2,3,6,7,10,11-Hexakis(nonyloxy)triphenylene | 70351-88-1

• 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: 2,3,6,7,10,11-Hexakis(nonyloxy)triphenylene
• 英文别名: 2,3,6,7,10,11-hexa(nonoxy)triphenylene
• CAS: 70351-88-1
• 化学式: C₇₂H₁₂₀O₆
• 分子量: 1081.74
• InChiKey: XWRRXWLNNCUCSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  28.5
• 重原子数：
  78
• 可旋转键数：
  54
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  2,3,6,7,10,11-Hexakis(nonyloxy)triphenylene 在 硝酸 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 生成 1-Nitro-2,3,6,7,10,11-hexakis-nonyloxy-triphenylene
  参考文献：
  名称：

  摘要：

  This paper reports on synthesis and investigation of columnar mesophases of the new members of the homologous series of nitro and amino derivatives of hexaalkoxytriphenylenes, whose mesomorphism was predicted earlier. The forecast is in good agreement with the experimental data. The effect of the introduction of the donor and acceptor groups into the central fragment of triphenylene on the phase transition temperature, texture, and range of existence of columnar mesophases is examined. The predicting ability of the molecular parameters suggested previously for the series under analysis is discussed. It is found that introduction of a nitro group, which is a strong electron acceptor, into the central fragment of triphenylene lowers the melting temperature of the compound versus its analog and does not promote columnar mesomorphism in the lower nonmesomorphous homologs. At the same time, this slightly expands the range of existence of the mesophase in higher homologs.

  DOI：

  10.1023/a:1010411804065
• 作为产物：
  描述：

  1,2-dinonylbenzene 在 三氯一氧化钒 三氯代氧化钒(V) 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到2,3,6,7,10,11-Hexakis(nonyloxy)triphenylene
  参考文献：
  名称：

  苯并芘和二苯并芘衍生物的合成：三氯氧化钒一种新型试剂

  摘要：

  本文介绍了一种使用 VOCl3 作为新型试剂制备各种三亚苯和二苯并芘衍生物的高效合成方法。用 VOCl3 氧化三聚法从邻二烷氧基苯得到了对称取代的六烷氧基三亚苯，产率很高。将 3,3′,4,4′-四烷氧基联苯与 1,2-二烷氧基苯或 1,2,3-三烷氧基苯氧化偶联，可得到不对称取代的三亚苯衍生物。该试剂可将 3,3′,4,4′-四烷氧基联苯高效氧化为 2,5,6,9,12,13-六烷氧基二苯并[fg,op]萘-1,8-醌及其 1,10-醌 异构体。这两种醌类化合物都可以利用成熟的化学方法转化为液晶衍生物。研究了溶剂、试剂浓度、酸催化剂和温度的影响。

  DOI：

  10.1055/s-2001-10821

文献信息

• Synthesis and specific features of mesomorphic behavior of new polysubstituted triphenylenes
  作者：O. V. Zemtsova、K. N. Zheleznov

  DOI：10.1007/s11172-005-0028-7

  日期：2004.8

  Previously unknown 2,3,6,7,10,11-hexakis(dodecyloxy)triphenylene and -(tetradecyloxy)triphenylene were synthesized. The structures of the synthesized compounds were proved by elemental analysis and spectral methods. Polymesomorphism was found for the first time and studied for substances of the hexaalkoxytriphenylene homologic series, as well as liotropic mesomorphism in a series of organic solvents

  合成了以前未知的 2,3,6,7,10,11-hexakis(dodecyloxy)triphenylene 和 -(tetradecyloxy)triphenylene。通过元素分析和光谱方法证实了合成化合物的结构。首次发现并研究了六烷氧基三亚苯基同系物质的多介晶现象，以及一系列有机溶剂中的异致介晶现象。
• Preparation of (η6-alkoxytriphenylene)tricarbonyl chromium(0) complexes
  作者：Jörg L Schulte、Sabine Laschat、Rasmus Schulte-Ladbeck、Volkmar von Arnim、Armin Schneider、Heino Finkelmann

  DOI：10.1016/s0022-328x(97)00586-x

  日期：1998.2

  (η6-hexaalkoxytriphenylene)Cr(CO)3 complexes 9 with varying alkyl chain lengths (C5H11 to C9H19) have been prepared with the chromium tricarbonyl moiety being exclusively attached to one terminal aryl ring. Differential scanning calorimetry, optical polarizing microscopy and X-ray diffraction showed that complexes 9a–d displayed isotropic melting behavior. However, hexanonyloxy-substituted complex 9e displayed a nematic

  新颖（η 6 -hexaalkoxytriphenylene）的Cr（CO）3个配合物9具有不同的烷基链长（C 5 H ^ 11至C 9 ħ 19）已准备与铬三羰基部分被排他地连接到一个终端芳基环。差示扫描量热法，光学偏振显微镜和X射线衍射表明，络合物9a-d显示出各向同性的熔融行为。然而，hexanonyloxy取代复杂9E显示向列Ñ d相37之间°和58℃。
• Nguyen Huu Tinh; Bernaud; Sigaud, Molecular Crystals and Liquid Crystals (1969-1991), 1981, vol. 65, # 3-4, p. 307 - 314
  作者：Nguyen Huu Tinh、Bernaud、Sigaud、Destrade

  DOI：——

  日期：——
• Triphenylene Columnar Liquid Crystals: Excited States and Energy Transfer
  作者：Dimitra Markovitsi、Arnaud Germain、Philippe Millie、Pierre Lecuyer、Lazaros Gallos、Panos Argyrakis、Holger Bengs、Helmut Ringsdorf

  DOI：10.1021/j100003a025

  日期：1995.1

  The present paper deals with the photophysical properties of columnar Liquid crystals formed by hexakis-(alkyloxy)triphenylenes. Absorption and fluorescence spectra of solutions are analyzed on the basis of quantum chemical calculations performed by the CS-INDO-CI (conformations spectra-intermediate neglect of differential overlap-configuration interaction) method: the absorption maximum is due to the S-0-->S-4 transition while fluorescence originates from the weak S-0-->S-1 transition. In columnar aggregates, the former transition corresponds to delocalized excited states while the latter corresponds to localized ones; calculation of intermolecular interactions shows that, at the temperature domain of the mesophases, all the molecules have the same excitation energy and, therefore, no spectral diffusion of the fluorescence is expected, in agreement with the time-resolved emission spectra. Excitation transfer is investigated by studying the fluorescence decays of mesophases doped with energy traps. Their analysis is made by means of Monte Carlo simulations considering both intracolumnar and intercolumnar jumps and using four different models for the distance dependence of the hopping probability. The best description is obtained with a model based on the extended dipole approximation and taking into account molecular orientation.
• Polysubstituted triphenylenes with active groups. Molecular parameters, synthesis, structure, and mesomorphism
  作者：O. B. Akopova、A. A. Bronnikova、A. Kruvchinskii、L. N. Kotovich、L. S. Shabyshev、L. A. Valkova

  DOI：10.1007/bf02873645

  日期：1998.11

  Molecular parameters of hexaalkoxybiphenylenes with different substituents on the periphery of the triphenylene nucleus of known and hypothetical structures are calculated, The probability of a discophase for compounds of this series is estimated from molecular parameters. Several compounds of this series having polar groups (NO2, NH2) in the I position of the triphenylene nucleus have been synthesized The compounds synthesized were investigated by thermopolarizing microscopy and X-ray diffraction analysis. The data on the mesomorphism of the new compounds are in good agreement with our prediction that alkoxytriphenylenes with polar groups have a discophase. It is established that introduction of an electron-accepting group at position I of the triphenylene nucleus expands the temperature range of existence of the discophase to room temperature. On the contrary, introduction of an electron-donating group narrows this interval. Compounds of this series presumably have a hexagonal columnar structure.