3,6-diethynyl-2,7,10,11-tetrakis(hexyloxy)triphenylene | 1236150-77-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3,6-diethynyl-2,7,10,11-tetrakis(hexyloxy)triphenylene
• 英文别名: 2,11-Diethynyl-3,6,7,10-tetrakis(hexyloxy)triphenylene；2,11-diethynyl-3,6,7,10-tetrahexoxytriphenylene
• CAS: 1236150-77-8
• 化学式: C₄₆H₆₀O₄
• 分子量: 676.98
• InChiKey: OQDKMIXBDHZFJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  50
• 可旋转键数：
  26
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-二碘噻吩 、 3,6-diethynyl-2,7,10,11-tetrakis(hexyloxy)triphenylene 在 bis(triphenylphosphine)palladium(II) dichloride 、 三乙胺 、 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以27%的产率得到2,7,10,11-tetrakis(hexyloxy)-3,6-bis[2-(5-iodothiophene-2-yl)ethynyl]triphenylene
  参考文献：
  名称：

  Discotic Triphenylene Twins Linked through Thiophene Bridges: Controlling Nematic Behavior in an Intriguing Class of Functional Organic Materials

  摘要：

  Substituted triphenylenes and similar discotic molecules have a strong tendency toward columnar organization. Nematic mesophases are much less commonly observed in discotic systems. We have demonstrated a general strategy whereby discotic triphenylenes can be twinned to form stable, boardlike materials that display only nematic mesophases. The dominant structural feature that leads to nematic behavior is an enforced void region in the center of the macrocycle that results from bridging through the triphenylene 3,6-positions. This precludes simple columnar assembly because it would lead to free space through the center of each stack. Selection of appropriate bridging units allows materials to be designed which combine molecular features, such as the optoelectronic properties of electron-rich triphenylenes and conjugated thiophene units, with the processability, self-healing, and alignment features inherent in nematic mesophases. In addition, communication across twinned structures can lead to additional enhancement of optoelectronic behavior. This is particularly apparent in fully conjugated, planar twin 12 which is formally expected to have some antiaromatic character. This character is manifested in its spectral properties, and particularly noteworthy is its strong, Stokes shifted emission at around 500 nm

  DOI：

  10.1021/jo3002886
• 作为产物：
  描述：

  2,7,10,11-tetrakis(hexyloxy)-3,6-bis(3-methyl-3-hydroxybutynyl)triphenylene 在 sodium hydride 作用下， 以 甲苯 为溶剂， 以71%的产率得到3,6-diethynyl-2,7,10,11-tetrakis(hexyloxy)triphenylene
  参考文献：
  名称：

  Antiaromatic twinned triphenylene discotics showing nematic phases and 2-dimensional π-overlap in the solid state

  摘要：

  基于脱氢环烯核心、通过三苯并环位置相连而构建的正式反芳香性盘状双分子，具有引人注目的分子和超分子特性，与大多数盘状三苯并环烯及类似材料不同，这些双分子在加热时会形成向列相中间相。

  DOI：

  10.1039/c0cc00311e

文献信息

• Antiaromatic twinned triphenylene discotics showing nematic phases and 2-dimensional π-overlap in the solid state
  作者：Liang Zhang、Hemant Gopee、David L. Hughes、Andrew N. Cammidge

  DOI：10.1039/c0cc00311e

  日期：——

  Construction of formally antiaromatic discotic twins based on dehydroannulene cores linked through non-adjacent positions on triphenylenes gives stable molecules with intriguing molecular and supramolecular properties and, unlike the majority of discotic triphenylenes and similar materials, the twins form nematic mesophases on heating.

  基于脱氢环烯核心、通过三苯并环位置相连而构建的正式反芳香性盘状双分子，具有引人注目的分子和超分子特性，与大多数盘状三苯并环烯及类似材料不同，这些双分子在加热时会形成向列相中间相。
• Discotic Triphenylene Twins Linked through Thiophene Bridges: Controlling Nematic Behavior in an Intriguing Class of Functional Organic Materials
  作者：Liang Zhang、David L. Hughes、Andrew N. Cammidge

  DOI：10.1021/jo3002886

  日期：2012.5.4

  Substituted triphenylenes and similar discotic molecules have a strong tendency toward columnar organization. Nematic mesophases are much less commonly observed in discotic systems. We have demonstrated a general strategy whereby discotic triphenylenes can be twinned to form stable, boardlike materials that display only nematic mesophases. The dominant structural feature that leads to nematic behavior is an enforced void region in the center of the macrocycle that results from bridging through the triphenylene 3,6-positions. This precludes simple columnar assembly because it would lead to free space through the center of each stack. Selection of appropriate bridging units allows materials to be designed which combine molecular features, such as the optoelectronic properties of electron-rich triphenylenes and conjugated thiophene units, with the processability, self-healing, and alignment features inherent in nematic mesophases. In addition, communication across twinned structures can lead to additional enhancement of optoelectronic behavior. This is particularly apparent in fully conjugated, planar twin 12 which is formally expected to have some antiaromatic character. This character is manifested in its spectral properties, and particularly noteworthy is its strong, Stokes shifted emission at around 500 nm