3,6,10,11-四(正戊氧基)三亚苯基-2,7-二醇 | 102737-76-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 3,6,10,11-四(正戊氧基)三亚苯基-2,7-二醇
• 英文名称: 2,7-dihydroxy-3,6,10,11-tetrakis(pentyloxy)triphenylene
• 英文别名: 2,7-dihydroxy-3,6,10,11-tetra(pentyloxy)triphenylene；2,7-dihydroxy-3,6,10,11-tetra(pentoxy)triphenylene；3,6,10,11-Tetrakis(pentyloxy)triphenylene-2,7-diol；3,6,10,11-tetrapentoxytriphenylene-2,7-diol
• CAS: 102737-76-8
• 化学式: C₃₈H₅₂O₆
• 分子量: 604.827
• InChiKey: RRXLJTWVCLAAJD-UHFFFAOYSA-N

物化性质

• 熔点：
  105.0 °C
• 沸点：
  744.1±55.0 °C(Predicted)
• 密度：
  1.102

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  44
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-溴戊酸乙酯 、 3,6,10,11-四(正戊氧基)三亚苯基-2,7-二醇 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以74%的产率得到diethyl 5,5'-[3,6,10,11-tetrakis(pentyloxy)triphenylene-2,7-diylbis(oxy)]dipentanoate
  参考文献：
  名称：

  Synthesis and Characterization of Triphenylene Derivatives Containing Two Terminal Functional Groups at the Periphery

  摘要：

  Three novel series of triphenylene-based derivatives possessing functional group (ester, carboxylic acid, or hydroxy) at the ends of two aliphatic chains on the opposite position of triphenylene core have been synthesized and studied on mesomorphic properties. Their chemical structures were characterized by FT-IR, H-1-NMR, C-13-NMR, MS, and the thermotropic liquid crystalline properties were also investigated by polarizing optical microscopy, differential scanning calorimetry, and X-ray diffraction. It is found that the triphenylene derivatives containing terminal carboxylic acid or hydroxyl chains in the series of 9 or 10 show themortropic columnar mesophase, while the corresponding derivatives possessing terminal esters don't show any mesomorphism.

  DOI：

  10.1080/15421400801915084
• 作为产物：
  描述：

  1,2-bis(pentyloxy)benzene 在 iron(III) chloride 、 正丁基锂 、 硫酸 、 二苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 3,6,10,11-四(正戊氧基)三亚苯基-2,7-二醇
  参考文献：
  名称：

  Highly ordered columnar superlattice nanostructures with improved charge carrier mobility by thermotropic self-assembly of triphenylene-based discotics

  摘要：

  一系列在不同取代位置具有两个酯基团的三苯基酯被合成并研究。3,6-取代分子形成了螺旋六角柱状超结构，从而提高了载流子迁移率。

  DOI：

  10.1039/c9tc04349g

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。
• 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.
• Closs, Fritz; Haeubling, Lukas; Henderson, Philippe, Journal of the Chemical Society. Perkin transactions I, 1995, # 7, p. 829 - 838
  作者：Closs, Fritz、Haeubling, Lukas、Henderson, Philippe、Ringsdorf, Helmut、Schuhmacher, Peter

  DOI：——

  日期：——
• Synthesis of Functionalized Triphenylenes by Selective Ether Cleavage with B-Bromocatecholborane
  作者：Sandeep Kumar、M. Manickam

  DOI：10.1055/s-1998-2133

  日期：1998.8

  This paper presents an efficient synthetic procedure for the preparation of mono-, di- and trifunctionalized triphenylene derivatives starting from the readily available hexakis(pentyl oxy)triphenylene by selective ether cleavages with B-bromocate-cholborane (2-bromo-1,3,2-benzodioxaboroles). Functionalized triphenylene derivatives are the precursor molecules for the preparation of processible triphenylene discotic dimers, oligomers, polymers and networks.