tert-butyl [2-iodo-5-(2-(benzyloxy)carbonylaminoethoxy)phenoxy]acetate | 1004321-27-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl [2-iodo-5-(2-(benzyloxy)carbonylaminoethoxy)phenoxy]acetate
• CAS: 1004321-27-0
• 化学式: C₂₂H₂₆INO₆
• 分子量: 527.356
• InChiKey: TWZVIUIUZPOFNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.09
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl [2-iodo-5-(2-(benzyloxy)carbonylaminoethoxy)phenoxy]acetate 、 频那醇硼烷 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以87%的产率得到tert-butyl [5-(2-(benzyloxy)carbonylaminoethoxy)-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenoxy]acetate
  参考文献：
  名称：

  Zipper Assembly of Photoactive Rigid-Rod Naphthalenediimide π-Stack Architectures on Gold Nanoparticles and Gold Electrodes

  摘要：

  We introduce zipper assembly as a simple and general concept to create complex functional architectures an conducting surfaces. Rigid-rod pi-stack architecture composed of p-oligophenyl rods and blue naphthalenediimide (NDI) stacks is selected as an example. First, short p-quaterphenyl initiators with four anionic NDIs are deposited on gold. Then, long p-octiphenyl propagators with eight cationic NDIs are added. The lower half of the propagator pi-stacks with the initiator, whereas the upper half of the molecule remains free. These cationic sticky-ends zip up with anionic propagators to produce anionic sticky-ends, and so on. Zipper assembly on gold nanoparticles is demonstrated by the appearance of the absorption of face-to-face NDI pi-stacks and the shift of the surface plasmon resonance band with increasing layer thickness. Complete inhibition by zipper capping demonstrates that zipper assembly affords complex architectures that are more ordered than those obtained by conventional layer-by-layer (LBL) approaches. Zipper assembly on gold electrodes produces increasing photocurrents with increasing number of zipped layers. The photocurrents obtained by this method are much higher than those obtained by conventional LBL controls; zipper termination by capping cleanly stops any increase in photocurrent.

  DOI：

  10.1021/ja077099v
• 作为产物：
  描述：

  2-碘-5-(2-(苄氧基)羰基氨基乙氧基)苯酚 、 溴乙酸叔丁酯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以83%的产率得到tert-butyl [2-iodo-5-(2-(benzyloxy)carbonylaminoethoxy)phenoxy]acetate
  参考文献：
  名称：

  Zipper Assembly of Photoactive Rigid-Rod Naphthalenediimide π-Stack Architectures on Gold Nanoparticles and Gold Electrodes

  摘要：

  We introduce zipper assembly as a simple and general concept to create complex functional architectures an conducting surfaces. Rigid-rod pi-stack architecture composed of p-oligophenyl rods and blue naphthalenediimide (NDI) stacks is selected as an example. First, short p-quaterphenyl initiators with four anionic NDIs are deposited on gold. Then, long p-octiphenyl propagators with eight cationic NDIs are added. The lower half of the propagator pi-stacks with the initiator, whereas the upper half of the molecule remains free. These cationic sticky-ends zip up with anionic propagators to produce anionic sticky-ends, and so on. Zipper assembly on gold nanoparticles is demonstrated by the appearance of the absorption of face-to-face NDI pi-stacks and the shift of the surface plasmon resonance band with increasing layer thickness. Complete inhibition by zipper capping demonstrates that zipper assembly affords complex architectures that are more ordered than those obtained by conventional layer-by-layer (LBL) approaches. Zipper assembly on gold electrodes produces increasing photocurrents with increasing number of zipped layers. The photocurrents obtained by this method are much higher than those obtained by conventional LBL controls; zipper termination by capping cleanly stops any increase in photocurrent.

  DOI：

  10.1021/ja077099v