疾病或症状的方法。
• Writing Self-Erasing Images using Metastable Nanoparticle “Inks”
  作者：Rafal Klajn、Paul J. Wesson、Kyle J. M. Bishop、Bartosz A. Grzybowski

  DOI：10.1002/anie.200901119

  日期：2009.9.7

  Mission Impossible: Metal nanoparticles (NPs) coated with photoresponsive ligands are used as “inks” for self‐erasing “paper” whereby light‐induced self‐assembly of the NPs is transduced into local color changes (see picture). Depending on the degree of self‐assembly, multicolor images can be written using only one type of NP ink. Duration of image erasure is regulated by the surface concentration

  不可能完成的任务：涂有光响应性配体的金属纳米颗粒（NP）用作自擦除“纸”的“墨水”，从而将光诱导的NP的自组装转换为局部颜色变化（参见图片）。根据自组装的程度，只能使用一种类型的NP墨水写入多色图像。图像擦除的持续时间取决于光敏基团的表面浓度，范围从数秒到数天不等。
• Structure of Alkyl and Perfluoroalkyl Disulfide and Azobenzenethiol Monolayers on Gold(111) Revealed by Atomic Force Microscopy
  作者：M. Jaschke、H. Schönherr、H. Wolf、H.-J. Butt、E. Bamberg、M. K. Besocke、H. Ringsdorf

  DOI：10.1021/jp952355o

  日期：1996.1.1

  The structure of various self-assembled thiol and disulfide monolayers on gold(111) has been studied with the atomic force microscope. The aim was to analyze the factors which determine the two-dimensional structure of the molecules. Monolayers were formed from different disulfides and thiols: long-chain alkyl and perfluoroalkyl esters of bis(2-hydroxyethyl) disulfide, several azobenzenethiols, and octadecanethiol. Three classes of two-dimensional structures could be distinguished: (1) commensurate monolayers, which were dominated by the underlying gold(111) lattice; an example is n-alkanethiol monolayers; (2) incommensurate or at most high-order commensurate monolayers, whose orientation was still determined by the gold(111) substrate; this type of monolayer probably occurred with all disulfides investigated; (3) incommensurate monolayers, whose orientation was arbitrary and not determined by the underlying gold(111). Monolayers of azobenzenthiols belonged to this class.
• Metastable Nanoparticle Ink Compositions and Images Made Therefrom
  申请人：Grzybowski Bartosz A.

  公开号：US20100328410A1

  公开（公告）日：2010-12-30

  Self-erasing inks in which both the printing and self-erasure of color images can be controlled by the dynamic/non-equilibrium aggregation of photoresponsive surface-coated nanoparticles contained in a carrier film are provided. The aggregation is a reversible aggregation that is triggered by a photo-induced transformation in ligands within the surface coating on the nanoparticles. Methods for forming images using the inks are also provided.
• US8496323B2
  申请人：——

  公开号：US8496323B2

  公开（公告）日：2013-07-30