2,7,10-trihydroxy-3,6,11-tris(pentyloxy)triphenylene | 168847-28-7

• 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: 2,7,10-trihydroxy-3,6,11-tris(pentyloxy)triphenylene
• 英文别名: 2,7,10-tris(pentyloxy)-3,6,11-trihydroxytriphenylene；2,7,10-trihydroxy-3,6,11-tripentyloxy-triphenylene；2,6,11-trihydroxy-3,7,10-tri(pentoxy)triphenylene；2,6,11-Triphenylenetriol, 3,7,10-tris(pentyloxy)-；3,7,10-tripentoxytriphenylene-2,6,11-triol
• CAS: 168847-28-7
• 化学式: C₃₃H₄₂O₆
• 分子量: 534.693
• InChiKey: QEHRUZPTJZXJKN-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：

  2,7,10-trihydroxy-3,6,11-tris(pentyloxy)triphenylene 在 palladium on activated charcoal 5-氯-1-苯基-1H-四唑 、 氢气 、 sodium hydride 作用下， 生成 2,6,11-Tris-pentyloxy-triphenylene
  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：

  2,3,6,7,10,11-六(戊氧基)三亚苯基 在 9-BrBBN 作用下， 以 二氯甲烷 为溶剂， 反应 38.0h， 以42%的产率得到2,6,10-trihydroxy-3,7,11-tris(pentyloxy)triphenylene
  参考文献：
  名称：

  Intermolecular organisation of triphenylene­based discotic mesogens by interdigitation of alkyl chains

  摘要：

  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。

  DOI：

  10.1039/b006916g

文献信息

• 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。
• Triphenylene/Carbazole Mesogens and Their Electrochemistry
  作者：M. Manickam、Graeme Cooke、Sandeep Kumar、Peter R. Ashton、Jon A. Preece、Neil Spencer

  DOI：10.1080/714965597

  日期：2003.1
• Tuning Hydrogen-Bonding with Amide Groups for Stable Columnar Mesophases of Triphenylene Discogens
  作者：B. Q. Wang、K. Q. Zhao、P. Hu、W. H. Yu、C. Y. Gao、Y. Shimizu

  DOI：10.1080/15421400701680937

  日期：2007.12.4
• ——
  作者：M. Manickam、Maura Belloni、Sandeep Kumar、Sanjay K. Varshney、D. S. Shankar Rao、Peter R. Ashton、Jon A. Preece、Neil Spencer

  DOI：10.1039/b103052n

  日期：2001.10.23

  The synthesis of 13 discotic mesogens is described in which the well-known hexakis( pentyloxy) triphenylene liquid crystalline material has been chemically modified to incorporate one, two, three and six carbazole moieties. These modifications have been achieved by the alkylation or esterification of mono-, di-, tri- and hexa-hydroxytriphenylene derivatives with alkyl bromides and carboxylic acids incorporating the carbazole moiety. The pure compounds are not liquid crystalline in nature but when doped with TNF, hexagonal columnar mesophases are induced, as shown by DSC, OPM and X-ray diffraction. These mesophases exist below room temperature. The mesophase clearing temperatures are dependent on several factors including the chain length separating the carbazole moiety from the triphenylene core, and the nature of the ether or ester linkage, and the degree of TNF doping. The data suggest that the most stable mesophases (highest clearing temperatures) are formed when a 2 : 1 complex is formed between the carbazole derivatives and the TNF, respectively. The correlation length obtained from X-ray diffraction reveals that the columnar order for one of the ether derivatives decreases, whereas the correlation length increases for one of the ester derivatives. This result suggests that the TNF is not only partaking in pi-pi noncovalent bonding interactions, but also in polar interactions with the C=O bond. Such mesogenic carbazole derivatives may have advantageous photorefractive properties over the amorphous polymeric materials.