2,11-dibromo-3,6,7,10-tetrakis(hexyloxy)triphenylene | 393171-12-5

• 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: 2,11-dibromo-3,6,7,10-tetrakis(hexyloxy)triphenylene
• 英文别名: 3,6-dibromo-2,7,10,11-tetrakis(hexyloxy)triphenylene；2,11-dibromo-3,6,7,10-tetrahexoxytriphenylene
• CAS: 393171-12-5
• 化学式: C₄₂H₅₈Br₂O₄
• 分子量: 786.728
• InChiKey: KMBDPKUJCMGPGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  778.8±55.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.51
• 重原子数：
  48.0
• 可旋转键数：
  24.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,11-dibromo-3,6,7,10-tetrakis(hexyloxy)triphenylene 在 copper(l) iodide 、 bis(triphenylphosphine)palladium(II) dichloride 、 三乙胺 作用下， 反应 21.66h， 生成 2,7,10,11-tetrakis(hexyloxy)-3-(trimethylsilylethynyl)-6-(3-methyl-3-hydroxybutynyl)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：

  苯,1,2-二溴-4,5-二(己氧基)- 在 溴 、 三氯化铁 、 sodium carbonate 、 三苯基膦 、 palladium dichloride 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 26.5h， 生成 2,11-dibromo-3,6,7,10-tetrakis(hexyloxy)triphenylene
  参考文献：
  名称：

  摘要：

  A series of novel triphenylenes has been synthesised by a combination of palladium catalysed coupling, oxidative cyclisation, bromination and nucleophilic aromatic substitution. The new derivatives are designed to have structures which are intermediate between the known symmetrical materials hexakis( hexyloxy) triphenylene and hexakis( hexylthio) triphenylene. The compounds having four hexyloxy and two hexylthio substituents form only Col(h) mesophases. Triphenylenes having four hexylthio and two hexyloxy substituents also give Col(h) mesophases but 3,6- bis(hexyloxy)-2,7,10,11-tetrakis(hexylthio) triphenylene 5 is unique in that it cools into a stable, more ordered phase. The low temperature phase, which appears to be indefinitely stable at ambient temperature, is assumed to be helical based on transition enthalpy data.

  DOI：

  10.1039/b103450m

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。
• Probing the structural factors influencing columnar mesophase formation and stability in triphenylene discotics
  作者：Andrew N. Cammidge、Céline Chausson、Hemant Gopee、Juanjuan Li、David L. Hughes

  DOI：10.1039/b913678a

  日期：——

  Series of structurally related substituted triphenylene derivatives were designed and synthesised to interrogate key features which determine mesophase formation and stability, and to challenge the general conclusions previously proposed by us and others. It is apparent that no single, simple principle can be universally applied.

  设计并合成了一系列结构相关的替代三苯基衍生物，以探讨决定介相形成和稳定性的关键特征，并挑战我们和其他人之前提出的一般结论。显然，没有单一的简单原则可以普遍适用。
• Expanded Porphyrin-like Structures Based on Twinned Triphenylenes
  作者：Hemant Gopee、Xiangfei Kong、Zhiqun He、Isabelle Chambrier、David L. Hughes、Graham J. Tizzard、Simon J. Coles、Andrew N. Cammidge

  DOI：10.1021/jo401551c

  日期：2013.9.20

  Triphenylene twins are intriguing structures, and those bridged through their 3,6-positions by dipyrromethene units give a new class of macrocycles that can be viewed as rigid, expanded porphyrin derivatives in which coplanarity is enforced in a formally antiaromatic π system. Somewhat surprisingly, however, macrocyclization leads to significant overall stabilization of the dipyrromethene chromophores

  三亚苯基双胞胎是令人着迷的结构，那些通过二吡咯亚甲基单元通过其3,6-位桥接的结构提供了一类新的大环，这些大环可以看作是刚性的，扩展的卟啉衍生物，其中在正式的抗芳构π系统中共面性得以增强。然而，令人惊讶的是，大环化导致二吡咯亚甲基生色团的显着整体稳定。
• Mixed Alkyl-Alkoxy Triphenylenes
  作者：Andrew N Cammidge、Hemant Gopee

  DOI：10.1080/714965603

  日期：2003.1