Thioacetic acid S-[4-(3-dodecyl-4-{3-dodecyl-4-[3-dodecyl-4-(3-dodecyl-4-ethynyl-phenylethynyl)-phenylethynyl]-phenylethynyl}-phenylethynyl)-phenyl] ester | 187870-92-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: Thioacetic acid S-[4-(3-dodecyl-4-{3-dodecyl-4-[3-dodecyl-4-(3-dodecyl-4-ethynyl-phenylethynyl)-phenylethynyl]-phenylethynyl}-phenylethynyl)-phenyl] ester
• 英文别名: S-[4-[2-[3-dodecyl-4-[2-[3-dodecyl-4-[2-[3-dodecyl-4-[2-(3-dodecyl-4-ethynylphenyl)ethynyl]phenyl]ethynyl]phenyl]ethynyl]phenyl]ethynyl]phenyl] ethanethioate
• CAS: 187870-92-4
• 化学式: C₉₀H₁₂₀OS
• 分子量: 1250.01
• InChiKey: ALDGSDIOBVOADE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  35.4
• 重原子数：
  92
• 可旋转键数：
  55
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  碘苯 、 Thioacetic acid S-[4-(3-dodecyl-4-{3-dodecyl-4-[3-dodecyl-4-(3-dodecyl-4-ethynyl-phenylethynyl)-phenylethynyl]-phenylethynyl}-phenylethynyl)-phenyl] ester 在 copper(l) iodide 、 N,N-二异丙基乙胺 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以65%的产率得到Thioacetic acid S-[4-(3-dodecyl-4-{3-dodecyl-4-[3-dodecyl-4-(3-dodecyl-4-phenylethynyl-phenylethynyl)-phenylethynyl]-phenylethynyl}-phenylethynyl)-phenyl] ester
  参考文献：
  名称：

  Insertion, Conductivity, and Structures of Conjugated Organic Oligomers in Self-Assembled Alkanethiol Monolayers on Au{111}

  摘要：

  Alkanethiolate self-assembled monolayers on Au{111} are used for the two-dimensional matrix isolation of conjugated organic thiolates, studied for their potential to act as molecular wires. The conjugated organic molecules are inserted from dilute solution into boundaries between structural domains and at substrate step edges of preassembled n-alkanethiolate monolayers so as to preserve the order of the initial alkanethiolate lattice. In contrast, when both molecules are codeposited from a single solution, the structure of the assembled monolayer shows no ordered molecular lattice of the alkanethiol component. Scanning tunneling microscopy measurements on the isolated conjugated component molecules show them to have enhanced conductivity compared to neighboring alkanethiolates.

  DOI：

  10.1021/ja973448h
• 作为产物：
  描述：

  1-碘-3-硝基苯 在 palladium on activated charcoal 氢氧化钾 、 sodium hydroxide 、 copper(l) iodide 、 三氯化铝 、 亚硝酸特丁酯 、 三氟化硼乙醚 、 氢氟酸 、 四丁基氟化铵 、 氢气 、 potassium carbonate 、 二异丙胺 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 碘甲烷 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二硫化碳 、 乙醇 、 二氯甲烷 、 氯苯 为溶剂， 120.0 ℃ 、448.16 kPa 条件下， 反应 200.0h， 生成 Thioacetic acid S-[4-(3-dodecyl-4-{3-dodecyl-4-[3-dodecyl-4-(3-dodecyl-4-ethynyl-phenylethynyl)-phenylethynyl]-phenylethynyl}-phenylethynyl)-phenyl] ester
  参考文献：
  名称：

  Rapid Solution and Solid Phase Syntheses of Oligo(1,4-phenylene ethynylene)s with Thioester Termini:  Molecular Scale Wires with Alligator Clips. Derivation of Iterative Reaction Efficiencies on a Polymer Support

  摘要：

  The syntheses of soluble oligo(2-alkyl-1,4-phenylene ethynylene)s via an iterative divergent/ convergent approach starting from 1-(diethyltriazyl)-3-alkyl-4-[(trimethyl are described. When the solublizing alkyl group is an ethyl substituent, the monomer, dimer, tetramer, and octamer can be synthesized. The octamer, however, is only minimally soluble. When the alkyl substituent is 3-ethylheptyl or dodecyl, the compounds are easily dissolved even at the 16-mer stage. The 16-mer is 128 Angstrom long in its near-linear extended conformation. At each stage in the iteration, the length of the framework doubles. Only three sets of reaction conditions are needed for the entire iterative synthetic sequence: an iodination, a protodesilylation, and a Pd/Cu-catalyzed cross coupling. Synthesis of the dodecyl-containing 16-mer was also achieved on Merrifield's resin using the iterative divergent/convergent approach. The oligomers were characterized spectroscopically and by mass spectrometry. The optical properties are presented which show that at the octamer stage, the optical absorbance maximum is nearly saturated. The size exclusion chromatography values for the number average weights, relative to polystyrene, illustrate the tremendous differences in the hydrodynamic volume of these rigid rod oligomers verses the random coils of polystyrene. These differences become quite apparent at the octamer stage. Equations were derived for assessing the efficiency of the polymer-supported reactions based on resin weight; differences, molar concentration differences, and elemental analysis data. Each of these methods' limitations are discussed. Attachment of thiol end groups, protected as thioacetyl moieties, was achieved. These serve as binding sites for adhesion to gold surfaces. In some cases, one end of the oligomeric chains is capped with a thiol group so that the surface attachments to gold could be studied. In other cases, thiol groups are affixed to both ends of the molecular chains so that future conduction studies could be done between proximal metallic probes. The rigid rod conjugated oligomers may act as molecular wires in molecular scale electronic devices, and they also serve as useful models for understanding analogous bulk polymers.

  DOI：

  10.1021/jo962336q