1,4-bis(octyloxy)benzene-2-boronic acid | 442911-57-1

• 英文名称: 1,4-bis(octyloxy)benzene-2-boronic acid
• 英文别名: 2,5-dioctyloxybenzeneboronic acid；2,5-dioctyloxyphenylboronic acid；(2,5-Dioctoxyphenyl)boronic acid
• CAS: 442911-57-1
• 化学式: C₂₂H₃₉BO₄
• 分子量: 378.36
• InChiKey: RQRKGNQMDBNBRV-UHFFFAOYSA-N

物化性质

• 沸点：
  527.7±60.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  27
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-bis(octyloxy)benzene-2-boronic acid 在 四(三苯基膦)钯 lithium aluminium tetrahydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 1.0h， 生成 2-(2',5'-bis(octyloxy)benzene)-1,4-bis(hydroxymethyl)-benzene
  参考文献：
  名称：

  Synthesis of Soluble Phenyl-Substituted Poly(p-phenylenevinylenes) with a Low Content of Structural Defects

  摘要：

  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.

  DOI：

  10.1021/ma011768m
• 作为产物：
  描述：

  1,2-(二辛氧荃)苯 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 1,4-bis(octyloxy)benzene-2-boronic acid
  参考文献：
  名称：

  Synthesis of Soluble Phenyl-Substituted Poly(p-phenylenevinylenes) with a Low Content of Structural Defects

  摘要：

  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.

  DOI：

  10.1021/ma011768m

文献信息

• Electroactive Nanorods and Nanorings Designed by Supramolecular Association of π-Conjugated Oligomers
  作者：Olivier J. Dautel、Mike Robitzer、Jean-Charles Flores、Denis Tondelier、Françoise Serein-Spirau、Jean-Pierre Lère-Porte、David Guérin、Stéphane Lenfant、Monique Tillard、Dominique Vuillaume、Joël J. E. Moreau

  DOI：10.1002/chem.200701638

  日期：2008.5.9

  techniques (AFM, EFM, etc.). Nano-objects have successfully been fabricated from the pristine organogel under appropriate dilution conditions. In particular, nanorods and nanorings composed of the electroactive organogelator have been isolated and characterized. With additional support from an electrochemical study of the organogelator in solution, it has been demonstrated by the EFM technique that such nano-objects

  在对半导体纳米物体的设计和隔离的研究中，已经实现了新的双脲基π-π共轭有机胶凝剂的合成。发现该低聚（亚苯基亚乙撑基）衍生物能够形成一维超分子组装体，从而导致几种溶剂的凝胶化。已经用不同的技术（AFM，EFM等）研究了它的自组装特性。纳米物体已经在适当的稀释条件下成功地由原始有机凝胶制成。特别地，已经分离和表征了由电活性有机胶凝剂组成的纳米棒和纳米环。在溶液中有机胶凝剂的电化学研究的额外支持下，通过EFM技术已经证明，这种纳米物体能够展现电荷传输特性，这是制造纳米级光电器件所必需的。观察到可以在微米上沿单个纳米物体（纳米节和纳米环）注入正电荷并使其离域，并且值得注意的是，没有电荷存储在纳米环的中心。还观察到纳米结构中的地形构造阻止了运输和离域。在负偏压下（即电子注入）进行了相同的实验，但未观察到电荷离域。这些结果可能与1的性质有关，后者是一个良好的电子给体，因此它很容易被氧化，但很难还原。纳
• 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。
• Stereoselective Synthesis of <i>cis</i>- and <i>trans</i>-Oligo(phenylenevinylene)s via Palladium-Catalyzed Cross-Coupling Reactions
  作者：Hiroyuki Katayama、Masato Nagao、Fumiyuki Ozawa、Masashi Ikegami、Tatsuo Arai

  DOI：10.1021/jo052602c

  日期：2006.3.31

  cis-Oligo(phenylenevinylene)s (OPVs) are synthesized by Suzuki−Miyaura coupling of arylboronic acids with (Z)-bromoalkenes in over 96% geometrical purity. On the other hand, trans-oligo(phenylenevinylene)s can be synthesized by Hiyama coupling of aryl iodide with (E)-alkenylsilanes in almost perfect purities. Effect of π-conjugation chain length on photoisomerization behavior of OPVs is described.

  顺式-低聚（亚苯基亚乙烯基）（OPV）是通过芳族硼酸与（Z）-溴代烯烃的Suzuki-Miyaura偶联以96％以上的几何纯度合成的。另一方面，反式-低聚（亚苯基亚乙烯基）可以通过芳基碘化物与（E）-烯基硅烷的Hiyama偶联以几乎完美的纯度来合成。描述了π共轭链长度对OPVs光异构化行为的影响。
• Stereocontrolled Synthesis and Optical Properties of All-cis Poly(phenylene vinylenes) (PPVs):  A Method for Direct Patterning of PPVs
  作者：Hiroyuki Katayama、Masato Nagao、Tatsuro Nishimura、Yukio Matsui、Kazutoshi Umeda、Kensuke Akamatsu、Takaaki Tsuruoka、Hidemi Nawafune、Fumiyuki Ozawa

  DOI：10.1021/ja042853n

  日期：2005.3.1

  Geometrically pure, all-cis poly(phenylene vinylenes) (PPVs) are synthesized by Suzuki-Miyaura-type polycondensation of 2,5-dioctyloxy-1,4-benzenediboronic acid with (Z, Z)-bis(2-bromoethenyl)benzenes, which are prepared by ruthenium-catalyzed (Z)-selective double hydrosilylation of diethynylbenzenes, followed by bromodesilylation of the resulting (Z, Z)-bis(2-silylethenyl)benzenes with N-bromosuccinimide. The all-cis PPVs thus obtained undergo one-way photoisomerization to the corresponding trans-PPVs both in solution and in the solid. This phenomenon is applied to direct microscale patterning of PPVs onto a quartz substrate.