2-Hydroxy-3-methoxy-6,7,10,11-tetrapentyloxytriphenylene | 168847-16-3

• 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-Hydroxy-3-methoxy-6,7,10,11-tetrapentyloxytriphenylene
• 英文别名: 2-hydroxy-3-methoxy-6,7,10,11-tetrakis-pentyloxy triphenylene；2-Triphenylenol, 3-methoxy-6,7,10,11-tetrakis(pentyloxy)-；3-methoxy-6,7,10,11-tetrapentoxytriphenylen-2-ol
• CAS: 168847-16-3
• 化学式: C₃₉H₅₄O₆
• 分子量: 618.854
• InChiKey: WFXWUHRPYKGVDG-UHFFFAOYSA-N

物化性质

• 沸点：
  733.2±55.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  45
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-3-methoxy-6,7,10,11-tetrapentyloxytriphenylene 在 4-二甲氨基吡啶 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 6-(3-Methoxy-6,7,10,11-tetrapentoxytriphenylen-2-yl)oxyhexyl 9,10-dioxoanthracene-2-carboxylate
  参考文献：
  名称：

  Synthesis of liquid crystalline anthraquinolyl–triphenylenes

  摘要：

  The synthesis, electrochemistry and mesogenic properties of novel anthraquinolyl-triphenylenes are described. H-1 NMR, UV-vis, solution electrochemistry and molecular modelling studies indicate that an intermolecular charge-transfer interaction occurs between the anthraquinone moiety and the triphenylene nucleus. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01370-8
• 作为产物：
  描述：

  1,2-bis(pentyloxy)benzene 在 iron(III) chloride 、 一氯化碘 、 铜 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 4.5h， 生成 2-Hydroxy-3-methoxy-6,7,10,11-tetrapentyloxytriphenylene
  参考文献：
  名称：

  The Synthesis and Mesophases Studies of a Novel Discotic Compound Containing Two Triphenylene Cores Linked by Crown Ether

  摘要：

  In this study, a novel discotic compound based on triphenylene core were synthesized. 6,7,10,11-tetrapentyloxy-2-hydroxy-3-methoxy triphenylene was synthesized via the common synthisis route including the Williamson Etherification of catechol, the iodination of 1,2-dipentyloxybenzene, the Ullman Coupling and the coupling of 3,3'-4,4'-tetrapentyloxy diphenyl and methoxy-phenol;Bis-(8-bromooctanoyl)-dibenzo-18-crown-6 was obtained from 8-bromooctanoic acid and dibenzo-18-crown-6 in polyphosphoric acid and then reacted in Et3SiH with trifluoroacetic acid as catalyst to obtain bis-(8-bromooctyl)-dibenzo-18-crown-6. Bis-(8-bromooctyl)-dibenzo-18-crown-6 reacted with 6,7,10,11-tetrapentyloxy-2-hydroxy-3-methoxy triphenylene via Williamson reaction to produce the goal product. The chemical structures of the compounds were identified by using fourier transform infrared spectroscopy, nuclear magnetic resonance and the thermal properties were characterized by optical polarizing microscope and differential scanning calorimeter.

  DOI：

  10.1080/15421406.2011.570129

文献信息

• Control of Stripelike and Hexagonal Self-Assembly of Gold Nanoparticles by the Tuning of Interactions between Triphenylene Ligands
  作者：Zhongrong Shen、Mami Yamada、Mikio Miyake

  DOI：10.1021/ja073518c

  日期：2007.11.1

  We describe the self-assembly of gold nanoparticles (Au NPs) protected with newly synthesized discotic liquid crystalline molecules of hexaalkoxy-substituted triphenylene (TP) in mixed toluene/methanol solvent. The stripelike (i.e., 2D consisting of linear 1D in stripe) self-assembly is realized successfully by the aid of pi-pi stacking of TP ligand on Au NPs. The smaller Au NPs with TP (AuTP) or the

  我们描述了在混合甲苯/甲醇溶剂中用新合成的六烷氧基取代的苯并苯 (TP) 的盘状液晶分子保护的金纳米粒子 (Au NPs) 的自组装。借助 TP 配体在 Au NPs 上的 pi-pi 堆叠，成功实现了条纹状（即由条纹中的线性一维组成的二维）自组装。具有 TP (AuTP) 的较小 Au NPs 或 TP 与金核之间较长的烷基链在 TP 部分之间提供更多的自由空间。这些空间允许在相邻的 AuTP 上轻松插入 TP 以导致粒子间 pi-pi 相互作用以形成条状排列。溶剂亲水性还可以作为一个受控指标来调整条纹状、六边形密堆积 (hcp) 或无序之间的排列。我们通过改变甲醇与甲苯的比例来改变溶剂的亲水性，这会影响 AuTP 溶液（在甲苯中）和沉积（在甲醇中）的平衡。TPs 之间较大的空间和适当的溶剂亲水性实现了由 TPs 之间强烈的 pi-pi 相互作用引起的条纹状自组装，这通过 TEM 以及荧光、动态光散射和
• Self-assembly of discotic liquid crystalline molecule-modified gold nanoparticles: control of 1D and hexagonal ordering induced by solvent polarity
  作者：Mami Yamada、Zhongrong Shen、Mikio Miyake

  DOI：10.1039/b604001b

  日期：——

  Gold nanoparticles fully coated with discotic liquid crystalline molecules of hexaalkoxy-substituted triphenylene (Au–TP) have been synthesised, the self-assembled structure of which could be controlled (hexagonal or 1D nanochain) just by altering the ratio of methanol to toluene in the solvent.

  我们合成了完全包覆有六烷氧基取代三亚苯（Au-TP）盘状液晶分子的金纳米粒子，只需改变溶剂中甲醇和甲苯的比例，就能控制其自组装结构（六角形或一维纳米链）。
• Bushby; Lu, Synthesis, 2001, # 5, p. 763 - 767
  作者：Bushby、Lu

  DOI：——

  日期：——
• Closs, Fritz; Haeubling, Lukas; Henderson, Philippe, Journal of the Chemical Society. Perkin transactions I, 1995, # 7, p. 829 - 838
  作者：Closs, Fritz、Haeubling, Lukas、Henderson, Philippe、Ringsdorf, Helmut、Schuhmacher, Peter

  DOI：——

  日期：——
• The Synthesis and Mesophases Studies of a Novel Discotic Compound Containing Two Triphenylene Cores Linked by Crown Ether
  作者：Chunxiu Zhang、Jialing Pu、Hao Wu、Shudan Cheng、Rui Zhang、A. Zhagn、Mingxia Zhang

  DOI：10.1080/15421406.2011.570129

  日期：2011.6.30

  In this study, a novel discotic compound based on triphenylene core were synthesized. 6,7,10,11-tetrapentyloxy-2-hydroxy-3-methoxy triphenylene was synthesized via the common synthisis route including the Williamson Etherification of catechol, the iodination of 1,2-dipentyloxybenzene, the Ullman Coupling and the coupling of 3,3'-4,4'-tetrapentyloxy diphenyl and methoxy-phenol;Bis-(8-bromooctanoyl)-dibenzo-18-crown-6 was obtained from 8-bromooctanoic acid and dibenzo-18-crown-6 in polyphosphoric acid and then reacted in Et3SiH with trifluoroacetic acid as catalyst to obtain bis-(8-bromooctyl)-dibenzo-18-crown-6. Bis-(8-bromooctyl)-dibenzo-18-crown-6 reacted with 6,7,10,11-tetrapentyloxy-2-hydroxy-3-methoxy triphenylene via Williamson reaction to produce the goal product. The chemical structures of the compounds were identified by using fourier transform infrared spectroscopy, nuclear magnetic resonance and the thermal properties were characterized by optical polarizing microscope and differential scanning calorimeter.