pentacosa-10,12-diynoic acid (2-diethylamino-ethyl)-amide | 795314-69-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: pentacosa-10,12-diynoic acid (2-diethylamino-ethyl)-amide
• 英文别名: N-(10,12-pentacosadiynoyl)-N',N'-diethylethylenediamine；N-[2-(diethylamino)ethyl]pentacosa-10,12-diynamide
• CAS: 795314-69-1
• 化学式: C₃₁H₅₆N₂O
• 分子量: 472.798
• InChiKey: AZXVQUHZIZQPPY-UHFFFAOYSA-N

物化性质

• 沸点：
  617.8±40.0 °C(Predicted)
• 密度：
  0.909±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  34
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴乙烷 、 pentacosa-10,12-diynoic acid (2-diethylamino-ethyl)-amide 以 硝基甲烷 、 氯仿 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Self-Assembly of Biocidal Nanotubes from a Single-Chain Diacetylene Amine Salt

  摘要：

  We describe the facile two-step synthesis of nanotubes that form pure, well-defined, nanostructured materials. We have synthesized a secondary amine HBr salt as the headgroup of a single-chain diacetylenic lipid. This molecule can form a number of different self-assembled nanostructures in aqueous or organic solvents. In water, this lipid forms a monodisperse preparation of nanotubes at high yields. Partially dissolving a preparation of nanotubes dried from aqueous solution results in a remarkably organized structure that resembles a nanocarpet. Details of the nanotube structure were investigated by scanning electron microscopy, transmission electron microscopy, and small-angle X-ray spectroscopy. The aqueous nanotubes have a cross-sectional diameter of 89 nm. The walls of the tubes are an exquisitely uniform 27 nm thick and are shown to consist of five lipid bilayers with a repeat spacing of 57.8 Angstrom. The chemical structure of the material shows no chiral centers, but suspensions of the nanotubes in an aqueous medium show an unexpected circular dichroism signal. The versatility of this new material as a platform for nanostructure design and synthesis is enhanced by its biocidal activity. This antimicrobial activity along with the regularity the nanostructures will enhance the development of a range of applications from biosensors to artificial retinas.

  DOI：

  10.1021/ja048463i
• 作为产物：
  描述：

  10,12-二十五碳二炔酸 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 pentacosa-10,12-diynoic acid (2-diethylamino-ethyl)-amide
  参考文献：
  名称：

  Self-Assembly of Biocidal Nanotubes from a Single-Chain Diacetylene Amine Salt

  摘要：

  We describe the facile two-step synthesis of nanotubes that form pure, well-defined, nanostructured materials. We have synthesized a secondary amine HBr salt as the headgroup of a single-chain diacetylenic lipid. This molecule can form a number of different self-assembled nanostructures in aqueous or organic solvents. In water, this lipid forms a monodisperse preparation of nanotubes at high yields. Partially dissolving a preparation of nanotubes dried from aqueous solution results in a remarkably organized structure that resembles a nanocarpet. Details of the nanotube structure were investigated by scanning electron microscopy, transmission electron microscopy, and small-angle X-ray spectroscopy. The aqueous nanotubes have a cross-sectional diameter of 89 nm. The walls of the tubes are an exquisitely uniform 27 nm thick and are shown to consist of five lipid bilayers with a repeat spacing of 57.8 Angstrom. The chemical structure of the material shows no chiral centers, but suspensions of the nanotubes in an aqueous medium show an unexpected circular dichroism signal. The versatility of this new material as a platform for nanostructure design and synthesis is enhanced by its biocidal activity. This antimicrobial activity along with the regularity the nanostructures will enhance the development of a range of applications from biosensors to artificial retinas.

  DOI：

  10.1021/ja048463i

文献信息

• Polydiacetylenevesicles functionalized with N-heterocyclic ligands for metal cation binding
  作者：D. Amilan Jose、Burkhard König

  DOI：10.1039/b918452j

  日期：——

  Self assembled poly diacetylene (PDA) based blue vesicles LS-Terpy, LS-DPA, LS-DP and LS-DEA with metal chelating sites have been prepared and characterized. Their response to the presence of metal cations in buffered aqueous solution has been investigated by monitoring changes of colour, UV-Vis absorption and emission. The addition of zinc, manganese, cadmium, mercury or silver salts to solutions of the vesicles induces a colour change from blue to red observable by the naked eye, while the addition of other metal salts, containing ions like Li+, Na+, K+, Mg2+, Ca2+, Cr2+, Ni2+, Fe2+, Co2+, Cu2+ or Pb2+, failed to show any changes. The metal ion coordination selectivity of the ligands is slightly different for the vesicle surface immobilized ligands compared to the reported metal cation binding of the corresponding ligands in solution, which may be due to the special environment at the lipid–solution interface. The vesicles aggregate upon metal ion coordination to the embedded ligands as shown by dynamic light scattering (DLS) particle size analysis. The functionalized PDA vesicles retain their response to the presence of aqueous solutions of metal ions if immobilized in transparent polyvinyl alcohol films or on paper.

  自组装的聚二乙炔（PDA）基蓝色囊泡LS-Terpy、LS-DPA、LS-DP和LS-DEA已被制备并表征。这些囊泡对缓冲水溶液中金属阳离子的存在反应的研究是通过监测颜色、紫外-可见吸收和发射的变化进行的。向囊泡溶液中添加锌、锰、镉、汞或银盐时，观察到颜色从蓝色变化为红色，这种变化是肉眼可见的；而添加其他金属盐（如锂离子、钠离子、钾离子、镁离子、钙离子、铬离子、镍离子、铁离子、钴离子、铜离子或铅离子）则未表现出任何变化。相对于溶液中对应配体与金属阳离子的结合，固态囊泡表面固定的配体对金属离子的配位选择性略有不同，这可能是由于脂质-溶液界面的特殊环境。囊泡在金属离子与嵌入的配体配位后发生聚集，动态光散射（DLS）颗粒大小分析显示了这一点。功能化的PDA囊泡在透明的聚乙烯醇薄膜或纸上固定后，仍然对金属离子的水溶液保持反应。
• End-to-end joining of nanotubes
  申请人：Russell Alan J.

  公开号：US20100137541A1

  公开（公告）日：2010-06-03

  A method for joining nanotubes end-to-end, includes contacting the nanotubes with a joining fluid. The joining fluid has at least one property that is different from at least one property associated with ends of the nanotubes. In one embodiment, the method further includes contacting the nanotubes with a first, treating fluid and removing the bulk first fluid before the nanotubes are contacted with the joining fluid. The joining fluid is immiscible in the treating fluid to effect end-to-end joining of the nanotubes.

  一种将纳米管端对端连接的方法，包括将纳米管与连接液接触。连接液具有至少一种与纳米管端相关的属性不同。在一种实施例中，该方法还包括将纳米管与第一处理液接触，并在纳米管与连接液接触之前去除大部分第一液体。连接液与处理液不相溶，以实现纳米管的端对端连接。
• Self assembled nanostructures and mehods for preparing the same
  申请人：Russell J. Alan

  公开号：US20070232699A1

  公开（公告）日：2007-10-04

  The present invention provides amphiphilic diacetylene compounds, and compositions and self-assembled nanotubes containing the same. Also provided are methods of producing the compounds, compositions, and nanotubes of the invention, and methods of destroying or inhibiting the growth or proliferation of microorganisms using the nanotubes of the present invention.
• US7666911B2
  申请人：——

  公开号：US7666911B2

  公开（公告）日：2010-02-23
• [EN] SELF ASSEMBLED NANOSTRUCTURES AND METHODS FOR PREPARING THE SAME<br/>[FR] NANOSTRUCTURES AUTO-ASSEMBLEES ET LEURS PROCEDES DE LA PREPARATION
  申请人：NANOSEMBLY LLC

  公开号：WO2006132662A2

  公开（公告）日：2006-12-14

  [EN] The present invention provides amphiphilic diacetylene compounds, and compositions and self-assembled nanotubes containing the same. Also provided are methods of producing the compounds, compositions, and nanotubes of the invention, and methods of destroying or inhibiting the growth or proliferation of microorganisms using the nanotubes of the present invention.
  [FR] La présente invention a trait à des composés à base de diacétylène amphiphiles, et à des compositions et des nanostructures auto-assemblées en contenant. L'invention a également trait à des procédés de production des composés, compositions, et nanotubes de l'invention, et à des procédés de destruction ou d'inhibition de la croissance ou la prolifération de micro-organismes mettant en oeuvre les nanotubes de la présente invention.