1,5-diiodoanthracene | 161144-69-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,5-diiodoanthracene
• CAS: 161144-69-0
• 化学式: C₁₄H₈I₂
• 分子量: 430.027
• InChiKey: XHPOSPLNQDIFMW-UHFFFAOYSA-N

物化性质

• 熔点：
  236-238 °C
• 沸点：
  478.2±18.0 °C(Predicted)
• 密度：
  2.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,5-diiodoanthracene 在 甲醇 、 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 1,5-bis(ethynyl)anthracene
  参考文献：
  名称：

  Synthesis, Characterization, and Properties of Anthracene-Bridged Bimetallic Ruthenium Vinyl Complexes [RuCl(CO)(PMe₃)₃]₂(μ-CH═CH-anthracene-CH═CH)

  摘要：

  Four anthracene-based bimetallic ruthenium vinyl complexes, in which two ruthenium units are attached at different positions (the 9,10-, 1,5-, 2,6-, and 1,8-positions) of the anthracene moiety, have been synthesized by treating the appropriate anthracene-based ethynes with [RuHCl(CO)(PPh3)(3)]. These bimetallic complexes have been thoroughly characterized by NMR, X-ray diffraction, and elemental analysis. According to the single-crystal X-ray structures, the 2,6-disubstituted ruthenium vinyl complex has a more planar structure compared with the 9,10-disubstituted complex, possibly because it has less steric hindrance. Furthermore, we have investigated the optical electronic properties of these complexes, such as their UV/vis absorption spectra, fluorescence spectra, and electrochemical properties. The optical electronic results indicated that the 2,6-disubstituted ruthenium vinyl complex displayed the strongest fluorescence emission due to the more planar structure of its organic conjugated bridge, and the electrochemical studies showed that the two ruthenium centers displayed obvious differences in electronic communication when they are located at different positions on the anthracene unit, with the 9,10- and 1,8-disubstituted ruthenium vinyl complexes exhibiting better electronic communication and higher stability of the mixed-valence complex than the 1,5- and 2,6-disubstituted complexes.

  DOI：

  10.1021/om200622q
• 作为产物：
  描述：

  9,10-dihydro-9,10-dihydroxy-1,5-diiodoanthracene 在 苯肼 作用下， 以 溶剂黄146 为溶剂， 反应 7.0h， 以18%的产率得到1,5-diiodoanthracene
  参考文献：
  名称：

  Intramolecular Behaviors of Anthryldicarbenic Systems:  Dibenzo[b,f]pentalene and 1H,5H-Dicyclobuta[de,kl]anthracene

  摘要：

  9,10-Bis[methoxy(trimethylsilyl)methyl]anthracenes (24), synthesized from 9,10-dilithioanthracene (26) and bromomethoxytrimethylsilylmethane (27, 2 equiv), decompose (550-650 degreesC/10(-3) mmHg) carbenically to dibenzo[b,f]pentalene (28, > 48%). 9,10-Anthryldicarbenes 39 or their equivalents convert to pentalene 28 rather than di-peri-cyclobutanthracenes 30 and 31, benzobiphenylene 32, or extended rearrangement products 33-38. Formation of 28 from 24 raises questions with respect to the behavior of 1,3,4,6-cycloheptatetraenyl-1-carbenes 49, 2,4,5,7-cyclooctatetraenylidene 51, 2,5,7-cyclooetatriene-1,4-diylidene 52, 1,2,4,5,7-cyclooetapentaene 53, and bicyclo[4.1.0]heptatrienyl-1-carbenes 54 and to carbon-skeleton and hydrogen rearrangements of anthryldicarbenes 39 and/or their equivalents at various temperatures. 1,5-Bis [methoxy(trimethylsilyl)methyl] anthracenes (25), prepared from 1,5-diiodoanthracene (63) and methoxytrimethylsilylmethylzinc bromide (57,2 equiv) as catalyzed by PdCl2(PPh3)(2), yield the di-peri-carbenic reaction product 1H,5H-dicyclobuta[de,kl]-anthracene (30, > 40%) on pyrolysis at 550-650 degreesC/10(-3) mmHg. Proof of structure and various aspects of the mechanisms of formation of 30 are discussed.

  DOI：

  10.1021/jo010404p

文献信息

• Effects of backbone substituent and intra-ligand hydrogen bonding interaction on ethylene polymerizations with α-diimine nickel catalysts
  作者：Liu Zhong、Cheng Du、Guangfu Liao、Heng Liao、Handou Zheng、Qing Wu、Haiyang Gao

  DOI：10.1016/j.jcat.2019.05.026

  日期：2019.7

  for olefin polymerization have received substantial attention in the field of polyolefin research. In this paper, we initially reported backbone substituent effects on ethylene polymerizations with α-diimine nickel catalysts and intra-ligand hydrogen bonding interactions operating ethylene polymerizations. A series of α-diimine nickel catalysts with electron-donating/withdrawing groups (OMe, H, Cl

  在聚烯烃研究领域中，过渡金属催化剂的设计和用于烯烃聚合的新的催化剂设计策略的发展已受到了广泛的关注。在本文中，我们最初报道了主链取代基对使用α-二亚胺镍催化剂的乙烯聚合反应以及在乙烯聚合反应中进行的配体内氢键相互作用的影响。合成了一系列在二苯并桶烯骨架上带有给电子/吸电子基团（OMe，H，Cl，Br和I）的α-二亚胺镍催化剂，并将其用于乙烯聚合。卤素取代基同时对乙烯聚合和催化剂5表现出空间和电子效应具有二碘（I）取代基的化合物显示出最高的活性并产生最高的分子量的聚乙烯。帧内配体的氢键相互作用（C ħ... OME）在甲氧基取代的最初观察dibenzobarrelene α二亚胺镍络合物，和弱非共价相互作用在高温下增强了乙烯聚合的催化剂的热稳定性和生活时尚到80°C。
• Chemistry of Anthracene–Acetylene Oligomers XV. Synthesis, Structures, and Dynamic Behavior of Chiral Anthrylene–Ethynylene Cyclic Tetramers and Related Derivatives and Resolution of Enantiomers
  作者：Takeharu Ishikawa、Toshiaki Shimasaki、Haruo Akashi、Tetsuo Iwanaga、Shinji Toyota、Mikio Yamasaki

  DOI：10.1246/bcsj.20090270

  日期：2010.3.15

  A cyclic arylene–ethynylene tetramer with a 1,5-anthrylene unit and a cramp moiety consisting of three anthrylene units and its derivatives with a 1,4-phenylene, 1,5-naphthylene, or 2,6-di-t-butyl-...

  环状亚芳基-亚乙炔四聚体，带有一个 1,5-亚蒽单元和一个由三个亚蒽单元及其衍生物和一个 1,4-亚苯基、1,5-亚萘基或 2,6-二叔丁基组成的痉挛部分- ...
• Chemistry of Anthracene–Acetylene Oligomers. XVIII. Construction and Structures of Belt-Shaped Macrocyclic Oligomers with Anthracene Units and Acetylene Linkers and Resolution of Chiral Derivatives
  作者：Takeharu Ishikawa、Tetsuo Iwanaga、Shinji Toyota、Mikio Yamasaki

  DOI：10.1246/bcsj.20110066

  日期：2011.7.15

  Acyclic anthracene–acetylene trimers consisting of two 1,8-anthrylene units and one 1,5- or 1,8-anthrylene unit were cyclized by Eglinton coupling to form the corresponding cyclic trimer, hexamer, ...

  由两个1,8-蒽单元和一个1,5-或1,8-蒽单元组成的无环蒽-乙炔三聚体通过Eglinton偶联环化形成相应的环状三聚体、六聚体、...
• Triptycene: No Homoconjugation Effect for Extending Optical Properties of π-Conjugated Oligomers
  作者：Xingwei Gu、Yee-Hing Lai

  DOI：10.1021/ol102147f

  日期：2010.11.19

  extended conjugation in the triptycene pair. The electronic spectra of the triptycene and dihydroanthracene pairs are in fact superimposable. There is definite evidence that triptycene displays zero homoconjugation effect.

  合成了1,5-和1,8-双（联芴基）蒽，并将其转化为相应的双（联芴基）三联蒽和双（联芴基）-9,10-二氢蒽。对它们的光学性质的分析表明，在三并茂对中没有延长共轭的特征。实际上，三萜和二氢蒽对的电子光谱是可叠加的。有确凿的证据表明三萜类化合物显示出零的共轭效应。
• [EN] ORGANIC COMPOUND, ORGANIC ELECTROLUMINESCENT DEVICE, AND ELECTRONIC APPARATUS<br/>[FR] COMPOSÉ ORGANIQUE, DISPOSITIF ÉLECTROLUMINESCENT ORGANIQUE, ET APPAREIL ÉLECTRONIQUE<br/>[ZH] 有机化合物、有机电致发光器件和电子装置
  申请人：SHAANXI LIGHTE OPTOELECTRONICS MAT CO LTD

  公开号：WO2021135183A1

  公开（公告）日：2021-07-08

  本申请属于有机材料技术领域，提供了一种有机化合物，将金刚烷螺芴基团和蒽基基团连接组合，得到了一种用于有机电致发光器件的新型化合物。该化合物中，金刚烷螺芴中金刚烷通过超共轭效应大幅增加芴基上的电子云密度，使化合物HOMO能级变浅，空穴迁移能力提升，金刚烷螺芴和蒽基基团均具有高的空穴迁移率，将二者连接时，使得分子整体的空穴迁移率进一步提高，有利于降低器件工作电压并提升发光效率。本申请还提供包含所述化合物的电子元件和电子装置，该有机化合物能够改善电子元件的性能。