1-nitro-2,3,6,7,10,11-hexaheptyloxytriphenylene | 221147-18-8

• 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: 1-nitro-2,3,6,7,10,11-hexaheptyloxytriphenylene
• 英文别名: 2,3,6,7,10,11-Hexakis(heptyloxy)-1-nitrotriphenylene；2,3,6,7,10,11-hexaheptoxy-1-nitrotriphenylene
• CAS: 221147-18-8
• 化学式: C₆₀H₉₅NO₈
• 分子量: 958.416
• InChiKey: GXEYQSHDKCLVJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.8
• 重原子数：
  69
• 可旋转键数：
  42
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-nitro-2,3,6,7,10,11-hexaheptyloxytriphenylene 在 tin 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 1-amino-2,3,6,7,10,11-hexaheptyloxytriphenylene
  参考文献：
  名称：

  Synthesis and study of heptasubstituted triphenylenes with chiral fragments and predictable type of mesomorphism

  摘要：

  The forecasting of columnar and chiral mesomorphism was done for the new series of triphenylene derivatives. The mesomorphic properties of the two heptasubstituted triphenylenes containing chiral fragments were studied. The prediction results agreed well with the experimental data. Anilides of 1-amino-2,3,6,7,10,11-hexa(heptyloxy)triphenylene with abietic and dihydrocholic acids were found to exhibit the enantiotropic columnar dimesomorphism and to display the chiral columnar mesophases in the low-temperature range. The anilides obtained possess a lower thermal stability and extended interval of the mesophase existence than the initial amine.

  DOI：

  10.1134/s1070363210020155
• 作为产物：
  描述：

  hexaheptyloxytriphenylene 在 硝酸 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 生成 1-nitro-2,3,6,7,10,11-hexaheptyloxytriphenylene
  参考文献：
  名称：

  New Functionalised Derivatives of Hexaalkoxytriphenylene

  摘要：

  We report our latest. results on the development of functional triphenylene derivatives. Functionality can be introduced. directly into the nucleus by, for example, nitration. Analysis of our recently determined, single crystal x-ray structure of 1-nitro-2,3,6,7,10,11-hexaethoxytriphenylene (HAT2-NO2) suggests that the introduced dipole contributes significantly to the stability of the columnar structure. Synthesis of selectively hydroxylated alkoxytriphenylenes allows the functionalisation of one or more side-chains and we show examples of this in which the functional side-chain is: ethyleneoxy or ester or the side chain carries moieties such as: TTF, fullerene or crown-ether. The final section details new findings on crown-ether terminated hexaalkoxytriphenylene derivatives, which form lyotropic lamellar phases.

  DOI：

  10.1080/15421400490435288

文献信息

• ——
  作者：O. V. Zemtsova、O. K. Syromyatnikova、L. N. Kotovich、O. B. Akopova

  DOI：10.1023/a:1010411804065

  日期：——

  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.
• 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.
• Synthesis and investigation of triphenylene discotic derivatives with donor and acceptor groups and with predictable type of mesomorphism
  作者：O. B. Akopova、E. V. Kurbatova、M. S. Gruzdev

  DOI：10.1134/s1070363208100149

  日期：2008.10

  Prognosis of columnar mesomorphism is performed, five new hexa- and hepta-substituted triphenylene derivatives with donor and acceptor groups are synthesized and their mesomorphoc properties are stusied. Good agreement is achieved between predictions and experiments. The synthesized triphenylene derivatives are found to display enantiotropic columnar mesomorphism. 1-Amino-2,3,6,7,10,11-hexaheptyloxytriphenylene anilides of 2,3,5-triiodo-, 3,4,5-trihydroxy- and 4-nitro-benzoic acids reveal enantiotropic dimesomorphism. Also found decrease in thermal stability and extension of the interval of existence of mesophase at introduction to triphenylene frame of substituents with acceptor groups at the amino group.
• New Functionalised Derivatives of Hexaalkoxytriphenylene
  作者：Richard Bushby、Quanying Liu、Owen Lozman、Zhibao Lu、Sholto Mclaren

  DOI：10.1080/15421400490435288

  日期：2004.1

  We report our latest. results on the development of functional triphenylene derivatives. Functionality can be introduced. directly into the nucleus by, for example, nitration. Analysis of our recently determined, single crystal x-ray structure of 1-nitro-2,3,6,7,10,11-hexaethoxytriphenylene (HAT2-NO2) suggests that the introduced dipole contributes significantly to the stability of the columnar structure. Synthesis of selectively hydroxylated alkoxytriphenylenes allows the functionalisation of one or more side-chains and we show examples of this in which the functional side-chain is: ethyleneoxy or ester or the side chain carries moieties such as: TTF, fullerene or crown-ether. The final section details new findings on crown-ether terminated hexaalkoxytriphenylene derivatives, which form lyotropic lamellar phases.
• Effect of the nature of chiral fragment on mesomorphic properties of triphenylene ethers
  作者：O. B. Akopova、M. G. Bulavkova、M. S. Gruzdev、T. V. Frolova

  DOI：10.1134/s1070363211040165

  日期：2011.4

  A number of new 2,3,6,7,10,11-hexakis(heptyloxy)triphenylenes possessing a chiral substituent in position 1 of the triphenylene ring system and characterized by predictable mesomorphism were synthesized. The effect of the nature of the chiral fragment (dehydrocholic, lipoic, and d-tartaric acid residues) on the mesomorphic properties of triphenlylene ethers was studied. N-[2,3,6,7,10,11-hexakis(heptylozy)triphenylen-1-yl]amides derived from the above acids, unlike initial monomesomorphic amine, exhibit enantiotropic columnar polymorphism and give rise to helical columnar structure at reduced temperature. The newly synthesized amides are characterized by lower thermal stability and broader temperature range of the mesophase. Introduction of two chiral dehydrocholic acid fragments into the triphenylene core favors columnar (including chiral) mesomorphism.