4-bromo-2,5-dioctyloxybenzaldehyde | 431898-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-bromo-2,5-dioctyloxybenzaldehyde
• 英文别名: 4-bromo-2,5-bis(octyloxy)benzaldehyde；1-bromo-4-formyl-2,5-dioctyloxybenzene；4-Bromo-2,5-bis(octyloxy)benzaldehyde；4-bromo-2,5-dioctoxybenzaldehyde
• CAS: 431898-09-8
• 化学式: C₂₃H₃₇BrO₃
• 分子量: 441.449
• InChiKey: GZBWYDQXDTUPJS-UHFFFAOYSA-N

物化性质

• 沸点：
  512.5±50.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  27
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromo-2,5-dioctyloxybenzaldehyde 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 氢氧化钾 、 copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 33.0h， 生成 1,4-bis(4-formyl-2,5-dioctyloxyphenyl)butadiyne-1,3
  参考文献：
  名称：

  Investigation of the Photophysical and Electrochemical Properties of Alkoxy-Substituted Arylene−Ethynylene/Arylene−Vinylene Hybrid Polymers

  摘要：

  High-molecular-weight, soluble and thermostable alkoxy-substituted arylene-ethynylene/ arylene-vinylene conjugated polymers, 13 and 14, have been successfully synthesized through the Horner-Wadsworth-Emmons olefination of luminophoric dialdehydes 7 and 9 and bisphosphonate 12 in very good yields. They were characterized through H-1 NMR, C-13 NMR, IR, and elemental analysis. The investigation of their photophysical and electrochemical properties has been carried out. Although almost identical absorption and emission spectra were obtained in dilute chloroform solution for all polymers 13, the full width at half-maximum (fwhm) value of the emission curves depends on the length of the attached side chains. The presence of anthracenylene units in 14 leads to a red shift of its absorption and emission spectra relative to 13. Strong self-reabsorption after excitation in solution was observed for this polymer. The solid-state photophysical properties of 13 and 14 (photoconductivity, absorption and emission spectra, fluorescence quantum yield, Stokes shift, and fwhm) greatly depend on the nature (linear or branched), length, and location of the grafted alkoxy side groups. Photoconductivity is easily detected in polymers having octadecyloxy chains (13aa, 13ab, 14). Long linear (octadecyl, i.e., 13aa) or short branched (2-ethylhexyl, i.e., 13cc) side chains at position R-2 (phenylene-vinylene segment) are necessary to obtain sharp and well-resolved emission spectra accompanied by high fluorescence quantum yields. The quasi-donor (phenylene-vinylene segment)-acceptor (arylene-ethynylene segment) nature of these polymers could explain the great discrepancy between the electrochemical band gap energy, E-g(ec) approximate to 1.60 eV, as obtained from the onset values of the redox potentials in cyclic voltammetry and in differential pulse polarography measurements, and the optical band gap energy, E-g(opt) approximate to 2.30 eV, from the absorption spectra.

  DOI：

  10.1021/ma0301395
• 作为产物：
  描述：

  溴羟基喹啉 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 、 二甲基亚砜 为溶剂， 反应 44.5h， 生成 4-bromo-2,5-dioctyloxybenzaldehyde
  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

• Synthesis of Rigid<i>π</i>-Conjugated Mono-, Bis-, Tris-, and Tetrakis(terpyridine)s: Influence of the Degree and Pattern of Substitution on the Photophysical Properties
  作者：Andreas Winter、Christian Friebe、Martin D. Hager、Ulrich S. Schubert

  DOI：10.1002/ejoc.200800857

  日期：2009.2

  series of rigid π-conjugated mono-, bis-, tris-, and tetrakis(terpyridine)s 3–8 was synthesized in high yields by means of Horner–Wadsworth–Emmons (HWE) reactions between benzyl phosphonates 1 and an aldehyde-functionalized terpyridine derivative 2. The photophysical properties of the materials in solution and in the solid state depend strongly both on the numbers of terpyridine moieties attached to the

  通过苄基膦酸酯 1 和醛-的 Horner-Wadsworth-Emmons (HWE) 反应，以高产率合成了一系列刚性 π 共轭单-、双-、三-和四（三联吡啶）3-8。功能化的三联吡啶衍生物 2. 溶液和固态材料的光物理性质在很大程度上取决于连接到中心苯基核的三联吡啶部分的数量和化合物的几何形状。邻位取代化合物 5 和 8 的光物理行为表明几何形状发生了显着变化，同时激发后有效 π 共轭系统的主要扩展。对于四（三联吡啶）衍生物 8，观察到具有高量子产率的亮绿色发射。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Tunable Optical Properties of Chromophores Derived from Oligo(<i>p</i>-phenylene vinylene)
  作者：Audrey Guerlin、Frédéric Dumur、Eddy Dumas、Fabien Miomandre、Guillaume Wantz、Cédric R. Mayer

  DOI：10.1021/ol1007263

  日期：2010.5.21

  A series of 11 symmetric push−pull chromophores consisting of electron-accepting groups connected through a central π-conjugated system derived from oligo(p-phenylene vinylene) (OPV) were designed and synthesized. Electronic and spectroscopic properties were investigated by UV−visible absorption, fluorescence spectroscopy, and cyclic voltammetry. By finely tuning the electron-withdrawing ability of

  设计并合成了11个对称的推挽发色团，这些发色团由通过寡聚（对苯亚乙烯基）（OPV）衍生的中心π共轭体系连接的电子接受基组成。通过紫外可见吸收，荧光光谱和循环伏安法研究了电子和光谱性质。通过微调受体的吸电子能力以及π共轭间隔基的长度，获得了表现出强吸收和发射的多种染料。
• 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。
• PHOSPHORESCENT ORGANIC COMPOUNDS
  申请人：Kim Jinsang

  公开号：US20120248337A1

  公开（公告）日：2012-10-04

  Compositions providing metal-independent phosphorescence due to a directed heavy atom effect are provided. Methods of providing a phosphorescent composition are also provided where a directed heavy atom effect is maintained to cause the composition to be phosphorescent. Manufacture of phosphorescent compositions using intermolecular and intramolecular directed heavy atom effects are disclosed.

  本发明提供了由定向重原子效应引起的独立于金属的磷光性的组合物。还提供了提供磷光性组合物的方法，其中维持定向重原子效应以使组合物呈现磷光性。揭示了使用分子间和分子内定向重原子效应制造磷光性组合物的制造方法。
• Side Chain Effects in Hybrid PPV/PPE Polymers
  作者：Daniel Ayuk Mbi Egbe、Carsten Peter Roll、Eckhard Birckner、Ulrich-Walter Grummt、Regina Stockmann、Elisabeth Klemm

  DOI：10.1021/ma012195g

  日期：2002.5.1

  long linear alkoxy, e.g., dodecyloxy, octadecyloxy, or branched alkoxy side chains, e.g., 2-ethylhexyloxy, on the conjugated backbone. Thermotropic and lyotropic liquid crystalline behavior was observed with polarized optical microscopy. The presence of triple bonds along the PPV backbone increases the electron affinity of these polymers, which is reflected by the comparatively (with MEH−PPV) higher

  发光体二醛1和2与双膦酸酯3的霍纳-沃兹沃思-埃蒙斯烯化反应可提供具有明确定义的一般结构的高分子量且热稳定的PPV / PPE杂化聚合物4和5-（CH CH-Ph-CH CH- Ph-C⋮C-Ph-C⋮C-Ph-）n，已通过NMR，红外和元素分析证实。将长链状烷氧基（例如十二烷氧基，十八烷氧基）或支链烷氧基侧链（例如2-乙基己氧基）连接到共轭主链上后，即可获得可溶性且良好的成膜材料。用偏光光学显微镜观察了热致和溶致液晶行为。沿着PPV主链的三键的存在增加了这些聚合物的电子亲和力，这相对于（使用MEH-PPV）相对于Ag / AgCl较高的1.30 V氧化电势反映出来。聚合物4和5是良好的光电导和高发光材料。虽然所有4型聚合物的光物理行为几乎相同（λmax，abs在稀氯仿溶液中获得450 nm，λmax，em = 490 nm）或5（λmax，abs = 470 nm，λmax，em = 553