bis(4-octylphenyl)methanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis(4-octylphenyl)methanone
• 化学式: C₂₉H₄₂O
• 分子量: 406.652
• InChiKey: NRMLGIJGBUYWLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  30
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  bis(4-octylphenyl)methanone 在 正丁基锂 、 ammonium cerium (IV) nitrate 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.0h， 生成 1-phenylethnyl-2-di(p-octylphenyl)methoxymethylbenzene
  参考文献：
  名称：

  Carbon-Bridged Oligo(phenylenevinylene)s: Stable π-Systems with High Responsiveness to Doping and Excitation

  摘要：

  The high responsiveness of pi-conjugated materials to external stimuli, such as electrons and photons, accounts for both their utility in optoelectronic applications and their chemical instability. Extensive studies on heteroatom-stabilized pi-conjugated systems notwithstanding, it is still difficult to combine high performance and stability. We report here that carbon-bridged oligo(p-phenylenevinylene)s (COPV-n) are not only more responsive to doping and photoexcitation but also more stable than the conventional p-phenylenevinylenes and poly(3-hexylthiophene), surviving photolysis very well in air, suggesting that they could serve as building blocks for optoelectronic applications. Activation of the ground state by installation of bond angle strain toward the doped or photoexcited state and the flat, rigid, and hindered structure endows COPVs with stimuli-responsiveness and stability without recourse to heteroatoms. For example, COPV-6 can be doped with an extremely small reorganization energy and form a bipolaron delocalized over the entire it system. Applications to bulk and molecular optoelectronic devices are foreseen.

  DOI：

  10.1021/ja309318s
• 作为产物：
  描述：

  4,4'-二溴二苯甲酮 在 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 bis(4-octylphenyl)methanone
  参考文献：
  名称：

  Air- and Heat-Stable Planar Tri-p-quinodimethane with Distinct Biradical Characteristics

  摘要：

  A heptacyclic carbocycle possessing three p-quinodimethane units conjugated in one plane has been synthesized and shown to exhibit distinct biradical characteristics. The molecule has a HOMO/LUMO band gap of ca. 1 eV and a S(0)-T(1) energy gap of 2.12 kcal/mol, and it absorbs and emits near-IR light at room temperature. It is air-stable under ambient light for several months and thermally stable up to 160 degrees C under nitrogen, and it undergoes reversible two-electron oxidation and reduction. The synthetic approach is such that a smaller and larger oligo-p-quinodimethane can be synthesized.

  DOI：

  10.1021/ja206060n

文献信息

• B/N-Doped <i>p</i>-Arylenevinylene Chromophores: Synthesis, Properties, and Microcrystal Electron Crystallographic Study
  作者：Hua Lu、Takayuki Nakamuro、Keitaro Yamashita、Haruaki Yanagisawa、Osamu Nureki、Masahide Kikkawa、Han Gao、Jiangwei Tian、Rui Shang、Eiichi Nakamura

  DOI：10.1021/jacs.0c10337

  日期：2020.11.4

  Linearly conjugated systems have long served as an archetype of conjugated materials, but suffer from two intrinsic structural problems: potential instability due to intermolecular interactions and the flexibility of the C-C bonds connecting C═C bonds. Efforts to solve these problems have included the insertion of aromatic units as a part of the conjugation and the introduction of carbon bridges to

  线性共轭体系长期以来一直是共轭材料的原型，但存在两个固有的结构问题：分子间相互作用导致的潜在不稳定性和连接 C=C 键的 CC 键的灵活性。解决这些问题的努力包括插入芳香单元作为共轭的一部分和引入碳桥以阻止键旋转。我们在此报告了通过将环戊二烯 [c][1,2] 氮杂硼骨架作为共轭系统的一部分并入合成的 B/N 掺杂对亚芳基亚乙烯基发色团。这种新骨架固有的环应变既使共轭变平，又使共轭硬化，并且 B--N+ 配键比 CC 键更容易形成，这简化了合成设计。BN 配键也减少了 HOMO-LUMO 间隙，因此，与它们的全碳同系物相比，吸收和发射发生显着红移，同时在溶液和薄膜状态下保持高光稳定性和高荧光量子产率。双 B/N 掺杂化合物在 540 nm 处显示发射峰，斯托克斯位移为 20 nm，荧光量子产率为 98%。这些分子可作为用于活细胞成像的优良亲脂荧光染料，表现出比市售 BODIPY 染料更高的光稳定性。双
• Three-Dimensionally Homoconjugated Carbon-Bridged Oligophenylenevinylene for Perovskite Solar Cells
  作者：Qifan Yan、Yunlong Guo、Anna Ichimura、Hayato Tsuji、Eiichi Nakamura

  DOI：10.1021/jacs.6b04002

  日期：2016.8.31

  Stabilization of the radical cationic state of a donor molecule by 3-D homoconjugation was probed using a substituted carbon-bridged oligophenylenevinylene backbone (COPV, or 5,5-diarylindeno[2,1-a]indenes). For molecules bearing electron-donating groups as the 5,5-aryl moieties, a one-electron oxidation of the COPV backbone results in delocalization of the cationic charge over the whole molecule with

  使用取代的碳桥联低聚亚苯基亚乙烯基主链（COPV，或 5,5-二芳基茚并 [2,1-a] 茚）探测了通过 3-D 同共轭稳定供体分子的自由基阳离子状态。对于带有供电子基团作为 5,5-芳基部分的分子，COPV 主链的单电子氧化导致整个分子上的阳离子电荷离域，重组能量很小。通过 3-D 同共轭形成稳定自由基阳离子的化合物产生均匀的非晶薄膜，并显示出高短路电流、高填充因子，因此当用作有机 - 无机杂化物的空穴传输层时具有高功率转换效率铅钙钛矿太阳能电池。因此，这种材料在空气中的性能和稳定性与使用基准材料获得的性能和稳定性相当，
• Bis(aminoaryl) Carbon-Bridged Oligo(phenylenevinylene)s Expand the Limits of Electronic Couplings
  作者：Paula Mayorga Burrezo、Nai-Ti Lin、Koji Nakabayashi、Shin-ichi Ohkoshi、Eva M. Calzado、Pedro G. Boj、María A. Díaz García、Carlos Franco、Concepciò Rovira、Jaume Veciana、Michael Moos、Christoph Lambert、Juan T. López Navarrete、Hayato Tsuji、Eiichi Nakamura、Juan Casado

  DOI：10.1002/anie.201610921

  日期：2017.3.6

  Carbon‐bridged bis(aminoaryl) oligo(para‐phenylenevinylene)s have been prepared and their optical, electrochemical, and structural properties analyzed. Their radical cations are class III and class II mixed‐valence systems, depending on the molecular size, and they show electronic couplings which are among the largest for the self‐exchange reaction of purely organic molecules. In their dication states

  制备了碳桥联的双（氨基芳基）低聚（对-亚苯基亚乙烯基），并分析了它们的光学，电化学和结构性质。它们的自由基阳离子是III类和II类混合价体系，具体取决于分子大小，并且它们显示出电子偶联，在纯有机分子的自交换反应中是最大的。在其指示状态下，反铁磁耦合的大小逐渐从quinoidal闭合壳到open-shell双自由基。数据证明，自由基阳离子中的电子耦合和指示剂中的单线态-三重态间隙显示出相似的小衰减因子，因此允许电荷/自旋在相当长的距离上转移。
• Muraoka,M. et al., Chemical and pharmaceutical bulletin, 1960, vol. 8, p. 860 - 866
  作者：Muraoka,M. et al.

  DOI：——

  日期：——
• Synthesis of alkyl- and alkoxy-substituted benzils and oxidative coupling to tetraalkoxyphenanthrene-9,10-diones
  作者：Bernhard Mohr、Volker Enkelmann、Gerhard Wegner

  DOI：10.1021/jo00082a022

  日期：1994.2

  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.