9,10-bis(4-(tris(4-bromophenyl)methyl)phenylethynyl) triptycene-d₈ | 1613248-98-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-bis(4-(tris(4-bromophenyl)methyl)phenylethynyl) triptycene-d₈
• 英文别名: 3,4,5,6,10,11,12,13-Octadeuterio-1,8-bis[2-[4-[tris(4-bromophenyl)methyl]phenyl]ethynyl]pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene；3,4,5,6,10,11,12,13-octadeuterio-1,8-bis[2-[4-[tris(4-bromophenyl)methyl]phenyl]ethynyl]pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene
• CAS: 1613248-98-8
• 化学式: C₇₄H₄₄Br₆
• 分子量: 1420.52
• InChiKey: IGZNQKNWZZOPFH-LREQGHIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.2
• 重原子数：
  80
• 可旋转键数：
  12
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  tritylacetylene 、 9,10-bis(4-(tris(4-bromophenyl)methyl)phenylethynyl) triptycene-d₈ 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到9,10-bis(4-(tris(4-(triphenylpropynyl)phenyl)methyl))phenylethynyl triptycene-d₈
  参考文献：
  名称：

  Rotation of a Bulky Triptycene in the Solid State: Toward Engineered Nanoscale Artificial Molecular Machines

  摘要：

  We report the design and dynamics of a solid-state molecular rotor with a large triptycene rotator. With a cross-section and surface area that are 2 and 3 times larger than those of the phenylene rotators previously studied in the solid state, it is expected that van der Waals forces and steric hindrance will render the motion of the larger triptycene more difficult. To address this challenge, we used a rigid and shape-persistent stator in a dendritic structure that reaches ca. 3.6 nm in length. Using variable-temperature solid-state (2)H NMR spectroscopy, we determined a symmetric three-fold rotational potential with a barrier of 10.2 kcal/mol and a pre-exponential factor of 1.1 × 10(10) s(-1), which correspond to ca. 4600 Brownian jumps per second in the solid state at 300 K.

  DOI：

  10.1021/ja503467e
• 作为产物：
  描述：

  tris(4-bromophenyl)-4-iodophenyl methane 、 9,10-diethynyltriptycene-d₈ 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以43%的产率得到9,10-bis(4-(tris(4-bromophenyl)methyl)phenylethynyl) triptycene-d₈
  参考文献：
  名称：

  Rotation of a Bulky Triptycene in the Solid State: Toward Engineered Nanoscale Artificial Molecular Machines

  摘要：

  We report the design and dynamics of a solid-state molecular rotor with a large triptycene rotator. With a cross-section and surface area that are 2 and 3 times larger than those of the phenylene rotators previously studied in the solid state, it is expected that van der Waals forces and steric hindrance will render the motion of the larger triptycene more difficult. To address this challenge, we used a rigid and shape-persistent stator in a dendritic structure that reaches ca. 3.6 nm in length. Using variable-temperature solid-state (2)H NMR spectroscopy, we determined a symmetric three-fold rotational potential with a barrier of 10.2 kcal/mol and a pre-exponential factor of 1.1 × 10(10) s(-1), which correspond to ca. 4600 Brownian jumps per second in the solid state at 300 K.

  DOI：

  10.1021/ja503467e

文献信息

• Rotation of a Bulky Triptycene in the Solid State: Toward Engineered Nanoscale Artificial Molecular Machines
  作者：Xing Jiang、Braulio Rodríguez-Molina、Narega Nazarian、Miguel A. Garcia-Garibay

  DOI：10.1021/ja503467e

  日期：2014.6.25

  We report the design and dynamics of a solid-state molecular rotor with a large triptycene rotator. With a cross-section and surface area that are 2 and 3 times larger than those of the phenylene rotators previously studied in the solid state, it is expected that van der Waals forces and steric hindrance will render the motion of the larger triptycene more difficult. To address this challenge, we used a rigid and shape-persistent stator in a dendritic structure that reaches ca. 3.6 nm in length. Using variable-temperature solid-state (2)H NMR spectroscopy, we determined a symmetric three-fold rotational potential with a barrier of 10.2 kcal/mol and a pre-exponential factor of 1.1 × 10(10) s(-1), which correspond to ca. 4600 Brownian jumps per second in the solid state at 300 K.