2,2'-((3-(2-bromoethoxy)-1,2-phenylene)bis(ethyne-2,1-diyl))bis((phenylethynyl)benzene) | 1380450-17-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,2'-((3-(2-bromoethoxy)-1,2-phenylene)bis(ethyne-2,1-diyl))bis((phenylethynyl)benzene)
• 英文别名: 1-(2-Bromoethoxy)-2,3-bis[2-[2-(2-phenylethynyl)phenyl]ethynyl]benzene；1-(2-bromoethoxy)-2,3-bis[2-[2-(2-phenylethynyl)phenyl]ethynyl]benzene
• CAS: 1380450-17-8
• 化学式: C₄₀H₂₅BrO
• 分子量: 601.542
• InChiKey: OJDZSTHVCTUOMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2'-((3-(2-bromoethoxy)-1,2-phenylene)bis(ethyne-2,1-diyl))bis((phenylethynyl)benzene) 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以99%的产率得到2,2'-((3-(2-iodoethoxy)-1,2-phenylene)bis(ethyne-2,1-diyl))bis((phenylethynyl)benzene)
  参考文献：
  名称：

  Polyaromatic Ribbons from Oligo-Alkynes via Selective Radical Cascade: Stitching Aromatic Rings with Polyacetylene Bridges

  摘要：

  Selective radical generation in conjugated oligomeric o-aryleneethynylenes initiates an intramolecular cascade which involves five fast radical cyclizations followed by aromatization via a 1,5-H shift with a >93% yield per step. This radical cascade transformation opens a new avenue for the systematic and controlled preparation of functionalized graphene nanoribbons where, potentially, each of the peripheral aromatic rings can be different.

  DOI：

  10.1021/ja3023626
• 作为产物：
  描述：

  O-3-iodophenyl N,N-diethylcarbamate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 18-冠醚-6 、 potassium carbonate 、 三乙胺 、 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 丙酮 为溶剂， 反应 33.0h， 生成 2,2'-((3-(2-bromoethoxy)-1,2-phenylene)bis(ethyne-2,1-diyl))bis((phenylethynyl)benzene)
  参考文献：
  名称：

  Polyaromatic Ribbons from Oligo-Alkynes via Selective Radical Cascade: Stitching Aromatic Rings with Polyacetylene Bridges

  摘要：

  Selective radical generation in conjugated oligomeric o-aryleneethynylenes initiates an intramolecular cascade which involves five fast radical cyclizations followed by aromatization via a 1,5-H shift with a >93% yield per step. This radical cascade transformation opens a new avenue for the systematic and controlled preparation of functionalized graphene nanoribbons where, potentially, each of the peripheral aromatic rings can be different.

  DOI：

  10.1021/ja3023626

文献信息

• Modular Synthesis of Graphene Nanoribbons And Graphene Substructures From Oligo-Alkynes
  申请人：The Florida State University Research Foundation,

  公开号：US20130109855A1

  公开（公告）日：2013-05-02

  A method for the synthesis of carbon-based structures, particularly graphene substructures and ribbons, from oligo- and poly-alkyne starting materials.

  一种用寡烯和多烯起始材料合成碳基结构的方法，特别是石墨烯亚结构和带状结构。
• MODULAR SYNTHESIS OF GRAPHENE NANORIBBONS AND GRAPHENE SUBSTRUCTURES FROM OLIGO-ALKYNES
  申请人：The Florida State University Research Foundation, Inc.

  公开号：US20150073145A1

  公开（公告）日：2015-03-12

  A method for the synthesis of carbon-based structures, particularly graphene substructures and ribbons, from oligo- and poly-alkyne starting materials.

  一种从寡聚和聚炔起始材料合成碳基结构，尤其是石墨烯亚结构和带状物的方法。
• US8927778B2
  申请人：——

  公开号：US8927778B2

  公开（公告）日：2015-01-06
• US9273023B2
  申请人：——

  公开号：US9273023B2

  公开（公告）日：2016-03-01
• Polyaromatic Ribbons from Oligo-Alkynes via Selective Radical Cascade: Stitching Aromatic Rings with Polyacetylene Bridges
  作者：Philip M. Byers、Igor V. Alabugin

  DOI：10.1021/ja3023626

  日期：2012.6.13

  Selective radical generation in conjugated oligomeric o-aryleneethynylenes initiates an intramolecular cascade which involves five fast radical cyclizations followed by aromatization via a 1,5-H shift with a >93% yield per step. This radical cascade transformation opens a new avenue for the systematic and controlled preparation of functionalized graphene nanoribbons where, potentially, each of the peripheral aromatic rings can be different.