1,3,5-tris(1,12-dicarba-closo-dodecaboran-1-yl)benzene | 189301-08-4

• 英文名称: 1,3,5-tris(1,12-dicarba-closo-dodecaboran-1-yl)benzene
• CAS: 189301-08-4
• 化学式: C₁₂H₃₆B₃₀
• 分子量: 504.748
• InChiKey: WJZSCHBQWWHYGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  1,3,5-tris(1,12-dicarba-closo-dodecaboran-1-yl)benzene 、 (3-(ethylthio)propyl)dimethylsilyl chloride 在 t-BuLi 作用下， 以 乙醚 、 正戊烷 为溶剂， 以28%的产率得到1,3,5-tris[12-((3-(ethylthio)propyl)dimethylsilyl)-1,12-dicarba-closo-dodecaboran-1-yl]benzene
  参考文献：
  名称：

  Toward a Hexagonal Grid Polymer:  Synthesis, Coupling, and Chemically Reversible Surface-Pinning of the Star Connectors, 1,3,5-C₆H₃(CB₁₀H₁₀CX)₃

  摘要：

  A synthetic approach to a two-dimensional grid polymer is proposed and the execution of initial steps is described. Pd-catalyzed coupling of (1,12-dicarba-closo-dodecaboran-1-yl)copper (10) with iodobenzene, m-diiodobenzene, and 1,3,5-triiodobenzene yielded the known 1,12-dicarba-closo-dodecaboran-1-ylbenzene (3) and the new m-bis(1,12-dicarba-closo-dodecaboran-1-y (4) and 1,3,5-tris(1,12-dicarba-closo-dodecaboran-1-yl)benzene (1), yl)benzene (1), respectively. Each arm of the trigonal connector 1 was provided with one or two sticky tentacles by conversion to 1,3,5-tris[12-((3-(ethylthio)propyl)dimetylsilyl)-1,12-dicarba-closo-dodecarboran-1-yl]benzene (7) and 1,3,5-tris[12-(bis(3-(ethylthio)propyl)methylsilyl)-1,12-dicarba-closo-dodecarboran-1-yl]benzene (8). Linear coupling of carboranyl CH terminals through a mercury atom produced very stable dimeric structures from 3 and 4. The carborane 3, its mercury-linked dimer 13, the 1:1 complex of 13 with 2,2'-bipyridyl, and the 2:1 complex of 13 with 2,2'-bipyrimidyl have been structurally characterized by single-crystal X-ray crystallography, but crystals of 1 showed an intriguing disorder and could not be used for molecular structure determination. Grazing incidence IR spectra show that the tentacled species 7 and 8 adsorb firmly on the surface of gold, apparently without a strong preference for a particular orientation. At room temperature, the tritentacled species 7 can be removed readily and the hexatentacled species 8 more slowly by treatment with a THF solution containing fluoride, which severs the tentacles.

  DOI：

  10.1021/ja963331d
• 作为产物：
  描述：

  1,3,5-tris[12-((3-(ethylthio)propyl)dimethylsilyl)-1,12-dicarba-closo-dodecaboran-1-yl]benzene 在 tetra-n-butylamonium fluoride 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到1,3,5-tris(1,12-dicarba-closo-dodecaboran-1-yl)benzene
  参考文献：
  名称：

  Toward a Hexagonal Grid Polymer:  Synthesis, Coupling, and Chemically Reversible Surface-Pinning of the Star Connectors, 1,3,5-C₆H₃(CB₁₀H₁₀CX)₃

  摘要：

  A synthetic approach to a two-dimensional grid polymer is proposed and the execution of initial steps is described. Pd-catalyzed coupling of (1,12-dicarba-closo-dodecaboran-1-yl)copper (10) with iodobenzene, m-diiodobenzene, and 1,3,5-triiodobenzene yielded the known 1,12-dicarba-closo-dodecaboran-1-ylbenzene (3) and the new m-bis(1,12-dicarba-closo-dodecaboran-1-y (4) and 1,3,5-tris(1,12-dicarba-closo-dodecaboran-1-yl)benzene (1), yl)benzene (1), respectively. Each arm of the trigonal connector 1 was provided with one or two sticky tentacles by conversion to 1,3,5-tris[12-((3-(ethylthio)propyl)dimetylsilyl)-1,12-dicarba-closo-dodecarboran-1-yl]benzene (7) and 1,3,5-tris[12-(bis(3-(ethylthio)propyl)methylsilyl)-1,12-dicarba-closo-dodecarboran-1-yl]benzene (8). Linear coupling of carboranyl CH terminals through a mercury atom produced very stable dimeric structures from 3 and 4. The carborane 3, its mercury-linked dimer 13, the 1:1 complex of 13 with 2,2'-bipyridyl, and the 2:1 complex of 13 with 2,2'-bipyrimidyl have been structurally characterized by single-crystal X-ray crystallography, but crystals of 1 showed an intriguing disorder and could not be used for molecular structure determination. Grazing incidence IR spectra show that the tentacled species 7 and 8 adsorb firmly on the surface of gold, apparently without a strong preference for a particular orientation. At room temperature, the tritentacled species 7 can be removed readily and the hexatentacled species 8 more slowly by treatment with a THF solution containing fluoride, which severs the tentacles.

  DOI：

  10.1021/ja963331d