2,7-dimethoxy-3,6,10,11-tetrakis(hexyloxy)triphenylene | 155787-81-8

• 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: 2,7-dimethoxy-3,6,10,11-tetrakis(hexyloxy)triphenylene
• 英文别名: 2,7-bis(methyloxy)-3,6,10,11-tetrakis(hexyloxy)triphenylene；2,3,7,10-Tetrahexoxy-6,11-dimethoxytriphenylene
• CAS: 155787-81-8
• 化学式: C₄₄H₆₄O₆
• 分子量: 688.989
• InChiKey: OUCLDWWNKCMEFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14
• 重原子数：
  50
• 可旋转键数：
  26
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  2,7-dimethoxy-3,6,10,11-tetrakis(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 26.0h， 生成 2,7-di(methylaminocarbonylmethyloxy)-3,6,10,11-tetrakis(hexyloxy)triphenylene
  参考文献：
  名称：

  Synthesis of Amide Group Containing Triphenylene Derivatives as Discotic Liquid Crystals and Organic Gelators

  摘要：

  Intermolecular hydrogen bond is an efficient way to anchor columnar assembly of discotic liquid crystals, and would result in more ordered columnar mesphase and faster charged carrier mobility. In this report, a series of peripheral functionalized triphenylene derivatives, C18H6(OC6H13)(4)(OCH2CONHR)(2), which contains amide groups at the 2,7-positions, have been synthesized. The polarized optical microscopy (POM) and differential scanning calorimetry (DSC) results showed that these compounds exhibit hexagonal columnar mesophases. The triphenylene derivatives gelate in the solution of octane, petroleum ether, cyclohexane and p-xylene and form stable organic gels. The xerogels formed from organic solvents were analyzed by scanning electron microscope (SEM) and showed fiber-like or sponge-like morphology. It is demonstrated that intermolecular hydrogen bonds stabilize the columnar molecular organization and assembly in mesomorphic state and organic gel.

  DOI：

  10.1080/15421400903112069
• 作为产物：
  描述：

  4-bromo-2-hexyloxy-1-methoxybenzene 在 iron(III) chloride 、 硫酸 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 2,7-dimethoxy-3,6,10,11-tetrakis(hexyloxy)triphenylene
  参考文献：
  名称：

  苯三氟甲磺酸的铃木偶联合成的具有芳基侧基的 Discogens 及其自组织行为

  摘要：

  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。

  DOI：

  10.1002/ejoc.201600270

文献信息

• A quick-and-easy route to unsymmetrically substituted derivatives of triphenylene: preparation of polymeric discotic liquid crystals
  作者：Neville Boden、Richard J. Bushby、Andrew N. Cammidge

  DOI：10.1039/c39940000465

  日期：——

  Unsymmetrically substituted triphenylenes can be obtained by the iron(III) chloride mediated oxidative coupling of a 3,3′,4,4′-tetraalkoxybiphenyl with a 1,2-dialkoxybenzene thus opening up a practicable route to polymeric discotic liquid crystals.

  通过氯化铁（III）介导的 3,3′,4,4′-四烷氧基联苯与 1,2-二烷氧基苯的氧化偶联，可以获得不对称取代的三苯乙烯，从而为聚合盘状液晶开辟了一条可行的途径。
• Boden, Neville; Bushby, Richard J.; Cammidge, Andrew N., Journal of the American Chemical Society, 1995, vol. 117, # 3, p. 924 - 926
  作者：Boden, Neville、Bushby, Richard J.、Cammidge, Andrew N.

  DOI：——

  日期：——
• [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.
• 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。
• Synthesis of Amide Group Containing Triphenylene Derivatives as Discotic Liquid Crystals and Organic Gelators
  作者：Y. F. Bai、K. Q. Zhao、P. Hu、B. Q. Wang、Y. Shimizu

  DOI：10.1080/15421400903112069

  日期：2009.9.3

  Intermolecular hydrogen bond is an efficient way to anchor columnar assembly of discotic liquid crystals, and would result in more ordered columnar mesphase and faster charged carrier mobility. In this report, a series of peripheral functionalized triphenylene derivatives, C18H6(OC6H13)(4)(OCH2CONHR)(2), which contains amide groups at the 2,7-positions, have been synthesized. The polarized optical microscopy (POM) and differential scanning calorimetry (DSC) results showed that these compounds exhibit hexagonal columnar mesophases. The triphenylene derivatives gelate in the solution of octane, petroleum ether, cyclohexane and p-xylene and form stable organic gels. The xerogels formed from organic solvents were analyzed by scanning electron microscope (SEM) and showed fiber-like or sponge-like morphology. It is demonstrated that intermolecular hydrogen bonds stabilize the columnar molecular organization and assembly in mesomorphic state and organic gel.