1,4-dibromo-2,5-dioctylbenzene | 117635-22-0

• 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: 1,4-dibromo-2,5-dioctylbenzene
• CAS: 117635-22-0
• 化学式: C₂₂H₃₆Br₂
• 分子量: 460.336
• InChiKey: NNODKPIGQMPPQW-UHFFFAOYSA-N

物化性质

• 沸点：
  471.1±40.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险性防范说明：
  P264,P280,P305+P351+P338,P337+P313
• 危险性描述：
  H319
• 储存条件：
  室温、密封、干燥

反应信息

• 作为反应物：
  描述：

  1,4-dibromo-2,5-dioctylbenzene 在 正丁基锂 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以78%的产率得到1-溴-2,5-二辛基-4-碘苯
  参考文献：
  名称：

  Synthesis, Light Harvesting, and Energy Transfer Properties of a Zinc Porphyrin Linked Poly(phenyleneethynylene)

  摘要：

  The synthesis of a zinc porphyrin linked conjugated homopolymer is presented. The synthetic strategy employed a directional polymerization of 1-iodo-2,5-dioctyl-4'-ethynyltolane in the presence of [10,20-bis(3,5-bis-tert-butylphenyll-5,15-diethynylporphinato]zinc(II) (12) or [10,20-bis(3,5-bis-tert-butylphenyl]-5,15-dibromoporphinatolzinc(II) (10). In the case of 12 the reaction was found to give a polymer product with a constant ratio of zinc porphyrin to incorporated monomer units regardless of the molecular weight. In the case of 10, however, the ratio of zinc porphyrin to incorporated monomer units decreased with increasing molecular weight of the polymer product. The polymer products were separated into fractions using preparative SEC. Studies of the energy transfer properties from the polymer to the zinc porphyrin revealed that there was little energy transfer in solution but quantitative energy transfer in the solid state. The polymer products proved difficult to handle in terms of device construction where a thin polymer film is sandwiched between two electrodes. We found this to be a consequence of the palladium catalysis employed during the polymerization. We finally discuss the issues concerning the problems with remnants from the Pd catalyst in the polymer samples and their removal.

  DOI：

  10.1021/ma048489u
• 作为产物：
  描述：

  1,4-二氯苯 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 溴 、 碘 作用下， 以 乙醚 为溶剂， 反应 48.0h， 生成 1,4-dibromo-2,5-dioctylbenzene
  参考文献：
  名称：

  A High-Yield Route to 2,5-Di-n-alkyl-1,4-benzenedicarboxylic Acids

  摘要：

  提供了一种简单且廉价的方法，以高产率制备先前未知的2,5-二正烷基对苯二甲酸5a-d。烷基链的长度可以轻松变化（n = 6, 8, 12, 16）。

  DOI：

  10.1055/s-1988-27583

文献信息

• Synthesis of an Acceptor–Donor–Acceptor Multichromophore Consisting of Terrylene and Perylene Diimides for Multistep Energy Transfer Studies
  作者：Sebastian Stappert、Chen Li、Klaus Müllen、Thomas Basché

  DOI：10.1021/acs.chemmater.5b04602

  日期：2016.2.9

  Motivated by the results obtained from the investigation of singlet–singlet annihilation in a linear multichromophore comprising terrylene diimides (TDI) and perylene diimide (PDI) in 2010, we report the detailed process toward the successful synthesis of a TDI–PDI–TDI dyad. Ineffective synthetic pathways, which were necessary for the understanding of the step-by-step construction of the complex multichromophore

  基于2010年在包含三甲苯二酰亚胺（TDI）和per二酰亚胺（PDI）的线性多发色团中单重态-单态an灭研究的结果，我们报告了成功合成TDI-PDI-TDI二聚体的详细过程。描述了无效的合成途径，这对于理解复杂的多色团的逐步构建是必需的，从而导致了通用的合成计划，涉及包含由刚性低聚亚苯基间隔基分隔的二甲苯二酰亚胺的多组分系统。
• The preparations and some properties of mixed aryl-thienyl oligomers and polymers
  作者：Andrew Pelter、Ieuan Jenkins、D.Elfyn Jones

  DOI：10.1016/s0040-4020(97)00629-7

  日期：1997.7

  The syntheses by transition metal coupling reactions of a large number of oligomers constructed from benzene and thiophene rings are described. The first use of arylcadmium chlorides for such coupling reactions is reported. The routes chosen allow for rational variation in the modes of linkage, the substitution and the proportions of the two units. The benzene and thiophene rings are always joined

  描述了通过过渡金属偶合反应合成由苯和噻吩环构成的大量低聚物。据报道，芳基氯化镉首次用于这种偶联反应。选择的途径允许在连接方式，取代和两个单元的比例方面进行合理的变化。苯环和噻吩环始终以已知顺序连接，并且可以带有各种规则间隔的官能团。另外，低聚物的形状可以任意改变。在所有情况下，碘或氯化铁的p型掺杂都会导致电导率大大提高。
• Synthesis and 2D self-assembly at the liquid–solid interface of novel H-bonding linear π-conjugated oligomers terminated by uracil and melamine units
  作者：G. Y. Y. Chng、X. Sun、S. J. Cho、D. Rajwar、A. C. Grimsdale、D. Fichou

  DOI：10.1039/c3nj01606d

  日期：——

  2D self-assembly of a novel π-conjugated oligomer terminated by two uracil units is solvent dependent and involves multiple intermolecular H-bonds.

  一个新型π共轭寡聚物在溶剂的作用下进行2D自组装，涉及多种分子间氢键。
• An Exceptional Red Shift of Emission Maxima upon Fluorine Substitution
  作者：Frederik C. Krebs、Holger Spanggaard

  DOI：10.1021/jo025592d

  日期：2002.10.1

  Compound 7 shows blue fluorescence with little solvent dependence (lambda(emission) = 410 nm in THF, CH2Cl2, and hexane), whereas compound 6 shows a highly solvent-dependent emission wavelength (lambda(emission) = 583 nm in THF, lambda(emission) = 560 nm in CH2Cl2, and lambda(emission) = 450 nm in hexane). The fluorescence red shift of compound 6 in a series of solvents with different polarity is discussed

  通过合成和两个同构供体-受体-供体染料分子的光物理特性，研究了全氟化对光物理性质的影响。介绍了两种通用的氟化苯化合物1,4-二氟-2,5-二全氟辛基苯（1）和1,4-二溴-2,5-二氟-3,6-二全氟辛基苯（2）的合成。已经确定了2的X射线结构，并且表明全氟辛基链以固态从苯环离析，从而产生了层状结构。使用4-甲酰基苯硼酸与（2）和1,4-二溴-2,5-二辛基苯（3）通过Suzuki偶联反应进一步合成，分别得到1,4''-diformyl-2'，5'-difluoro -3'，6'-二全氟辛基-对-亚苯基（4）和1,4''-二甲酰基-2'，5' -二辛基对-对亚苯基（5）。将二醛4和5与9,10-菲醌和碳酸氢铵在冰醋酸中缩合，得到染料分子1,4''-双（1H-菲[9,10-d]咪唑-2-基）-2 '，5'-二氟-3'，6'-二全氟辛基-对-亚联苯基（6）和1,4''-双（1H-菲[9,10-d]咪唑-2-基）-2'，
• Shadow Mask Templates for Site-Selective Metal Exchange in Magnesium Porphyrin Nanorings
  作者：Pernille S. Bols、Harry L. Anderson

  DOI：10.1002/anie.201804787

  日期：2018.6.25

  sites of demetalation when a magnesium porphyrin nanoring is treated with acid. Magnesium centers that are coordinated to the template are protected whereas uncoordinated magnesium centers are removed. After site‐selective demetalation, the template can be removed, and other cations, such as zinc(II) and copper(II), can be inserted into the free‐base porphyrin centers. This strategy provides a simple

  分子模板可以以多种不同的方式用于控制化学反应的结果。在此，我们提出了一种新型的模板导向合成。我们展示了模板可以用作荫罩：模板的形状会印在产品上，因为反应只发生在没有被模板掩盖的部位。当镁卟啉纳米环用酸处理时，我们通过使用寡吡啶模板来指示脱金属位点来证明这种效果。与模板配位的镁中心受到保护，而未配位的镁中心则被去除。位点选择性脱金属后，模板可以被去除，其他阳离子，如锌（II）和铜（II），可以插入游离碱卟啉中心。