2-methoxy-3,6,7,10,11-penta(hexyloxy)triphenylene | 162281-26-7

• 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-methoxy-3,6,7,10,11-penta(hexyloxy)triphenylene
• 英文别名: 2,3,6,7,10-Pentahexoxy-11-methoxytriphenylene；2,3,6,7,10-pentahexoxy-11-methoxytriphenylene
• CAS: 162281-26-7
• 化学式: C₄₉H₇₄O₆
• 分子量: 759.123
• InChiKey: HIBINEDNJKKYSI-UHFFFAOYSA-N

物化性质

• 沸点：
  801.4±60.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.4
• 重原子数：
  55
• 可旋转键数：
  31
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-methoxy-3,6,7,10,11-penta(hexyloxy)triphenylene 在 氯代叔丁烷 、 lithium 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 2-(methylcarbamoylmethoxy)-3,6,7,10,11-penta(hexyloxy)triphenylene
  参考文献：
  名称：

  Synthesis and Mesomorphism of Asymmetric Triphenylene Discotic Liquid Crystals Bearing with Mono-Amido-Based Alkyl Soft Chains

  摘要：

  A series of triphenylene discotic liquid crystals with amido-based alkyl chains in different lengths were synthesized and characterized. The liquid crystal properties were studied with differential scanning calorimetry and polarizing optical microscopy. The influences of amide alkyl chain lengths on the mesomorphism were discussed. Based on the results, we concluded that the triphenylene discogens with an amido-based alkyl chain could form intermolecular hydrogen bonds inside their columnar stacks, and hence, exhibit higher melting and clearing points, and wider mesophase ranges.

  DOI：

  10.1080/15421406.2011.569516
• 作为产物：
  描述：

  1,2-二己氧基苯 在 iron(III) chloride 、 硫酸 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 2-methoxy-3,6,7,10,11-penta(hexyloxy)triphenylene
  参考文献：
  名称：

  Synthesis and Mesomorphism of Asymmetric Triphenylene Discotic Liquid Crystals Bearing with Mono-Amido-Based Alkyl Soft Chains

  摘要：

  A series of triphenylene discotic liquid crystals with amido-based alkyl chains in different lengths were synthesized and characterized. The liquid crystal properties were studied with differential scanning calorimetry and polarizing optical microscopy. The influences of amide alkyl chain lengths on the mesomorphism were discussed. Based on the results, we concluded that the triphenylene discogens with an amido-based alkyl chain could form intermolecular hydrogen bonds inside their columnar stacks, and hence, exhibit higher melting and clearing points, and wider mesophase ranges.

  DOI：

  10.1080/15421406.2011.569516

文献信息

• Convenient synthesis of a discotic side group liquid crystal polymer
  作者：David Stewart、Gillian S. Mchattie、Corrie T. Imrie

  DOI：10.1039/a705378i

  日期：——

  The synthesis of a discotic side group liquid crystal polymer based on poly(methyl methacrylate) is reported. This involves the oxidative coupling of 3,3′,4,4′-tetrakis(hexyloxy)biphenyl with 1-hexyloxy-2-methoxybenzene to yield the unsymmetrical triphenylene nucleus, 2-methoxy-3,6,7,10,11-pentakis(hexyloxy)triphenylene. Subsequent demethylation followed by reactions first with 1,11-dibromoundecane and then with the potassium salt of methacrylic acid yielded the polymerisable monomer, 11-[3,6,7,10,11-pentakis(hexyloxy)-2-oxytriphenylene]undecyl methacrylate. This was polymerised in benzene using azoisobutyronitrile as the initiator. The thermal properties of the resulting polymer are described.

  报道了一种基于聚（甲基丙烯酸甲酯）的盘状侧基液晶聚合物的合成。这涉及到3,3′,4,4′-四己氧基联苯与1-己氧基-2-甲氧基苯的氧化偶联，生成不对称的三苯烯核2-甲氧基-3,6,7,10,11-五己氧基三苯烯。随后的去甲基化反应，先与1,11-二溴十一烷反应，再与丙烯酸钾盐反应，得到可聚合的单体11-[3,6,7,10,11-五己氧基-2-氧三苯烯]十一烷基甲基丙烯酸酯。该单体在苯中以偶氮异丁腈作为引发剂进行聚合。文中描述了所得聚合物的热性能。
• Discogens Possessing Aryl Side Groups Synthesized by Suzuki Coupling of Triphenylene Triflates and Their Self-Organization Behavior
  作者：Ke-Qing Zhao、Yue Gao、Wen-Hao Yu、Ping Hu、Bi-Qin Wang、Benoît Heinrich、Bertrand Donnio

  DOI：10.1002/ejoc.201600270

  日期：2016.6

  triphenylene triflate precursors by Suzuki coupling reactions with various commercial arylboronic acids (e.g., aryl = phenylene, thiophene, naphthalene, triarylamine, carbazole, and fluorene). The synthesized discogens display broad mesophase ranges and high thermal stabilities. Moreover, those bearing triarylamine, carbazole, and fluorene side groups are also blue-light emitters. The availability of the triflate

  Pd催化的芳基硼酸和溴芳烃之间的Suzuki交叉偶联反应已广泛应用于液晶材料的合成。然而，尽管芳基三氟甲磺酸酯衍生物具有较高的化学耐受性、反应性和化学可及性，但其使用较少。在本报告中，通过 Suzuki 与各种商业芳基硼酸（例如，芳基 = 亚苯基、噻吩、萘、三芳基胺、咔唑和芴）的偶联反应，从适当的三氟甲磺酸三苯联苯前体以良好的产率合成了三个系列的圆盘基。合成的圆盘基显示出广泛的中间相范围和高热稳定性。此外，带有三芳胺、咔唑和芴侧基的那些也是蓝光发射体。
• [EN] SYNTHESIS OF SUBSTITUTED TRIPHENYLENES, USEFUL AS DISCOTIC LIQUID CRYSTALS<br/>[FR] SYNTHESE DE TRIPHENILENES SUBSTITUES UTILES POUR LES CRISTAUX LIQUIDES EN FORME DE DISQUE
  申请人：BRITISH TECHNOLOGY GROUP LIMITED

  公开号：WO1994029243A1

  公开（公告）日：1994-12-22

  (EN) Unsymmetrically substituted triphenylenes required in the synthesis of polymeric discotic liquid crystals are made using iron (III) chloride in organic solvent at room temperature to effect the oxidative coupling of 1,2-dialkoxybenzenes to 3,3',4,4'-tetraalkoxybiphenyls. This is followed by a reductive workup. The same oxidation-reduction protocol also proves effective in the trimerisation of 1,2-dialkoxybenzenes.(FR) Les triphénylènes à substitution asymétrique nécessaires à la synthèse des cristaux liquides (en disque) sont obtenus en utilisant du chlorure de fer (III), contenu dans un solvant organique à température ambiante, pour réaliser la liaison oxydante de 1,2-dialkoxybenzènes et de 3,3',4,4'-tétra-alkoxybiphényles. Ceci est suivi d'un bilan réducteur. Le même protocole d'oxydo-réduction a prouvé son efficacité dans la trimérisation des 1,2-dialkoxybenzènes.
• Synthesis and Mesomorphism of Asymmetric Triphenylene Discotic Liquid Crystals Bearing with Mono-Amido-Based Alkyl Soft Chains
  作者：K. Q. Zhao、J. Z. Guo、W. H. Yu、L. Wang、P. Hu、B. Q. Wang、H. Monobe、Y. Shimizu

  DOI：10.1080/15421406.2011.569516

  日期：2011.6.30

  A series of triphenylene discotic liquid crystals with amido-based alkyl chains in different lengths were synthesized and characterized. The liquid crystal properties were studied with differential scanning calorimetry and polarizing optical microscopy. The influences of amide alkyl chain lengths on the mesomorphism were discussed. Based on the results, we concluded that the triphenylene discogens with an amido-based alkyl chain could form intermolecular hydrogen bonds inside their columnar stacks, and hence, exhibit higher melting and clearing points, and wider mesophase ranges.