2-(1-芘基甲基)-2-乙酰氨基丙二酸二乙酯 | 568599-06-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: 2-(1-芘基甲基)-2-乙酰氨基丙二酸二乙酯
• 英文名称: diethyl 2-(1-pyrenylmethyl)-2-acetamidomalonate
• 英文别名: Diethyl-2-(1-pyrenylmethyl)-2-acetamidomalonate；diethyl 2-acetamido-2-(pyren-1-ylmethyl)propanedioate
• CAS: 568599-06-4
• 化学式: C₂₆H₂₅NO₅
• 分子量: 431.488
• InChiKey: VBZWFHIEAJWVEA-UHFFFAOYSA-N

物化性质

• 熔点：
  135-140 °C
• 沸点：
  630.0±55.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1-芘基甲基)-2-乙酰氨基丙二酸二乙酯 在 氢氧化钾 、 sodium hydroxide 、 aminoacylase 、 cobalt(II) chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 66.0h， 生成 (2S)-2-氨基-3-(1-芘基)丙酸
  参考文献：
  名称：

  A Non-Covalent Strategy for the Assembly of Supramolecular Photocurrent-Generating Systems

  摘要：

  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.

  DOI：

  10.1021/ja0289548
• 作为产物：
  描述：

  1-芘甲醇 在 三溴化磷 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 22.0h， 生成 2-(1-芘基甲基)-2-乙酰氨基丙二酸二乙酯
  参考文献：
  名称：

  A Non-Covalent Strategy for the Assembly of Supramolecular Photocurrent-Generating Systems

  摘要：

  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.

  DOI：

  10.1021/ja0289548

文献信息

• Cyclic peptide structures for molecular scale electronic and photonic devices
  申请人：——

  公开号：US20030144185A1

  公开（公告）日：2003-07-31

  The present invention discloses a family of cyclic peptide monomers and supramolecular cyclic peptide structures comprising chromophore residues which possess electronic and electro-optic properties for producing molecular scale electronic and photonic devices made from such materials. More particularly, this invention provides for cyclic peptide nanotube structures formed from a plurality of stacked cyclic peptides comprising chromophore residues that provide molecular scale electronic conductivity and non linear optical behavior. The stackable cyclic peptide is represented by the general formula 1 wherein R 1 is H, CH 3 or alkyl; wherein R 2 a chromophore or a rigid and flat extended conjugated pi system other than benzene; wherein R 3 is H, CH 3 or a polar or non-polar organic functional group used for controlling peptide stacking and solubility; wherein n equals 1 or 2; wherein m equals 4 or 6; and wherein a first adjacent amino acid residue has an &agr;-carbon chirality of L and a second adjacent amino acid residue has an &agr;-carbon chirality of D.

  本发明揭示了一系列环肽单体和超分子环肽结构，包括具有电子和电光性能的色团残基，用于制造由此类材料制成的分子尺度电子和光子器件。更具体地，本发明提供了由多个堆叠的环肽组成的环肽纳米管结构，其中包括提供分子尺度电导和非线性光学行为的色团残基。可堆叠的环肽由通式1表示，其中R1为H、CH3或烷基；R2为色团或刚性和扁平的扩展共轭π体系，而非苯；R3为H、CH3或用于控制肽堆叠和溶解度的极性或非极性有机功能基团；n等于1或2；m等于4或6；第一个相邻氨基酸残基具有L的α-碳手性，第二个相邻氨基酸残基具有D的α-碳手性。
• Cyclic peptide nanotube structures for molecular scale electronic and photonic devices
  申请人：McGimpsey Grant William

  公开号：US20050124535A1

  公开（公告）日：2005-06-09

  The present invention discloses a family of cyclic peptide monomers and supramolecular cyclic peptide structures comprising chromophore residues which possess electronic and electro-optic properties for producing molecular scale electronic and photonic devices made from such materials. More particularly, this invention provides for cyclic peptide nanotube structures formed from a plurality of stacked cyclic peptides comprising chromophore residues that provide molecular scale electronic conductivity and non linear optical behavior. The stackable cyclic peptide is represented by the general formula of m repeating amino acid residue pairs where n equals 1 or 2, m equals 4 or 6, R A and R D are either H, CH 3 or an alkyl, where at least one R B or R E in at least one repeating residue pair is a chromophore, where R C and R F are either H, CH 3 or a polar or non-polar organic functional group used for controlling peptide stacking, nanotube formation and solubility, and where a first adjacent amino acid residue has an α-carbon chirality of L and a second adjacent amino acid residue has an α-carbon chirality of D.

  本发明披露了一类环肽单体和超分子环肽结构，包括具有电子和电光性质的色团残基，用于制备由此类材料制成的分子尺度电子和光子器件。更具体地，本发明提供了由多个堆叠的含有色团残基的环肽组成的环肽纳米管结构，其提供了分子尺度的电子传导和非线性光学行为。可堆叠的环肽由m个重复的氨基酸残基对表示，其中n等于1或2，m等于4或6，RA和RD为H、CH3或烷基，其中至少一个重复残基对中的RB或RE为色团，RC和RF为H、CH3或用于控制肽堆叠、纳米管形成和溶解度的极性或非极性有机功能基团，其中第一个相邻氨基酸残基具有Lα-碳手性，第二个相邻氨基酸残基具有Dα-碳手性。
• Non-covalent assembly of multilayer thin film supramolecular structures
  申请人：——

  公开号：US20040110009A1

  公开（公告）日：2004-06-10

  Self-assembled monolayers and multilayer thin film structures were assembled from multiple components that were linked non-covalently by metal-ligand complexation. Non-covalently assembled multicomponent films assembly my the present method obviate problems associated with the covalent assembly of SAMs and multilayer thin film structures from large molecules. In one preferred embodiment, the disclosed film structures comprise 2,6 pyridinedicarboxylate ligands attached to an alkanethiol, which form a self-assembled monolayer on gold. The SAM is subsequently functionalized by sequential deposition of metal ions and ligands, allowing incorporation of one or more chromophores, photooxiding compounds or photoreducing to form multilayer film structures. Transition metals, lanthanide metals and other metals of varying charge may be employed in complexing with with 2,6 pyridinedicarboxylate ligands to form stable ordered structures. The non-covalent assembly method provides for multilayer film formation from mixtures of metal ions and a varying number of film layers. Multilayer thin film structures exhibit stable cathodic photocurrent generation in the presence of methyl viologen or EDTA in solution.

  自组装单分子层和多层薄膜结构是由多个组分非共价地通过金属配体络合连接而组装而成的。通过本方法非共价组装的多组分薄膜组装消除了由大分子的共价组装形成的SAMs和多层薄膜结构所带来的问题。在一个优选实施例中，所公开的薄膜结构包括连接到烷硫醇的2,6-吡啶二甲酸配体，其在金上形成自组装单分子层。随后，通过金属离子和配体的顺序沉积来功能化SAM，从而允许将一个或多个发色团、光氧化化合物或光还原化合物并入其中，形成多层膜结构。过渡金属、镧系金属和其他带电金属可以用于与2,6-吡啶二甲酸配体形成稳定有序结构的络合。非共价组装方法提供了从金属离子和不同数量的薄膜层混合物中形成多层薄膜的方法。多层薄膜结构在存在甲基紫或EDTA的溶液中表现出稳定的阴极光电流产生。
• US6893716B2
  申请人：——

  公开号：US6893716B2

  公开（公告）日：2005-05-17
• US6902720B2
  申请人：——

  公开号：US6902720B2

  公开（公告）日：2005-06-07