β-bromo-3,6,7,10,11-pentakis(heptyloxy)triphenylene | 1260118-27-1

• 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: β-bromo-3,6,7,10,11-pentakis(heptyloxy)triphenylene
• 英文别名: 2-Bromo-3,6,7,10,11-pentaheptoxytriphenylene；2-bromo-3,6,7,10,11-pentaheptoxytriphenylene
• CAS: 1260118-27-1
• 化学式: C₅₃H₈₁BrO₅
• 分子量: 878.127
• InChiKey: DMBXAGJGLHDKLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.8
• 重原子数：
  59
• 可旋转键数：
  35
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  β-bromo-3,6,7,10,11-pentakis(heptyloxy)triphenylene 、 2-甲基-3-丁炔-2-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  π-Conjugated Triphenylene Twins Exhibiting Polymesomorphism Including the Nematic Phase

  摘要：

  Novel discotic liquid crystals possessing two triphenylene (TP) mesogenic cores covalently connected via a rigid spacer, i.e., -conjugated ethynyl- or butadiynyl-bridge, (TP twins) are reported. The TP twins are categorized by the lengths of -substituted chains (R2 and R3) and peripheral alkoxy or branched aliphatic chains (R1 and R4). Three varieties of TP twins are prepared: A) TP twins having identical -substituted and peripheral chains (R1=R2=R3=R4), B) equivalent TP entities having a -substituted chain (R2=R3) and peripheral chains (R1=R4) of different length from the substitution, and C) TP twins with different TP entities having the same -substituted and peripheral alkoxy chains (R1=R2, R3=R4). The phase behavior is characterized by differential scanning calorimetry (DSC), polarizing optical microscopy (POM) and X-ray diffraction (XRD) studies. These TP twins exhibit a discotic nematic (N) and/or columnar rectangular (Colr) mesophases over a wide temperature range. We found that the relative length of rigid spacer and -substituted alkoxy chains play an important role in the creation of the molecular self-assembly and formation of the mesophases. To the best of our knowledge, this is the first report of TP twins exhibiting polymesomorphism.

  DOI：

  10.1080/15421400902987677
• 作为产物：
  描述：

  1-Bromo-2-(heptyloxy)benzene 、 3,3',4,4'-tetrakis(heptyloxy)-1,1'-biphenyl 在 五氯化钼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 β-bromo-3,6,7,10,11-pentakis(heptyloxy)triphenylene
  参考文献：
  名称：

  π-Conjugated Triphenylene Twins Exhibiting Polymesomorphism Including the Nematic Phase

  摘要：

  Novel discotic liquid crystals possessing two triphenylene (TP) mesogenic cores covalently connected via a rigid spacer, i.e., -conjugated ethynyl- or butadiynyl-bridge, (TP twins) are reported. The TP twins are categorized by the lengths of -substituted chains (R2 and R3) and peripheral alkoxy or branched aliphatic chains (R1 and R4). Three varieties of TP twins are prepared: A) TP twins having identical -substituted and peripheral chains (R1=R2=R3=R4), B) equivalent TP entities having a -substituted chain (R2=R3) and peripheral chains (R1=R4) of different length from the substitution, and C) TP twins with different TP entities having the same -substituted and peripheral alkoxy chains (R1=R2, R3=R4). The phase behavior is characterized by differential scanning calorimetry (DSC), polarizing optical microscopy (POM) and X-ray diffraction (XRD) studies. These TP twins exhibit a discotic nematic (N) and/or columnar rectangular (Colr) mesophases over a wide temperature range. We found that the relative length of rigid spacer and -substituted alkoxy chains play an important role in the creation of the molecular self-assembly and formation of the mesophases. To the best of our knowledge, this is the first report of TP twins exhibiting polymesomorphism.

  DOI：

  10.1080/15421400902987677

文献信息

• Synthesis and Liquid-Crystalline Properties of β-Bromopentakis(Alkoxy) Triphenylene: Reactivity of VOCl₃, MoCl₅, and FeCl₃as Oxidants
  作者：Sanjay Kumar Varshney、Hiroki Nagayama、D. S. Shankar Rao、Hideo Takezoe

  DOI：10.1080/15421406.2010.504514

  日期：2010.10.14

  We present a simple synthetic strategy leading to nonsymmetrical functionalized hexasubstituted triphenylene. Further, new -bromopentakis(alkoxy)triphenylene was synthesized applying this strategy and reactivity of oxidizing agents such as VOCl3, MoCl5, and FeCl3 was investigated. The liquid-crystalline properties were studied by polarizing optical microscope (POM), differential scanning calorimetry (DSC), and X-ray diffraction (XRD) studies. The higher homologues exhibit a columnar hexagonal (Colh) phase, whereas lower homologues also exhibit a columnar hexagonal plastic (Colhp) phase. These mesophases are stable below and above the ambient temperature. We studied the effect of polar substitution on molecular self-assembly and found that a bromo bulky substituent at the -position of pentakis(alkoxy)triphenylenes stabilized the intra- or intermolecular interaction between the cores to form columnar mesophases.
• π-Conjugated Triphenylene Twins Exhibiting Polymesomorphism Including the Nematic Phase
  作者：Sanjay Kumar Varshney、Hideo Takezoe、Veena Prasad、D. S. Shankar Rao

  DOI：10.1080/15421400902987677

  日期：2009.12.7

  Novel discotic liquid crystals possessing two triphenylene (TP) mesogenic cores covalently connected via a rigid spacer, i.e., -conjugated ethynyl- or butadiynyl-bridge, (TP twins) are reported. The TP twins are categorized by the lengths of -substituted chains (R2 and R3) and peripheral alkoxy or branched aliphatic chains (R1 and R4). Three varieties of TP twins are prepared: A) TP twins having identical -substituted and peripheral chains (R1=R2=R3=R4), B) equivalent TP entities having a -substituted chain (R2=R3) and peripheral chains (R1=R4) of different length from the substitution, and C) TP twins with different TP entities having the same -substituted and peripheral alkoxy chains (R1=R2, R3=R4). The phase behavior is characterized by differential scanning calorimetry (DSC), polarizing optical microscopy (POM) and X-ray diffraction (XRD) studies. These TP twins exhibit a discotic nematic (N) and/or columnar rectangular (Colr) mesophases over a wide temperature range. We found that the relative length of rigid spacer and -substituted alkoxy chains play an important role in the creation of the molecular self-assembly and formation of the mesophases. To the best of our knowledge, this is the first report of TP twins exhibiting polymesomorphism.