2,3,6,7-tetrakis-hexyloxy-phenanthrene-9,10-dione | 153399-74-7

• 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: 2,3,6,7-tetrakis-hexyloxy-phenanthrene-9,10-dione
• 英文别名: 2,3,6,7-tetrais(hexyloxy)-phenanthrene-9,10-dione；2,3,6,7-Tetrahexoxyphenanthrene-9,10-dione
• CAS: 153399-74-7
• 化学式: C₃₈H₅₆O₆
• 分子量: 608.859
• InChiKey: ZEJDVXKTFRRJSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  44
• 可旋转键数：
  24
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二氨基马来腈 、 2,3,6,7-tetrakis-hexyloxy-phenanthrene-9,10-dione 在 溶剂黄146 作用下， 反应 48.0h， 以57%的产率得到6,7,10,11-tetrakis-hexyloxy-dibenzo[f,h]quinoxaline-2,3-dicarbonitrile
  参考文献：
  名称：

  Synthesis of unsymmetrical dibenzoquinoxaline discotic mesogensElectronic supplementary information (ESI) available: full synthetic and analytical details, POM images. See http://www.rsc.org/suppdata/cc/b4/b400998c/

  摘要：

  不对称二苯并吡咯烯盘状介质是通过相应的四烷氧基苯基甲酰衍生物制备的。这些二苯并吡咯烯在极其广泛的温度范围内展现出Colho相。

  DOI：

  10.1039/b400998c
• 作为产物：
  描述：

  1,2-bis(3,4-bis(hexyloxy)phenyl)ethane-1,2-dione 在 三氟代氧化钒(V) 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以96%的产率得到2,3,6,7-tetrakis-hexyloxy-phenanthrene-9,10-dione
  参考文献：
  名称：

  Synthesis of unsymmetrical dibenzoquinoxaline discotic mesogensElectronic supplementary information (ESI) available: full synthetic and analytical details, POM images. See http://www.rsc.org/suppdata/cc/b4/b400998c/

  摘要：

  不对称二苯并吡咯烯盘状介质是通过相应的四烷氧基苯基甲酰衍生物制备的。这些二苯并吡咯烯在极其广泛的温度范围内展现出Colho相。

  DOI：

  10.1039/b400998c

文献信息

• Enforced liquid crystalline properties of dibenzo[a,c]phenazine dimer and self assembly
  作者：Mei-Chun Tzeng、Su-Chih Liao、Tsu-Hsin Chang、Shih-Chi Yang、Min-Wei Weng、Hsiao-Ching Yang、Michael Y. Chiang、Zhang Kai、Jishan Wu、Chi Wi Ong

  DOI：10.1039/c0jm01636e

  日期：——

  Dibenzo[a,c]phenazine dimers with the following features: (i) short spacer, (ii) peripheral chains shorter and longer than the spacers, and (iii) reduced symmetrical structure of the disc were synthesized. The dibenzo[a,c]phenazine disc has enforced the self-assembly of discotic dimers connected through six methylene spacers to form mesophases through a folded conformation in the mesophase. An X-ray diffraction study pinpoints the preferential intra-molecular bridging conformation of these dimers at the mesophase. These new discotic dimers showed polymesomorphism and glass formation. Interestingly, these discotic dimers form organogels with non-polar hydrocarbon solvents and long chain aliphatic alcohols. A superstructure arising from association of the nanofibers was observed with transmission electron microscopy.

  具有以下特征的二苯并[a,c]菲嗪二聚体被合成出来：(i) 短间隔基，(ii) 周边链比间隔基短和长，(iii) 碟片对称结构减少。二苯并[a,c]菲嗪碟片通过六个亚甲基间隔基连接，强化了碟状二聚体的自组装，形成通过折叠构象形成的介相。X射线衍射研究确定了这些二聚体在介相中的优先分子内桥接构象。这些新的碟状二聚体显示出高分子多形性和玻璃化形成特性。有趣的是，这些碟状二聚体能够与非极性烃类溶剂和长链脂肪醇形成有机凝胶。透射电子显微镜观察到了由纳米纤维聚集形成的超结构。
• Self-assembly of hydrogen-bonded molecules: discotic and elliptical mesogens
  作者：E. Johan Foster、Christine Lavigueur、Ying-Chieh Ke、Vance E. Williams

  DOI：10.1039/b503310a

  日期：——

  The effect of hydrogen bonding on the phase behaviour of discotic mesogens was investigated with a series of dibenzophenazine carboxylic acids and their methyl ester analogues. The esters exhibit only columnar hexagonal phases, while the acids form columnar hexagonal, columnar rectangular and nematic mesophases. The acids have much higher transition temperatures and supercool to room temperature while maintaining the liquid crystalline ordering. These differences could be explained by the ability of the acids to form hydrogen-bonded dimers, which may also be regarded as supramolecular elliptically-shaped mesogens.

  研究了氢键对盘状介质相行为的影响，使用了一系列二苯并呋喃酸及其甲基酯类似物。酯类仅表现出柱状六角相，而酸类则形成柱状六角相、柱状矩形相和向列相。酸类的相变温度显著更高，并能够在保持液晶有序的情况下超冷至室温。这些差异可以通过酸类形成氢键二聚体的能力来解释，这些二聚体也可以被视为超分子椭圆形介质。
• From S,N‐Heteroacene to Large Discotic Polycyclic Aromatic Hydrocarbons (PAHs): Liquid Crystal versus Plastic Crystalline Materials with Tunable Mechanochromic Fluorescence
  作者：Wei Yuan、Xiang‐Kui Ren、Mengwei Li、Hongshuang Guo、Yi Han、Mengjiao Wu、Qi Wang、Miaomiao Li、Yulan Chen

  DOI：10.1002/anie.201801488

  日期：2018.5.22

  from S,N heteroatoms facilitates the formation of highly ordered columnar superstructures both in solution and bulk. Columnar mesophases, including liquid crystal (LC) and plastic crystal (PC) assemblies could form unprecedentedly based on the same PAH core. The cores are delicately modulated by the peripherical alkoxy chains. Both mesogens have mechanochromic fluorescent (MCF) character, which is also

  基于扩大的二苯并[ a，c ]吩嗪核的新型盘状多环芳烃（PAH）已经开发出来。源自S，N杂原子的偶极矩增加的大共轭介晶核，有助于在溶液和本体中形成高度有序的柱状上部结构。基于相同的PAH核，包括液晶（LC）和塑料晶体（PC）组件在内的柱状中间相可能会空前地形成。核心被外围的烷氧基链精细地调节。两种介晶均具有机械变色荧光（MCF）特征，该特征也取决于结构并与不同的中间相形成相关。首次在如此大的共轭介晶体系中实现了MCF特性。
• Strategies for promoting discotic nematic phases
  作者：Carson O. Zellman、Vance E. Williams

  DOI：10.1039/d3sm00212h

  日期：——

  A series of discotic dimers were synthesized in an attempt to obtain nematic discotic liquid crystal phases. Although initial target compounds were nonmesogenic, the incorporation of bulky groups adjacent to the ester bridge, in conjunction with peripheral chains of mixed length, were used to promote the formation of an enantiotropic nematic phase.

  合成了一系列盘状二聚体以试图获得向列盘状液晶相。尽管最初的目标化合物是非介晶的，但在酯桥附近加入庞大的基团，结合混合长度的外围链，被用来促进对映体向列相的形成。
• Structural Factors Controlling the Self-Assembly of Columnar Liquid Crystals
  作者：E. Johan Foster、R. Bradley Jones、Christine Lavigueur、Vance E. Williams

  DOI：10.1021/ja0613198

  日期：2006.7.1

  A series of disc-shaped molecules were prepared by the condensation of 1,2-diamines with 2,3,6,7-tetrakis(hexyloxy) phenanthrene-9,10-dione to investigate the relationship between changes in molecular structure and the self-assembly of columnar liquid crystalline phases. A comparison of compounds with different core sizes indicated that molecules with larger aromatic cores had a greater propensity to form columnar phases, as did compounds substituted with electron-withdrawing groups. In contrast, molecules with electron-donating substituents were nonmesogenic. The clearing temperature of columnar phases increased linearly with the electron-withdrawing ability of the substituents, as quantified by Hammett sigma-values. The observed trends can be rationalized in terms of the strength of pi-pi interactions between aromatic cores in the liquid crystalline phases and suggest that both electrostatic interactions and dispersion forces play important roles in the self-assembly of these materials.