1,2-bis(4-(decyloxy)phenyl)ethane-1,2-dione | 156733-59-4

• 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(4-(decyloxy)phenyl)ethane-1,2-dione
• 英文别名: 4,4'-bis(decyloxy)benzil；4, 4'-didecyloxy-benzil；4,4'-di(decanoxy)benzil；1,2-Bis(4-decyloxyphenyl) ethane-1,2-dione；1,2-bis(4-decoxyphenyl)ethane-1,2-dione
• CAS: 156733-59-4
• 化学式: C₃₄H₅₀O₄
• 分子量: 522.769
• InChiKey: XAKROHBLNSTBJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  38
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-bis(4-(decyloxy)phenyl)ethane-1,2-dione 在 N-碘代丁二酰亚胺 、 三氟乙酸 作用下， 反应 3.5h， 以88%的产率得到3,3'-diiodo-4,4'-bis(decyloxy)benzil
  参考文献：
  名称：

  盘状镍双（二硫烯）配合物 - 合成、光电化学和介晶性质

  摘要：

  15 种中性长链取代的盘状镍双（1,2-二苯基-1,2-乙烯二硫烯）配合物 [Ni(dpedt)2]，包括 13 种新化合物，已通过新的短而有效的合成途径合成。物理研究表明，这些配合物是热稳定的，具有良好的电子接受性能，并在近红外光谱区强烈吸收光。[Ni(dpedt)2] 的电化学和光学性质适度取决于连接到配合物苯环上的官能团。它们的 LUMO 和 HOMO 能级分别在 –4.7 至 –5.0 和 –5.7 至 –6.0 eV 的范围内。两个八(n-烷氧基)-取代的配合物表现出具有六方对称性的柱状液晶相。

  DOI：

  10.1002/ejic.201001288
• 作为产物：
  描述：

  在 selenium(IV) oxide 、 硫酸 、 溶剂黄146 作用下， 生成 1,2-bis(4-(decyloxy)phenyl)ethane-1,2-dione
  参考文献：
  名称：

  Discotic liquid crystals of transition metal complexes, 31: establishment of mesomorphism and thermochromism of bis[1,2-bis(4-n-alkoxyphenyl)ethane-1,2-dithiolene]nickel complexes

  摘要：

  两系列双[1,2-双(4-正烷基苯基)乙烷-1,2-二硫醇]镍，Cn–Ni（n=1–12），和双[1,2-双(4-正烷氧基苯基)乙烷-1,2-二硫醇]镍，CnO–Ni（n=1–12, 14, 16, 18）已被合成。通过使用不同的扫描量热法、偏光显微镜、温度依赖性X射线衍射技术、电子光谱和循环伏安法，研究了它们的介晶性、热变色性、超分子结构和π受体性质。从X射线衍射和电子光谱结果来看，确定了CnO–Ni 复合物对于 n≤10 展现两种不同颜色的盘状层状（DL）介晶相，而 Cn–Ni 复合物均无介晶相，并且热变色性（棕色→绿色）归因于从 Ni–Ni 键合二聚体到 Ni–S 键合二聚体的缓慢转变。

  DOI：

  10.1039/b007135h

文献信息

• “Flexiball” Toolkit:  A Modular Approach to Self-Assembling Capsules
  作者：Brendan M. O'Leary、Tomas Szabo、Niels Svenstrup、Christoph A. Schalley、Arne Lützen、Mathias Schäfer、Julius Rebek

  DOI：10.1021/ja011651d

  日期：2001.11.1

  We report the synthesis and characterization of new, self-assembling molecular capsules. The modular strategy makes use of glycoluril building blocks available in multigram amounts combined with aromatic spacer elements. The lengthy syntheses encountered with earlier generations of capsules are avoided, and several capsules of nanometer dimensions are now accessible. Single bond attachments between

  我们报告了新的自组装分子胶囊的合成和表征。模块化策略利用与芳香族间隔元素相结合的多克量的甘脲结构单元。避免了早期胶囊遇到的冗长合成，现在可以使用几个纳米尺寸的胶囊。间隔物和甘脲模块之间的单键连接导致单体作为二聚体胶囊，其刚性低于早期对应物。使用 NMR 和 ESI 质谱的组合研究了同源和异源二聚体胶囊的主客体特性。它们对不同尺寸的客人表现出不太明显的选择性，并且当中央间隔单元上没有刚性元件时，它们增加的灵活性可以防止自组装。一些新胶囊带有向内定向的仲酰胺 NH 质子。这些可以进一步官能化，如它们的甲基化所示，得到叔类似物。这些结构对于在凹分子表面上放置官能团具有更广泛的意义。
• Discotic liquid crystals of transition metal complexes. Part 26: Supramolecular structures of long­chain­substituted octaphenyltetrapyrazinoporphyrazine derivatives
  作者：Kazuchika Ohta、Satoru Azumane、Wataru Kawahara、Nagao Kobayashi、Iwao Yamamoto

  DOI：10.1039/a905538j

  日期：——

  Ten novel columnar liquid crystals, [octakis(4-alkoxyphenyl)tetrapyrazinoporphyrazinato]metal(II) (abbreviated as (C n O) 8 –M; n = 10, 12; M = Cu, Ni) and [octakis(3,4-dialkoxyphenyl)tetrapyrazinoporphyrazinato]metal(II) (abbreviated as (C n O) 16 –M; n = 8, 10, 12; M = Cu, Ni), have been synthesized and characterized. It was found that the mesophase structures of (C n O) 8 –M are very sensitive to the central metal and closely related to the aggregate structures in the solution. The (C n O) 16 –M derivatives exhibit a D hd mesophase at lower temperatures and a D rd (C2/m) phase at higher temperatures. Thus, the mesophase with higher symmetry appears at lower temperatures for these (C n O) 16 –M derivatives. This is quite opposite to the general tendency for the higher symmetry mesophase to appear at higher temperatures. In order to further clarify the structures of both the mesophases and the aggregate in solutions, the electronic and magnetic circular dichromism (MCD) spectra were measured. The Q band of (C n O) 16 –M in n-hexane showed a wide Davidov splitting. It was proven that such a wide splitting of the Q band can be attributed to the formation of dimers. The dimerization was confirmed by vapor pressure osmometric (VPO) measurements in n-hexane solution. Furthermore, the spectrum of the thin film in the mesophase in the absence of solvent at room temperature was similar to that of then-hexane solution. From these electronic absorption spectra, MCD spectra, VPO measurements and temperature-dependent X-ray diffraction studies, it was clarified for (C n O) 16 –M that the dimer structure in n-hexane solution is closely related to those in the thermotropic mesophases.

  十种新型柱状液晶，[八烷基（4-烷氧基苯基）四吡嗪卟嗪]金属（II）（缩写为 (C n O) 8 -M；n = 10，12；M = Cu、Ni）和[八(3,4-二烷氧基苯基)四吡嗪卟嗪]金属（II）（缩写为 (C n O) 16 -M；n = 8、10、12；M = Cu、Ni）的合成和表征。研究发现，(C n O) 8 -M的介相结构对中心金属非常敏感，并与溶液中的聚合体结构密切相关。(C n O) 16 -M 衍生物在较低温度下表现出 D hd 介相，在较高温度下表现出 D rd（C2/m）相。因此，这些 (C n O) 16 -M 衍生物在较低温度下会出现对称性较高的介相。这与较高对称性介相在较高温度下出现的一般趋势截然相反。为了进一步弄清介相和聚合体在溶液中的结构，我们测量了电子和磁性圆重铬（MCD）光谱。(C n O) 16 -M 在正己烷中的 Q 波段显示出很宽的戴维夫分裂。实验证明，Q 波段出现如此宽的分裂是因为形成了二聚体。在正己烷溶液中进行的蒸气压渗透压（VPO）测量证实了二聚体的形成。此外，在室温下无溶剂介相薄膜的光谱与当时正己烷溶液的光谱相似。通过这些电子吸收光谱、MCD 光谱、VPO 测量和温度相关的 X 射线衍射研究，可以明确 (C n O) 16 -M 在正己烷溶液中的二聚体结构与热致性介相中的二聚体结构密切相关。
• Heteroleptic Bis(<i>cis</i>-1,2-disubstituted ethylene-1,2-dithiolato)nickel Complexes Obtained by Ligand-Exchange Reaction: Synthesis and Properties
  作者：Thi Minh Ha Vuong、Thanh-Tuan Bui、Alix Sournia-Saquet、Alain Moreau、Kathleen I. Moineau-Chane Ching

  DOI：10.1021/ic402528j

  日期：2014.3.17

  to synthesize nickel bis(dithiolene) complexes bearing one hydroxyl functional group aimed at being grafted thereafter onto polymer materials. This reaction leads easily to heteroleptic complexes with the ethylene-1,2-dithiolato core substituted by either alkyl or aryl moieties. Details on synthetic parameters are given. A direct link between the electronic properties of the obtained molecules and

  已经研究了配体交换反应以合成带有一个羟基官能团的镍双（二硫代烯）镍配合物，该配合物旨在随后被接枝到聚合物材料上。该反应容易导致杂芳族配合物，其被烷基或芳基部分取代的乙烯-1,2-二硫代巯基核心。给出了综合参数的详细信息。突出显示了所得分子的电子性质与参与配体交换反应的母体配合物的电子性质之间的直接联系，也表明该反应是制备具有量身定制的前沿轨道能量的镍配合物的有效方法。
• Pyrazine-Containing Acene-Type Molecular Ribbons with up to 16 Rectilinearly Arranged Fused Aromatic Rings
  作者：Baoxiang Gao、Ming Wang、Yanxiang Cheng、Lixiang Wang、Xiabin Jing、Fosong Wang

  DOI：10.1021/ja800311a

  日期：2008.7.1

  A series of acene-type conjugated molecules (1-5) containing 2-6 pyrazine units and up to 16 rectilinearly arranged fused aromatic rings were synthesized by condensation coupling of 1,2-diamines and 1,2-diketones. The energy gap of the molecules estimated from absorption edge decreases with an increase in molecular length, indicating the well-delocalized nature of the molecules. The cyclic voltammetry

  通过1,2-二胺和1,2-二酮的缩合偶联合成了一系列含有2-6个吡嗪单元和多达16个直线排列的稠合芳环的并苯型共轭分子(1-5)。从吸收边估计的分子能隙随着分子长度的增加而减小，表明分子的良好离域性质。循环伏安测量表明这些带状吡嗪衍生物的 n 型性质取决于分子长度和吡嗪单元的数量。随着吡嗪单元的数量和分子长度的增加，第一个还原波开始从 -1.16 到 -0.62 V（相对于 Ag/AgCl），分别对应于 -3.24 和 -3.78 eV 的 LUMO 能级。随着分子长度的增加，这些分子在溶液中更容易聚集，如 (1) H NMR 和 UV-vis 吸收光谱所示。在芘单元中引入叔丁基可以显着抑制这些分子在溶液中的聚集。高电子亲和力、高环境稳定性和易于结构修饰使这些化合物成为一类新型 n 型半导体的优秀候选者。
• Three donor-acceptor polymeric electrochromic materials employing 2,3-bis(4-(decyloxy)phenyl)pyrido[4,3-b]pyrazine as acceptor unit and thiophene derivatives as donor units
  作者：Hui Zhao、Yuanyuan Wei、Jinsheng Zhao、Min Wang

  DOI：10.1016/j.electacta.2014.09.022

  日期：2014.11

  In this study, 5,8-dibromo-2,3-bis(4-(decyloxy) phenyl) pyrido[4,3-b]pyrazine was synthesized and used as the acceptor unit, which then be coupled with three thiophene derivatives (3-methylthiophen, 3-methoxythiophen and 3,4-dimethoxythiophen) to give rise to three novel monomers, 2,3-bis(3-methoxythiophen and 3,4-dimethoxythiophen) to give rise to three novel monomers, 2,3-bis (4-decyloxy) phenyl)-5,8-bis(3-methylthiophen-2-yl) pyrido[4,3-b]pyrazine(M1), 2,3-bis(4-decyloxy) phenyl)-5,8-bis(3-methoxylthiophen-2-yl) pyrido[4,3-b]pyrazine (M2) and 2,3-bis(4-decyloxy) phenyl)5,8-bis(3,4-dimethoxylthiophen-2-yl) pyrido [4,3-b]pyrazine(M3). The corresponding polymers P1, P2, P3 were obtained by electropolymerization method. These polymers were characterized in terms of their spectroelectrochemical and electrochemical properties by cyclic voltammetry and UV-Vis-NIR spectroscopy. The band gaps of the polymers were calculated based on the spectroelectrochemistry analysis, and were 1.39 eV, 1.136 eV and 1.25 eV for P1, P2, P3, respectively. Electrochromic investigations showed that P1 switched between blue and colorless transmissive state, P2 switched between green to transmissive light gray color, and P3 switched between blue to transmissive light brown color. Electrochromic switching studies showed that all three polymers exhibit high coloration efficiency, fast response time, and express more than 45% change in the transmittance in the near-IR region, which could make these polymers useful in applications in NIR electrochromic devices. (C) 2014 Elsevier Ltd. All rights reserved.