2,6,10-trihydroxy-3,7,11-tris(pentyloxy)triphenylene | 168847-20-9

• 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: 2,6,10-trihydroxy-3,7,11-tris(pentyloxy)triphenylene
• 英文别名: 2,6,10-tris(pentyloxy)-3,7,11-trihydroxytriphenylene；2,6,10-trihydroxy-3,7,11-tri(pentyloxy)triphenylene；2,6,10-trihydroxy-3,7,11-tripentyloxy-triphenylene；2,6,10-trihydroxy-3,7,11-tri(pentoxy)triphenylene；2,6,10-trihydroxy-3,7,11-tripentyloxytriphenylene；2,6,10-Triphenylenetriol, 3,7,11-tris(pentyloxy)-；3,7,11-tripentoxytriphenylene-2,6,10-triol
• CAS: 168847-20-9
• 化学式: C₃₃H₄₂O₆
• 分子量: 534.693
• InChiKey: OMZDPJXSDJLHQU-UHFFFAOYSA-N

物化性质

• 沸点：
  725.7±55.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6,10-trihydroxy-3,7,11-tris(pentyloxy)triphenylene 在 palladium on activated charcoal 5-氯-1-苯基-1H-四唑 、 氢气 、 溴 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成
  参考文献：
  名称：

  Synthesis of novel mixed tail triphenylene discotic liquid crystals—the search for higher order

  摘要：

  Tribromo-trialkoxytriphenylenes and trialkoxytriphenylenes are derivatized directly on a polyaromatic core to give novel discotic liquid crystals radially substituted symmetrically and asymmetrically with two different functionalities.

  DOI：

  10.1039/cc9960001031
• 作为产物：
  描述：

  2,6,10-trimethoxy-3,7,11-tripentyloxytriphenylene 在 碘代三甲硅烷 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以36%的产率得到2,6,10-trihydroxy-3,7,11-tris(pentyloxy)triphenylene
  参考文献：
  名称：

  Coordinative Nanoporous Polymers Synthesized with Hydrogen-Bonded Columnar Liquid Crystals

  摘要：

  本文报道了一种纳米多孔聚合物的开发，该聚合物表现出对锌卟啉的配位性质。一种由三苯并环模板和三个等量的周围树枝状两性分子组成的氢键柱状液晶前驱体，后者具有吡啶基头基和可聚合的脂肪链，通过光聚合反应共价固定，随后选择性去除模板，依次形成了一种纳米多孔聚合物，其孔壁修饰有吡啶基团。这种纳米多孔聚合物反映了模板的构象，并显示出吡啶基团对锌卟啉的显著配位能力。这种配位的纳米多孔聚合物有望作为将染料组织成功能性超分子结构的纳米级支架。

  DOI：

  10.1166/jnn.2012.6600

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 Mesomorphism of Novel Chiral Triphenylene-Based Discotic Liquid Crystals
  作者：Yu-Ting Liao、Ke-Qing Zhao、Li Wang、Ping Hu、Bi-Qin Wang

  DOI：10.1080/15421406.2011.569691

  日期：2011.6.30

  A series of new chiral triphenylene-based discotic liquid crystals with one or three chiral soft chains were synthesized through Mitsunobu reactions. Yields of the chiral discotic liquid crystals were achieved up to 84%. Chemical structures were confirmed by 1H NMR; and mesomorphism was studied by polarized optical microscopy as well as by differential scanning calorimetry. The mesomorphic studies

  通过光信反应合成了一系列具有一个或三个手性软链的新型手性苯并苯基盘状液晶。手性盘状液晶的产率高达 84%。化学结构经1H NMR确证；通过偏光显微镜和差示扫描量热法研究了介晶现象。介晶研究表明：1）手性盘状体具有六角柱状或塑性柱状中间相；2）将手性引入三亚苯基盘状液晶可以通过降低熔点来扩大中间相范围。此外，还观察到了介晶现象的意外奇偶效应。
• A Hydrogen-bonded Supramolecular Hexagonal Columnar Liquid Crystal Composed of a Tricarboxylic Triphenylene and Monopyridyl Dendrons
  作者：Shinsuke Ishihara、Yuusuke Furuki、Shinji Takeoka

  DOI：10.1246/cl.2007.282

  日期：2007.2

  Tricarboxylic triphenylene (TPC5) and monopyridyl dendron (DenC12) were mixed in 1:2, 1:3, and 1:4 molar ratios, and investigation by IR, DSC, and XRD studies proved that TPC5 and DenC12 self-assembled to form a hexagonal columnar liquid crystal with 1:3 molar stoichiometry via complementary hydrogen-bonds.

  三羧酸三苯并芘（TPC5）和单吡啶树枝状聚合物（DenC12）按1:2、1:3和1:4的摩尔比混合，通过红外光谱（IR）、差示扫描量热法（DSC）和X射线衍射（XRD）研究表明，TPC5和DenC12通过互补氢键自组装形成了具有1:3摩尔化学计量比的六方柱状液晶。
• Synthesis of functionalized triphenylene discotic liquid crystals and the influence of unsaturated periphery on mesomorphism
  作者：KeQing Zhao、Hui Zhou、WenHao Yu、Ping Hu、BiQin Wang、Hirosato Monobe、Yo Shimizu

  DOI：10.1007/s11426-011-4325-8

  日期：2011.10

  Twelve triphenylene discogens with unsaturated periphery (abbreviated as C18H6(OC5H11)6−x (OR) x (x = 1, 2, 3), R = -C3H6CH == CH2 (a), -C3H6C C ≡CH (b), -C2H4OCH== CH2 (c)) were synthesized and characterized. The thermotropic liquid crystal properties were studied by using polarized optical microscopy, differential scanning calorimetry and X-ray diffractometry. The results showed that all triphenylenes exhibited hexagonal columnar mesophase. The thermotropic studies showed that series a (alkene periphery) exhibited higher clearing points than the corresponding series b (alkyne periphery), while series c (vinyloxy periphery) exhibited highest clearing points and widest mesophase temperature ranges. We also found that the symmetric discogens sym-C18H6(OC5H11)3(OR)3 displayed higher melting points and clearing points than the asymmetric ones asym-C18H6(OC5H11)3(OR)3.

  具有不饱和外围的十二个苯并菲二元（缩写为 C18H6(OC5H11)6−x (OR) x (x = 1, 2, 3)，R = -C3H6CH == CH2 (a)，-C3H6C C ≡CH (b)，合成并表征了-C2H4OCH==CH2(c))。利用偏光显微镜、差示扫描量热法和X射线衍射法研究了热致液晶特性。结果表明，所有苯并菲均呈现六方柱状中间相。热致研究表明，a系列（烯烃外围）比相应的b系列（炔外围）表现出更高的清亮点，而c系列（乙烯基氧基外围）表现出最高的清亮点和最宽的中间相温度范围。我们还发现对称的disogens sym-C18H6(OC5H11)3(OR)3 比不对称的disogens asym-C18H6(OC5H11)3(OR)3 显示出更高的熔点和澄清点。
• A Modified Procedure for the Synthesis of C3-Symmetric 'Mixed-Tail' Triphenylenes
  作者：Paul T. Wright

  DOI：10.1055/s-1997-1309

  日期：1997.9

  A modified procedure of the selective cleavage of three of the pentyloxy groups from 2,3,6,7,10,11-hexapentyloxytriphenylene (1) to give C3-symmetric 2,6,10-trihydroxy-3,7,11-tripentyloxytriphenylene (2) is described. The methodology has been extended to provide a convenient route to the C3-symmetric triphenylene derivative 8, with orthogonally protected carboxylic acid groups.

  本文描述了一种改良的从2,3,6,7,10,11-六戊氧基三苯基（1）中选择性裂解三个戊氧基团得到C3-对称2,6,10-三羟基-3,7,11-三戊氧基三苯基（2）的方法。该方法已被扩展为一种制备C3-对称三苯基衍生物8的便捷途径，其中羧酸基团具有正交保护。