hexaheptyloxytriphenylene | 69079-53-4

• 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: hexaheptyloxytriphenylene
• 英文别名: 2,3,6,7,10,11-hexa(heptyloxy)triphenylene；2,3,6,7,10,11-hexaheptyloxytriphenylene；hexakis(heptyloxy)triphenylene；2,3,6,7,10,11-Hexakis(heptyloxy)triphenylene；2,3,6,7,10,11-hexaheptoxytriphenylene
• CAS: 69079-53-4
• 化学式: C₆₀H₉₆O₆
• 分子量: 913.419
• InChiKey: GDYRXNRKOCDNBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  890.6±60.0 °C(Predicted)
• 密度：
  1.07 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  22
• 重原子数：
  66
• 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：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  hexaheptyloxytriphenylene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以42%的产率得到2-hydroxy-3,6,7,10,11-pentaheptyloxy-triphenylene
  参考文献：
  名称：

  A Convenient Route to 2-(Hydroxy)-3,6,7,10,11-pentaalkyloxytriphenylenes

  摘要：

  Unsymmetrical monohydroxypentaalkoxytriphenylenes have been conveniently prepared from the readily accessible symmetrical hexaalkyloxytriphenylenes using boron tribromide mediated ether cleavage.

  DOI：

  10.1080/00397919708007297
• 作为产物：
  描述：

  1-碘庚烷 在 potassium fluoride 、 硫酸 、 potassium hydroxide 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 hexaheptyloxytriphenylene
  参考文献：
  名称：

  Effect of the nature of chiral fragment on mesomorphic properties of triphenylene ethers

  摘要：

  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.

  DOI：

  10.1134/s1070363211040165

文献信息

• Intermolecular organisation of triphenylene­based discotic mesogens by interdigitation of alkyl chains
  作者：Matthew T. Allen、Siegmar Diele、Kenneth D.M. Harris、Torsten Hegmann、Benson M. Kariuki、Dirk Lose、Jon A. Preece、Carsten Tschierske

  DOI：10.1039/b006916g

  日期：——

  Two series of hexakis(alkyloxy)triphenylenes have been synthesised and characterised. All materials contain two different lengths of n-alkyloxy chains. Series I (C5Cn) materials contain three –OC5H11 chains and three –OCnH2n + 1 chains. Series II (CmCn) materials contain three –OCmH2m + 1 chains and three –OCnH2n + 1 chains, such that m + n  = 10. Hexagonal columnar mesophases are observed in Series I for n ≥ 3 and, in Series II, for C5C5 and C6C4. Investigation by XRD shows that, within Series I, increasing the Cn chain length increases the intercolumnar spacing. Furthermore, the intercolumnar spacings for constitutional isomers are identical. The difference in the lengths of the two types of alkyl chain at the periphery of the molecules is defined as the Interdigitation Length (IL) and is a measure of the maximum extent of interdigitation that is possible between neighbouring molecules. Series I and II materials have been studied to probe the effect of IL on the change in enthalpy (ΔHCol–I) and entropy (ΔSCol–I) for the mesophase to isotropic liquid phase transition. In contrast to CxCx materials, which show a decrease in ΔHCol–I and ΔSCol–I with increasing chain length, Series I and II mesogens all exhibit ΔHCol–I and ΔSCol–I values similar to those of long chain CxCx materials, irrespective of chain length.

  已合成并表征两系列六烷基醚三苯基烯。所有材料均包含两种不同长度的n-烷氧基链。系列I (C5Cn) 材料包含三条 –OC5H11 链和三条 –OCnH2n + 1 链。系列II (CmCn) 材料包含三条 –OCmH2m + 1 链和三条 –OCnH2n + 1 链，其中 m + n = 10。系列I在 n ≥ 3 时观察到六方柱状介相，而系列II则在 C5C5 和 C6C4 时观察到。XRD研究显示，在系列I中，增加Cn链的长度会增加柱间距。此外，构象异构体的柱间距是相同的。分子外周两种烷基链长度的差异被定义为交错长度（IL），它是衡量相邻分子之间最大交错程度的指标。研究了系列I和II材料，以探讨IL对介相到各向同性液相转变的焓变化（ΔHCol–I）和熵变化（ΔSCol–I）的影响。与CxCx材料不同，CxCx材料在链长增加时ΔHCol–I和ΔSCol–I均减少，而系列I和II的介晶体在ΔHCol–I和ΔSCol–I值上都与长链CxCx材料相似，而与链长无关。
• 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。
• Highly oriented fibres of discotic liquid crystals
  作者：Long Y. Chiang、C. R. Safinya、N. A. Clark、K. S. Liang、A. N. Bloch

  DOI：10.1039/c39850000695

  日期：——

  Highly aligned discotic liquid crystal fibres of hexa-alkoxytriphenylene (HET-n) and its ester derivative (HAT-n) can be drawn by a new strand technique; our synchrotron X-ray scattering study indicates the single crystal quality of these fibres.

  六烷氧基三亚苯基（HET- n）及其酯衍生物（HAT- n）的高度取向的盘状液晶纤维可以通过新的绞合技术进行拉伸。我们的同步加速器X射线散射研究表明这些纤维的单晶质量。
• Synthesis and characterisation of novel hexaalkoxytriphenylenes bearing an additional alkyl chain in the α-position
  作者：Andrew N. Cammidge、Hemant Gopee、Hitesh Patel

  DOI：10.1016/j.tetlet.2009.03.089

  日期：2009.7

  Exhaustive alkylation of hexahydroxytriphenylene results in production of significant quantities of a side product bearing one additional alkyl chain originating from C-alkylation. A series of these novel materials have been isolated and characterised to gain further insight on factors controlling mesophase formation in triphenylene discotics.

  六羟基三亚苯基的穷举烷基化导致大量副产物的产生，所述副产物带有一个源自C-烷基化的另外的烷基链。已分离并表征了一系列这些新颖的材料，以进一步了解控制三亚苯基圆盘形中间相形成的因素。
• 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℃。