diethyl 4-[(10-bromodecyl)oxy]pyridine-2,6-dicarboxylic acid | 668461-84-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: diethyl 4-[(10-bromodecyl)oxy]pyridine-2,6-dicarboxylic acid
• 英文别名: diethyl 4-(10-bromodecyloxy)-pyridine-2,6-dicarboxylate；Diethyl 4-[(10-bromodecyl)oxy]pyridine-2,6-dicarboxylate；diethyl 4-(10-bromodecoxy)pyridine-2,6-dicarboxylate
• CAS: 668461-84-5
• 化学式: C₂₁H₃₂BrNO₅
• 分子量: 458.393
• InChiKey: GLCOEAIOZRLCSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  74.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 4-[(10-bromodecyl)oxy]pyridine-2,6-dicarboxylic acid 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 24.25h， 生成 4-[(10-mercaptodecyl)oxy]pyridine-2,6-dicarboxylic acid
  参考文献：
  名称：

  Non-Covalent Assembly of a Photoswitchable Surface

  摘要：

  A noncovalently bound multilayered thin film in which individual layers are linked by metal ligand interactions undergoes a photochemically initiated permanent change in surface wettability. The film consists of three separate layers: a SAM on gold of 4-[(10-mercaptodecyl)oxy]pyridine-2,6-dicarboxylic acid, a layer of Cu(II) ions that are deposited onto the SAM and bind symmetrically in the site provided by the two carboxylate groups and the pyridyl nitrogen atom, and a layer of cis-2,2'-dipyridylethylene, which caps the Cu(II) layer by complexation through both pyridyl nitrogen atoms (Film I). Photoexcitation of the film in chloroform at 300 nm leads to substantial cis-trans isomerization as indicated by conductivity, impedance, grazing incidence IR, and contact angle measurements. The latter show a decrease in contact angle (increase in wettability) of 17 degrees , which is attributed to exposure of both the underlying Cu(II) layer and one of the pyridyl ring nitrogen atoms following isomerization to the trans isomer.

  DOI：

  10.1021/ja039230e
• 作为产物：
  描述：

  4-氧代-1,4-二氢-2,6-吡啶二甲酸 在 氯化亚砜 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 42.0h， 生成 diethyl 4-[(10-bromodecyl)oxy]pyridine-2,6-dicarboxylic acid
  参考文献：
  名称：

  Non-Covalent Assembly of a Photoswitchable Surface

  摘要：

  A noncovalently bound multilayered thin film in which individual layers are linked by metal ligand interactions undergoes a photochemically initiated permanent change in surface wettability. The film consists of three separate layers: a SAM on gold of 4-[(10-mercaptodecyl)oxy]pyridine-2,6-dicarboxylic acid, a layer of Cu(II) ions that are deposited onto the SAM and bind symmetrically in the site provided by the two carboxylate groups and the pyridyl nitrogen atom, and a layer of cis-2,2'-dipyridylethylene, which caps the Cu(II) layer by complexation through both pyridyl nitrogen atoms (Film I). Photoexcitation of the film in chloroform at 300 nm leads to substantial cis-trans isomerization as indicated by conductivity, impedance, grazing incidence IR, and contact angle measurements. The latter show a decrease in contact angle (increase in wettability) of 17 degrees , which is attributed to exposure of both the underlying Cu(II) layer and one of the pyridyl ring nitrogen atoms following isomerization to the trans isomer.

  DOI：

  10.1021/ja039230e

文献信息

• Films with photoresponsive wettability
  申请人：McGimpsey Grant W.

  公开号：US20050271975A1

  公开（公告）日：2005-12-08

  In various aspects, the present invention provides substantially monolayer thick molecular films with photoresponsive wettability, the molecules of said films comprising a photochromic molecule coordinated to a metal atom, which is coordinated to an organic tethering molecule, surface coupling group, or both, having a group for attachment to a surface of a substrate. In various aspects, the present inventions also provide photochromic articles comprising said films, methods of forming said films, and methods of manufacturing photochromic articles using said films. In various embodiments, provided are molecular films where the photoconversion between configurations of the photochromic molecule is substantially reversible by irradiation with light. In various embodiments, provided are films where the photoconversion is substantially irreversible by irradiation with light.

  在各个方面，本发明提供了具有光致变色润湿性的基本单层厚分子薄膜，所述薄膜的分子包括与金属原子配位的光致变色分子，该金属原子与有机系链分子、表面偶联基团或两者配位，具有用于附着到基底表面的基团。在各个方面，本发明还提供了包含所述薄膜的光致变色物品、形成所述薄膜的方法以及使用所述薄膜制造光致变色物品的方法。在各种实施方案中，提供了分子薄膜，其中光致变色分子构型之间的光电转换在光照射下基本上是可逆的。在各种实施例中，所提供的薄膜在光照射下的光电转换基本上是不可逆的。
• A Non-Covalent Strategy for the Assembly of Supramolecular Photocurrent-Generating Systems
  作者：Ernesto Soto、John C. MacDonald、Christopher G. F. Cooper、W. Grant McGimpsey

  DOI：10.1021/ja0289548

  日期：2003.3.1

  Three photocurrent-generating thin films were assembled on gold surfaces. SAM I was constructed from molecules consisting of an alkyl disulfide group linked covalently to a 12-residue helical peptide and terminated with an alanine residue containing a pyrene chromophore. SAM I served as a benchmark for multilayered films II and III in photocurrent generation experiments. Films II and III were assembled from several components that were linked noncovalently by metal-ligand complexation. Cyclic voltammetry and contact angle measurements suggest that the films consist of ordered layers with relatively few defects. Photoexcitation of SAM I by the output of a 350 nm lamp ( approximately 0.2 mW power incident on the sample) results in current generation in the range 5-10 nA/cm2. Photoexcitation of II and III yields higher current in the range 10-30 nA/cm2, representing a quantum efficiency of approximately 1%. The observation of comparable or higher current from noncovalently assembled multicomponent films indicates that this method of assembly may obviate the problems associated with the covalent assembly of devices from large molecules.
• US7326526B2
  申请人：——

  公开号：US7326526B2

  公开（公告）日：2008-02-05
• Non-Covalent Assembly of a Photoswitchable Surface
  作者：Christopher G. F. Cooper、John C. MacDonald、Ernesto Soto、W. Grant McGimpsey

  DOI：10.1021/ja039230e

  日期：2004.2.1

  A noncovalently bound multilayered thin film in which individual layers are linked by metal ligand interactions undergoes a photochemically initiated permanent change in surface wettability. The film consists of three separate layers: a SAM on gold of 4-[(10-mercaptodecyl)oxy]pyridine-2,6-dicarboxylic acid, a layer of Cu(II) ions that are deposited onto the SAM and bind symmetrically in the site provided by the two carboxylate groups and the pyridyl nitrogen atom, and a layer of cis-2,2'-dipyridylethylene, which caps the Cu(II) layer by complexation through both pyridyl nitrogen atoms (Film I). Photoexcitation of the film in chloroform at 300 nm leads to substantial cis-trans isomerization as indicated by conductivity, impedance, grazing incidence IR, and contact angle measurements. The latter show a decrease in contact angle (increase in wettability) of 17 degrees , which is attributed to exposure of both the underlying Cu(II) layer and one of the pyridyl ring nitrogen atoms following isomerization to the trans isomer.