2,3,6,7-tetrakis-octyloxy-phenanthrene-9,10-dione | 791637-70-2

• 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-octyloxy-phenanthrene-9,10-dione
• 英文别名: 2,3,6,7-tetraoctyloxyphenanthrene-9,10-dione；2,3,6,7-Tetraoctoxyphenanthrene-9,10-dione
• CAS: 791637-70-2
• 化学式: C₄₆H₇₂O₆
• 分子量: 721.074
• InChiKey: DHHRFMGUYSHEEU-UHFFFAOYSA-N

物化性质

• 沸点：
  785.7±60.0 °C(predicted)
• 密度：
  1.005±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.2
• 重原子数：
  52
• 可旋转键数：
  32
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  2,3,6,7-tetrakis-octyloxy-phenanthrene-9,10-dione 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 1,1'-((2,3,6,7-tetrakis(octyloxy)dibenzo[a,c]phenazine-11,12-diyl)bis(azanediyl))bis(dodec-1-en-3-one)
  参考文献：
  名称：

  Mesogenic Enaminoketone Ni(II) Complexes of Phenazine and Quinoxaline Derivatives

  摘要：

  The new Ni(II) metallomesogenes were synthesized. Their mesogenic cores are constructed from tetradental enaminoketone unit connected to 1,2: 3,4-di(4,5-dioctyloxybenzo) phenazine or 2,3-di(3,4-dioctyloxyphenylo) quinoxaline. The described compounds form columnar hexagonal phase (Col(hd)) in very broad temperature range. The high stability of the columnar phase results from presence of a permanent dipol moment in enaminoketone moieties created by strong electron withdrawing properties of carbonyl groups.

  DOI：

  10.1080/15421406.2011.653714
• 作为产物：
  描述：

  1,2-bis(3,4-bis(octyloxy)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94%的产率得到2,3,6,7-tetrakis-octyloxy-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。
• Dibenzo[a,c]phenazine with six-long alkoxy chains to probe optimization of mesogenic behavior
  作者：Chi Wi Ong、Ja-Yi Hwang、Mei-Chun Tzeng、Su-Chih Liao、Hsiu-Fu Hsu、Tsu-Hsin Chang

  DOI：10.1039/b617827h

  日期：——

  New hexaalkoxydibenzo[a,c]phenazines (HDBPs) with six-carbon long chains have been prepared, and their mesogenic behavior investigated. The incorporation of six peripheral alkoxy groups onto the larger, dipolar core bearing nitrogen atoms showed interesting thermal properties. The crystal-to-mesophase transitions for the HDBPs (K–col) are similar to the triphenylenes, but the clearing temperatures (Col–I) are shifted upwards by approx. 60 °C. HDBP therefore possesses stable hexagonal mesophases in a fairly broad temperature range and form homeotropically aligned films.

  新合成的具有六碳长链的新型六烷氧基二苯并[a,c]吩嗪类化合物（HDBP），其液晶行为已被研究。通过将六个外围烷氧基团引入到具有氮原子的大偶极核心结构中，展现出有趣的温度特性。HDBP的晶体至液晶相转变（K–col）与三苯化合物相似，但其清亮点（Col–I）温度提高了约60°C。因此，HDBP具有在相当宽的温度范围内稳定的六方液晶相，并能形成垂直排列的薄膜。
• 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。
• Indent and bulge-discogens for controlling the columnar mesophase
  作者：Chi Wi Ong、Chia-Yi Hwang、Su-Chih Liao、Cheng-Hao Pan、Tsu-Hsin Chang

  DOI：10.1039/b904981a

  日期：——

  Two series of dibenzophenazines with their mesogenic cores substituted by indent or bulge peripheral side chains have been synthesized. A good balance between anisotropy and isotropy has been achieved by the tri-functionalized bulge-discogen having a pair of interdigitating alkoxy chains. On cooling, the tri-functionalized bulge-discogen with a low melting temperature and high clearing temperature remains liquid crystalline at room temperature.

  两系列双苯并呋喃的化合物已合成，其介晶核心被凹进或鼓起的外围侧链取代。通过具有一对交错的烷氧基链的三官能化鼓起盘状分子，达到了各向异性和各向同性之间的良好平衡。在降温过程中，具有低熔点和高清除温度的三官能化鼓起盘状分子在室温下仍保持液晶态。
• 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/
  作者：E. Johan Foster、Jarret Babuin、Natalie Nguyen、Vance E. Williams

  DOI：10.1039/b400998c

  日期：——

  Unsymmetrical dibenzophenazine discotic mesogens were prepared via the corresponding tetraalkoxybenzil derivatives. These dibenzophenazines exhibit Colho phases over extremely broad temperature ranges.

  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。