2-bromo-1,4-bis(octyloxy)benzene | 194204-71-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-bromo-1,4-bis(octyloxy)benzene
• 英文别名: 1-Bromo-2,5-dioctyloxybenzene；2-bromo-1,4-dioctoxybenzene
• CAS: 194204-71-2
• 化学式: C₂₂H₃₇BrO₂
• 分子量: 413.439
• InChiKey: LARBGUVIUTUZSN-UHFFFAOYSA-N

物化性质

• 沸点：
  460.9±25.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-1,4-bis(octyloxy)benzene 在 四(三苯基膦)钯 氢氧化钾 、 copper(l) iodide 、 硫酸 、 溶剂黄146 、 二异丙胺 、 pyridinium chlorochromate 、 sodium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 46.5h， 生成 1,4-bis(4-formyl-2,5-dioctyloxyphenyl)butadiyne-1,3
  参考文献：
  名称：

  Supramolecular Ordering, Thermal Behavior, and Photophysical, Electrochemical, and Electroluminescent Properties of Alkoxy-Substituted Yne-Containing Poly(phenylene−vinylene)s

  摘要：

  Alkoxy-substituted and defect-free yne-containing poly(phenylene-vinylene)s, 15a-d, having the general constitutional unit (-Ph-CdropC-Ph-CH=CH-Ph-CH=CH-) synthesized through the olefination reactions of the fluorophoric dialdehyde 7 [1,2-bis(4-formyl-2,5-dialkoxyphenyl)acetylene] with various 2,5-dialkoxy-p-xylylenebis(diethylphosphonates), 14a-d, are reported. A new synthetic route to 1-bromo-2,5-dialkoxybenzaldehyde (starting material for the synthesis of 7) allowing the grafting of all types of alkoxy side chains is also reported. Bulk state properties of the four polymeric materials have been analyzed using various experimental methods giving information on the thermal behavior as well as self-assembling morphologies at different size scales. Crystalline superstructures of either spherulitic or rodlike morphology, comprised of polymeric backbone layers separated by the side chains are identified to develop by nucleation and growth process for symmetrically alkoxy substituted 15a-c. Discrepancy between optical (E-g(opt)) and electrochemical (E-g(ee)) band gaps was observed to be dependent on the bulkiness (15c) and length (15b) of the grafted side chains. Octadecyloxy side chains in 15b not only lead to well structured photoluminescence and electroluminescence spectra and higher fluorescence quantum yields but also allow the design of LED-devices of the configuration ITO/PEDOT/polymer/Ca with improved parameters (eta(ext) = 2.15%, luminance = 5760 cd/m(2)) relative to the octyloxy-substituted polymer 15a (eta(ext) = 0.79%, luminance = 1406 cd/m(2)). Despite the differences in the conjugation pattern between polymers 15 and polymers 17 [(-Ph-CdropC-Ph-CdropC-Ph-CH=CH-Ph-CH=CH-)], an identical chromophore system of structure Ph-CdropC-Ph-CH=CH-Ph-CH=CH-Ph-CdropC-Ph was found to be responsible for their emissive behavior as confirmed by fluorescence kinetics measurements (tau, k(f), k(nr)) and quantum chemical calculations. The differences observed in their solid-state photophysical properties are ascribed to the combined effects of the backbone rigidity (as a function of the number of -CdropC- moieties in the repeating unit) and the nature of the side chains. Moreover less -CdropC- units within polymers 15 lead to the more than 100-fold improvement of their electroluminescent parameters compared to polymers 17.

  DOI：

  10.1021/ma0488111
• 作为产物：
  描述：

  1-溴辛烷 在 N-溴代丁二酰亚胺(NBS) 、 四丁基溴化铵 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-bromo-1,4-bis(octyloxy)benzene
  参考文献：
  名称：

  聚合物太阳能电池用三苯并二恶嗪基共轭聚合物的合成及性能

  摘要：

  作为稠环共轭单元，三苯二恶嗪已应用于聚合物太阳能电池的两系列无噻吩共轭聚合物中。聚合物是通过多步合成路线合成的，取代基对反应物的反应性有很大的影响。通过实验数据分析和理论模拟，详细研究了聚合物结构之间的关系以及热，光学和电化学性能。该聚合物具有高度平坦的骨架，宽的Vis / NIR吸收带，合适的前沿分子轨道能以及1.3至1.8 eV的低带隙。他们的光伏器件的功率转换效率约为1％。

  DOI：

  10.1002/ejoc.201700393

文献信息

• A Molecular Replication Process Drives Supramolecular Polymerization
  作者：Yuanning Feng、Douglas Philp

  DOI：10.1021/jacs.1c06404

  日期：2021.10.20

  Supramolecular polymers are materials in which the connections between monomers in the polymer main chain are non-covalent bonds. This area has seen rapid expansion in the last two decades and has been exploited in several applications. However, suitable contiguous hydrogen-bond arrays can be difficult to synthesize, placing some limitations on the deployment of supramolecular polymers. We have designed

  超分子聚合物是聚合物主链中单体之间的连接为非共价键的材料。在过去的二十年里，这一领域得到了迅速的发展，并在多种应用中得到了利用。然而，合适的连续氢键阵列可能难以合成，这对超分子聚合物的部署造成了一些限制。我们设计了一种由双功能单体组装而成的氢键聚合物，该双功能单体由两个由刚性间隔物隔开的复制模板组成。这种设计允许通过复制器的自模板特性自动催化形成聚合物主链，并从溶液中的组成成分驱动双功能单体的合成。模板导向 1, 硝酮和马来酰亚胺之间的 3-偶极环加成反应以高非对映选择性进行，得到双功能单体。允许双功能单体在溶液中聚合的自互补复制模板之间的高结合亲和力源自与该结合过程相关的正协同性。已经通过扩散有序核磁共振光谱研究了聚合物在溶液中的组装。聚合物材料的微晶和薄膜都可以很容易地制备，并且已经通过粉末 X 射线衍射和扫描电子显微镜进行了表征。
• A Highly Selective Catalytic System for the Cross-Coupling of (<i>E</i>)-Styryl Bromide with Benzeneboronic Acid: Application to the Synthesis of All-Trans Poly(arylenevinylene)s
  作者：Masayuki Wakioka、Yuichiro Mutoh、Ryo Takita、Fumiyuki Ozawa

  DOI：10.1246/bcsj.82.1292

  日期：2009.10.15

  A highly selective system for palladium-catalyzed polycondensation of (E,E)-1,4-bis(2-bromoethenyl)benzene ((E,E)-1) with 2,5-dioctyloxybenzene-1,4-diboronic acid (2a) to give all-trans poly[( p-phenylenevinylene)-alt-(2,5-dioctyloxy-1,4-phenylenevinylene)] (all-trans 3) has been investigated using (E)-styryl bromide ((E)-4) and 2,5-dioctyloxybenzeneboronic acid (5a) as model compounds of (E,E)-1 and 2a, respectively. The reaction of (E)-4 and 5a in toluene in the presence of Pd(PPh3)4 catalyst and aqueous K2CO3 base affords considerable amounts of homocoupling products (i.e., 1,4-diphenylbutadiene (13%) and 2,2′,5,5′-tetraoctyloxybiphenyl (22%)), together with (E)-2,5-dioctyloxystilbene ((E)-6a) as the cross-coupling product (30%). The use of aqueous NaOH as a strong base and Bu4NBr as a phase-transfer catalyst notably reduces the homocoupling products, and the use of Pd(PBut3)2 instead of Pd(PPh3)4 results in almost perfect selectivity of the cross-coupling product (E)-6a. Under optimized catalytic conditions, the desired all-trans 3 has been successfully prepared without notable defects in the polymer chain.

  使用(E)-苯乙烯溴化物((E)-4)和 2,5-二辛基氧基-1,4-苯乙烯(2a)，研究了钯催化(E,E)-1,4-双(2-溴乙烯基)苯((E,E)-1)与 2,5-二辛基氧基-1,4-苯二硼酸(2a)缩聚得到全反式聚[( 对苯基乙烯)-alt-(2、(E)-苯乙烯溴化物（(E)-4）和 2,5-二辛基氧基苯硼酸（5a）分别作为 (E,E)-1 和 2a 的模型化合物，研究了全反式聚[( 对亚苯基乙烯)-alt-(2,5-二辛基氧基-1,4-亚苯基乙烯)]（全反式 3）。在 Pd(PPh3)4 催化剂和 K2CO3 水基存在下，(E)-4 和 5a 在甲苯中发生反应，生成大量的均偶联产物（即、1,4-二苯基丁二烯（13%）和 2,2′,5,5′-四辛基氧基联苯（22%）），以及作为交叉偶联产物的 (E)-2,5- 二辛基氧基二苯乙烯（(E)-6a）（30%）。使用 NaOH 水溶液作为强碱和 Bu4NBr 作为相转移催化剂可以显著减少同偶联产物，而使用 Pd(PBut3)2 而不是 Pd(PPh3)4，可以几乎完全选择性地得到交叉偶联产物 (E)-6a。在优化的催化条件下，成功制备出了所需的全反式 3，聚合物链中没有明显的缺陷。
• Comprehensive Analysis of Fragment Orbital Interactions to Build Highly π-Conjugated Thienylene-Substituted Phenylene Oligomers
  作者：Jean-Charles Florès、Marie-Agnès Lacour、Xavier Sallenave、Françoise Serein-Spirau、Jean-Pierre Lère-Porte、Joël J. E. Moreau、Karinne Miqueu、Jean-Marc Sotiropoulos、David Flot

  DOI：10.1002/chem.201203869

  日期：2013.6.3

  π‐Conjugated thienylenephenylene oligomers with fluorinated and dialkoxylated phenylene fragments have been designed and prepared to understand the interactions in fragment orbitals, the influence of the substituents (F, OMe) on the HOMO–LUMO gap, and the role of intramolecular non‐covalent cumulative interactions in the construction of π‐conjugated nanostructures. Their strong conjugation was also

  设计并制备了具有氟化和二烷氧基化亚苯基片段的π共轭亚苯基亚苯基低聚物，以了解片段轨道上的相互作用，取代基（F，OMe）对HOMO-LUMO间隙的影响以及分子内非分子的作用共轭累积相互作用的π共轭纳米结构的建设。紫外光电子能谱和理论计算也证明了它们在气相中的强烈共轭。这些结果可以用二甲氧基亚苯基的π轨道的相对能级位置在确定π/π *中的关键作用来解释。氟化亚苯基实体的轨道水平。二烷氧基亚苯基提高了HOMO轨道，而氟化亚苯基降低了低聚物中的LUMO轨道。此外，氟化亚苯基噻吩化合物中S⋅⋅⋅F和H⋅⋅⋅F相互作用的存在会增加混合目标中S⋅⋅⋅O的相互作用，并有助于低聚物的完全共轭，从而导致弱共价。所涉及的芳族循环之间的环间角。这些结果表明π系统的扩展共轭，这是由狭窄的HOMO-LUMO间隙（根据DFT计算）和相对强的最大波长（由TD-DFT计算和实验性UV / Vis测量获得）所证实的。两种
• Synthesis of novel platinum complex core as a selective Ag⁺ sensor and its H-bonded tetrads self-assembled with triarylamine dendrimers for electron/energy transfers
  作者：Muthaiah Shellaiah、Mandapati V. Ramakrishnam Raju、Ashutosh Singh、Hsin-Chieh Lin、Kung-Hwa Wei、Hong-Cheu Lin

  DOI：10.1039/c4ta04231j

  日期：——

  A novel metal complex PtC was synthesized and utilized in the formation of H-bonded tetrads with two generations of dendrimers (TPAD1 and TPAD2) and as a selective Ag⁺ sensor.

  合成了一种新型金属配合物 PtC，并在与两代树状聚合物（TPAD1和TPAD2）形成氢键四聚体以及作为选择性Ag⁺传感器中使用。
• Synthesis of Soluble Phenyl-Substituted Poly(<i>p</i>-phenylenevinylenes) with a Low Content of Structural Defects
  作者：D. Mikael Johansson、Xiangjun Wang、Tomas Johansson、Olle Inganäs、Gang Yu、Gordana Srdanov、Mats R. Andersson

  DOI：10.1021/ma011768m

  日期：2002.6.1

  The synthesis and characterization of two new soluble poly(p-phenylenevinylenes) (PPVs) are reported. The polymers are poly(2-2',5'-bis(octyloxy)benzene)-1,4-phenylenevinylene) (BOP-PPV) and poly(2-(2',5'-bis(octyloxy)benzene)-5-methoxy-1,4-phenylenevinylene) (BOPM-PPV). Both polymers have been polymerized at high and low temperatures to study the formation of structural defects. It is shown that both methoxy groups as side chains and low polymerization temperatures decrease the content of defects in the final polymer. As a consequence, the polymers with lower concentration of defects exhibit higher electroluminescence yields in light-emitting diodes. In addition to this, the polymers with a low content of defects exhibited longer operational lifetimes in these devices. The highest photoluminescence quantum yield in the solid state and electroluminescence efficiency were found to be 72% and 1.74%, respectively.