4,5-bis(2'-ethylhexyloxy)-1,2-dibromobenzene | 157789-12-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,5-bis(2'-ethylhexyloxy)-1,2-dibromobenzene
• 英文别名: 1,2-dibromo-4,5-di(2'-ethylhexyloxy)benzene；1,2-dibromo-4,5-bis(2-ethylhexyloxy)benzene；1,2-Dibromo-4,5-bis[(2-ethylhexyl)oxy]benzene；1,2-dibromo-4,5-bis(2-ethylhexoxy)benzene
• CAS: 157789-12-3
• 化学式: C₂₂H₃₆Br₂O₂
• 分子量: 492.335
• InChiKey: CXUXBXXIAIQJGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  26
• 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：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-bis(2'-ethylhexyloxy)-1,2-dibromobenzene 在 iron(III) chloride 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 硝基甲烷 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 5,6-bis((2-ethylhexyl)oxy)naphtho[2,1-b:3,4-b']dithiophene
  参考文献：
  名称：

  Naphthodithiophene-2,1,3-benzothiadiazole copolymers for bulk heterojunction solar cells

  摘要：

  两种新合成的萘二噻吩类共聚物PNB，具有约1.64 eV的低光学带隙，使用PNB和PC71BM混合物制成的太阳能电池获得了5.3%的功率转换效率，并在广泛的频谱范围内实现了超过60%的外部量子效率。

  DOI：

  10.1039/c1cc13690a
• 作为产物：
  描述：

  溴代异辛烷 在 N-溴代丁二酰亚胺(NBS) 、 potassium hydroxide 作用下， 以 乙醇 、 氯仿 、 溶剂黄146 为溶剂， 反应 10.0h， 生成 4,5-bis(2'-ethylhexyloxy)-1,2-dibromobenzene
  参考文献：
  名称：

  Naphthodithiophene-2,1,3-benzothiadiazole copolymers for bulk heterojunction solar cells

  摘要：

  两种新合成的萘二噻吩类共聚物PNB，具有约1.64 eV的低光学带隙，使用PNB和PC71BM混合物制成的太阳能电池获得了5.3%的功率转换效率，并在广泛的频谱范围内实现了超过60%的外部量子效率。

  DOI：

  10.1039/c1cc13690a

文献信息

• Naphtho[2,1-b:3,4-b′]bisthieno[3,2-b][1]benzothiophene-based semiconductors for organic field-effect transistors
  作者：Zhaoguang Li、Ji Zhang、Kai Zhang、Weifeng Zhang、Lei Guo、Jianyao Huang、Gui Yu、Man Shing Wong

  DOI：10.1039/c5tc00631g

  日期：——

  Naphtho[2,1-b:3,4-b′]bisthieno[3,2-b][1]benzothiophene derivatives exhibiting a hole mobility of up to 0.25 cm² V⁻¹ s⁻¹ show promise as useful building blocks to construct next-generation high performance organic semiconductors.

  Naphtho[2,1-b:3,4-b′]bisthieno[3,2-b][1]benzothiophene衍生物表现出高达0.25 cm^2 V^-1 s^-1的空穴迁移率，显示出作为构建下一代高性能有机半导体的有用组成部分的潜力。
• Reactive Conducting Thiepin Polymers
  作者：Changsik Song、Timothy M. Swager

  DOI：10.1021/jo902079j

  日期：2010.2.19

  and synthesis of annulated thiepins designed to undergo bent-to-planar transformation driven by aromatization under electrochemical control. Thiepins are conjugated seven-membered ring systems with a thioether in the macrocycle. We synthesized thermally stable thiepins that are electropolymerizable to give rise to thiepin-containing electroactive polymers. Extended thiepin systems undergo sulfur extrusion

  我们报告了设计和合成的环噻吩类化合物的设计和合成，这些化合物经过电化学控制下的芳构化作用，经历了弯曲到平面的转变。噻吩类化合物是在大环中与硫醚共轭的七元环系统。我们合成了可电聚合的热稳定的噻吩，以生成含噻吩的电活性聚合物。扩展的噻吩系统会经受硫磺氧化挤压，并且此功能可用于过氧化物检测。
• New Phenyl-Substituted PPV Derivatives for Polymer Light-emitting Diodes−Synthesis, Characterization and Structure−Property Relationship Study
  作者：Zhi-Kuan Chen、Nancy Hoi Sim Lee、Wei Huang、Yi-She Xu、Yong Cao

  DOI：10.1021/ma021221n

  日期：2003.2.1

  Three new PPV derivatives with dialkoxyphenyl substituents, BEH2P-PPV, BEH3P-PPV, and BEH4P-PPV have been synthesized. The polymers were characterized by FT-IR, H-1 NMR, and elemental analysis. The polymers possess excellent solubility, high molecular weights, high photoluminescence efficiencies and good thermal stability. The influence of substitution pattern on the formation of structural defects has been investigated by measuring the signal due to tolane-bisbenzyl moieties (TBB) in the proton NMR spectra. BEH2P-PPV with a steric phenyl group at the ortho-position on the side phenyl ring shows the lowest amount of TBB, which indicates suitable steric hindrance can be applied to suppress the formation of irregular head-to-head and tail-to-tail linkage in the polymer chains. In addition, the polarity of solvents used for the Gilch polymerization will also affect the amount of irregular structure in the polymers. Polar solvents such as THF will result in polymers with low TBB content. Energy level measurement from cyclic voltammetry revealed that the influences of the substitution pattern on the HOMOs and LUMOs are different. The three polymers possess similar HOMO energy levels while the LUMO of BEH4P-PPV is much higher than that of the other two polymers. Polymer light-emitting diodes fabricated from BEH2P-PPV, BEH3P-PPV, and BEH4P-PPV with the configuration of ITO/PEDOT/polymer/Ba/Al, emitted bright blue-green to green light with the maximum peaks at 496, 488, and 525 nm, respectively. The turn-on electric field and maximum external quantum efficiencies of the diodes are 0.30, 0.50, and 0.42 MV/cm and 0.37%, 0.66%, and 0.25% respectively. The quantum efficiency is mainly determined by the electron injection from the cathode. With the highest luminance, lowest turn-on electric field, and good quantum efficiency as well as negligible structural defects, BEH2P-PPV is the most promising material among the three polymers for polymer light-emitting diodes.
• Naphthodithiophene-2,1,3-benzothiadiazole copolymers for bulk heterojunction solar cells
  作者：Bao Wang、Sai-Wing Tsang、Weifeng Zhang、Ye Tao、Man Shing Wong

  DOI：10.1039/c1cc13690a

  日期：——

  Two newly synthesized naphthodithiophene-based copolymers, PNB, exhibit a low optical bandgap of ∼1.64 eV with which the solar cells fabricated from the blend of PNB and PC71BM afforded a power conversion efficiency of 5.3% with external quantum efficiency over 60% in a broad spectral range.

  两种新合成的萘二噻吩类共聚物PNB，具有约1.64 eV的低光学带隙，使用PNB和PC71BM混合物制成的太阳能电池获得了5.3%的功率转换效率，并在广泛的频谱范围内实现了超过60%的外部量子效率。