1,2-bis(3,4-bis(hexyloxy)phenyl)ethane-1,2-dione | 138145-24-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-bis(3,4-bis(hexyloxy)phenyl)ethane-1,2-dione
• 英文别名: 1,2-bis-(3,4-dihexoxyphenyl)ethanedione；3,3',4,4'-Tetrakis(hexyloxy)benzil；3,3',4,4'-tetrakis-hexyloxybenzil；3,3,4,4'-tetra-n-hexyloxybenzyl；Ethanedione, bis[3,4-bis(hexyloxy)phenyl]-；1,2-bis(3,4-dihexoxyphenyl)ethane-1,2-dione
• CAS: 138145-24-1
• 化学式: C₃₈H₅₈O₆
• 分子量: 610.875
• InChiKey: CFEGAZCQTCNMFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  44
• 可旋转键数：
  27
• 环数：
  2.0
• 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：

  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
• 作为产物：
  描述：

  邻苯二酚 在 三氯化铝 、 potassium carbonate 作用下， 以 二硫化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 1,2-bis(3,4-bis(hexyloxy)phenyl)ethane-1,2-dione
  参考文献：
  名称：

  Synthesis of alkyl- and alkoxy-substituted benzils and oxidative coupling to tetraalkoxyphenanthrene-9,10-diones

  摘要：

  Intermolecular Friedel-Crafts acylation of various substituted alkyl- or alkoxybenzenes with oxalyl chloride using carbon disulfide as solvent gave rise to the benzils 1a-k. Subsequent intramolecular oxidative coupling with either thallium(III) oxide/trifluoroacetic acid or vanadium(V) oxyfluoride/boron trifluoride diethyl etherate resulted in the corresponding phenanthrene-9,10-diones 2a-d. It has been shown that oxygen functionalities at the 3, 3', 4, and 4' positions are necessary for coupling to occur. These substituted benzils and phenanthrene-9,10-diones constitute precursors for ligands in the field of discotic metallomesogens or polymeric mesogens.

  DOI：

  10.1021/jo00082a022

文献信息

• Pyrazine-incorporating panchromatic sensitizers for dye sensitized solar cells under one sun and dim light
  作者：Mulu Berhe Desta、Nguyễn Sơn Vinh、CH. Pavan Kumar、Sumit Chaurasia、Wei-Ti Wu、Jiann T. Lin、Tzu-Chien Wei、Eric Wei-Guang Diau

  DOI：10.1039/c8ta04774j

  日期：——

  π-conjugated bridge, and A = electron acceptor/anchor) sensitizers with two bis(alkoxy)phenyl substituents incorporating thieno[3,4-b]pyrazines (TP) or a benzo[3,4-b]pyrazine (BP) entity as the auxiliary acceptor have been synthesized for application in dye-sensitized solar cells (DSSCs). Under 1 sun illumination, the DSSCs fabricated from the two BP dyes with a co-adsorbent have efficiencies of 8.39% and

  新型D–A'–π–A型（D =电子供体，A'=辅助受体，π=π共轭桥，A =电子受体/锚）敏化剂，带有两个结合噻吩并[3]的双（烷氧基）苯基取代基，4- b ]吡嗪（TP）或苯并[3,4 b ]吡嗪（BP）实体作为辅助受体已被合成为在染料敏化太阳能电池（DSSC）应用程序。在1个阳光照射下，由两种BP染料与助吸附剂制成的DSSC的效率分别为8.39％和9.03％。后者超过了标准的N719染料（8.87％）。在昏暗的光线条件下MD7 在300 lux和6000 lux的辐照度下，功率转换效率分别为18.95％和27.17％。
• 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。
• Discotic Liquid Crystals of Transition Metal Complexes. XVI. Discotic Mesomorphism and Unique Chromism of Bis[1,2-bis(3,4-dialkoxyphenyl)ethanedione dioximato]palladium(II) Complexes
  作者：Kazuchika Ohta、Mitsuo Moriya、Mayumi Ikejima、Hiroshi Hasebe、Tetsuya Fujimoto、Iwao Yamamoto

  DOI：10.1246/bcsj.66.3553

  日期：1993.12

  Bis[1,2-bis(3,4-dialkoxyphenyl)ethanedione dioximato]palladium(II) complexes, (abbreviated [Pd(CnO)4dpg}2]; n = 1—12)have been synthesized and characterized. It was found that each of the [Pd(CnO)4dpg}2] (n = 2—12) complexes has an enantiotropic discophase (Dhd). The clearing points of the [Pd(CnO)4dpg}2] (n = 4, 8, 12) complexes are higher than those of the corresponding [Ni(CnO)4dpg}2] (n = 4, 8, 12) complexes. Interestingly, the [Pd(CnO)4dpg}2] complexes exhibit thermochromism and solvatochromism similar to that of [Ni(CnO)4dpg}2] complexes.

  双[1,2-双(3,4-二烷氧基苯基)乙二酮二氧亚氨]钯(II)配合物（缩写为[Pd(CnO)4dpg}2]；n = 1-12）已被合成并表征。研究发现，每个[Pd(CnO)4dpg}2]（n = 2-12）配合物都有一个对映盘相（Dhd）。Pd(CnO)4dpg}2]（n = 4、8、12）复合物的清点高于相应的[Ni(CnO)4dpg}2]（n = 4、8、12）复合物的清点。有趣的是，[Pd(CnO)4dpg}2] 复合物表现出的热致变色和溶致变色与[Ni(CnO)4dpg}2] 复合物相似。
• Discotic liquid crystals of transition metal complexes 25: influence of the central metal on columnar mesomorphism and π-acceptor properties of the octa-alkoxy-substituted bis(diphenyldithiolene)metal complexes
  作者：Kazuchika Ohta、Yoshio Inagaki-Oka、Hiroshi Hasebe、Iwao Yamamoto

  DOI：10.1016/s0277-5387(99)00356-3

  日期：2000.2

  In order to investigate the influence of the central metal on mesomorphism and a-acceptor properties of the octa-alkoxy-substituted metal complexes, novel homologs, bis [di(n-alkoxy)phenyldithiolene]palladium and bis[di(n-alkoxy)phenyldithiolene]platinum (n-alkoxy = CnH2n+1O, n = 1 to 12), have been synthesized. The mesophases were established by microscopic observations, DSC, and temperature-dependent X-ray diffraction techniques. As reported previously, the nickel complexes show a Col(h) mesophase for n = 5 to 12. On the other hand, the present palladium and platinum complexes show a Col(h) mesophase for n = 4 to 12 and n = 6 to 12, respectively. Thus, they give the Col(h) mesophase for a shorter length of alkoxy chain in the order Pd, Ni, Pt. For 6 less than or equal to n less than or equal to 12, the clearing points become higher in the order Pt < Ni < Pd. The intracolumnar stacking distances of these Ni, Pd and Pt complexes were observed at 3.64 +/- 0.02, 3.56 +/- 0.03, and 3.73 +/- 0.02 Angstrom, respectively. Thus, they gave a longer stacking distance in the order Pt > Ni > Pd. Hence, the order of stacking distances is apparently related to the order of clearing points. Moreover, the Pt, Ni and Pd complexes show reduction potentials at - 0.09 +/- 0.01, - 0.055 +/- 0.005, and 0.00 less than or equal to 0.01 V (versus SCE in CH2Cl2), respectively. They become better pi-acceptors in the order Pt < Ni < Pd. We reveal from the electronic absorption spectra that the LUMO energy level of these metal complexes decreases in the order Pt < Ni < Pd, and that the back donation of electrons from the central metal to the ligand occurs more in the same order Pt < Ni < Pd. This results in better a-acceptor properties in the order Pt < Ni < Pd for the present complexes. (C) 2000 Elsevier Science Ltd All rights reserved.