1-bromo-2,5-dioctadecyloxybenzene | 642476-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-bromo-2,5-dioctadecyloxybenzene
• 英文别名: 2-bromo-1,4-dioctadecoxybenzene
• CAS: 642476-84-4
• 化学式: C₄₂H₇₇BrO₂
• 分子量: 693.976
• InChiKey: CISBIFVAVZWNHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.73
• 重原子数：
  45.0
• 可旋转键数：
  36.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-bromo-2,5-dioctadecyloxybenzene 在 氢氧化钾 、 硫酸 、 溶剂黄146 、 pyridinium chlorochromate 、 sodium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 64.0h， 生成 1-bromo-2,5-dioctadecyloxybenzaldehyde
  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：

  对苯二酚 在 氢氧化钾 、 溴 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 1-bromo-2,5-dioctadecyloxybenzene
  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

文献信息

• Influence of the Conjugation Pattern on the Photophysical Properties of Alkoxy-Substituted PE/PV Hybrid Polymers
  作者：Daniel Ayuk Mbi Egbe、Cornelia Bader、Elisabeth Klemm、Liming Ding、Frank E. Karasz、Ulrich-Walter Grummt、Eckhard Birckner

  DOI：10.1021/ma030339g

  日期：2003.12.1

  Alkoxy-substituted phenylene-ethynylene (PE)/phenylene-vinylene (PV) hybrid polymers of general constitutional structure (-Ar-CdropC-Ar-CHdropCH-)(n) (2), (-Ar-CdropC-Ar-CHdropCH-ArCdropC-)(n) (3), and (-Ar-Cdrop-C-Ar-Cdrop-C-Ar-CHdropCH-Ar-CHdropCH-)(n) (4) have been synthesized and characterized. Comparisons of their photophysical properties in solution as well as in solid state (photoconductivity, absorption, emission, and electroluminescence) with those of their corresponding alkoxy-substituted poly(phenylene-ethynylene) (1) and poly(phenylene-vinylene) (5) have been carried out. Large octadecyloxy groups were selected as side chains in order to reduce the effect of pi-pi stacking interaction on the properties of the polymers in the solid state. This resulted in easy detection of photoconductivity and higher fluorescence quantum yields in solid state. The hybrid conjugation pattern in 4 is more favorable for photoconductivity than that in 2. A red shift of the absorption and emission spectra in solution is observed from 1 over 2b, 3, and 4 to 5. LED devices of ITO/PEDOT/polymer/Ca configuration have been fabricated with all compounds, except 2a. The phenylvinylene side groups in 3 not only give rise to a red shift of the solid-state photoluminescence spectrum and electroluminescence spectrum (relative to 2b) but also bring about a decrease of the turn-on voltage and improve the electroluminescence efficiency for more than 100 times.