2,5-Dioctylbenzene-1,4-dicarbaldehyde | 220980-45-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-Dioctylbenzene-1,4-dicarbaldehyde
• 英文别名: 2,5-dioctylterephthalaldehyde
• CAS: 220980-45-0
• 化学式: C₂₄H₃₈O₂
• 分子量: 358.565
• InChiKey: SEOYKLHHMQHQGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  26
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2,5-Difluoro-benzyl)-phosphonic acid dimethyl ester 、 2,5-Dioctylbenzene-1,4-dicarbaldehyde 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到trans,trans-1,4-bis<2-(2',5'-difluoro)phenylethenyl>-2,5-dioctylbenzene
  参考文献：
  名称：

  Effect of Aromatic Ring Substitution on the Optical Properties, Emission Dynamics, and Solid-State Behavior of Fluorinated Oligophenylenevinylenes

  摘要：

  Several substituted oligopbenylenevinylenes were synthesized using the Wittig-Horner-Emmons reaction to produce the trans isomers. Optical properties of these compounds were evaluated using absorption and steady-state fluorescence spectroscopy. Fluorescence quantum yields, Phi(f), decrease with increasing solvent polarity and approach unity in nonpolar solvents In the case of substituted trans,trans-1,4-bis[2-(2',5'-difluoro)-phenylethenyl]benzenes and trans,trans-1,4-bis[2-(2',5'-dialkoxy)phenylethenyl)-2,3,5,6-tetrafluorobenzenes. The compounds show a strong solvatochromic shift as a function of solvent polarity, yielding a slope of -13 300 cm(-1) according to the Lippert-Mataga equation and indicating the emission of an additional charge-transfer species. A two-state reaction model was confirmed for trans,trans-1,4-bis[2-(2',5'dialkoxy)phenylethenyl)-2,3,5,6-tetratfluorobenzene (6d) in different solvents by time-correlated single-photon counting using global analysis. A dependence of the kinetic data on solvent polarity was found (global fitted decay times in picoseconds for tau(1) and tau(2): 381/1281 in n-hexane; 101/1590 in toluene; 27/2974 in acetonitrile). Investigations of the solid state showed liquid crystalline behavior for 6d and for trans,trans-1,4-bis[2-(2',5'-difluoro)phenylethenyl] 2,5-diheptyloxybenzene (3b). This was confirmed by polarization microscopy and thermal analysis. Both the long alkoxy chains and fluorine substitution are responsible for the formation of mesophases. Photoluminescence studies of 3b and 6d in the solid state indicated an intense emission that was yellow for 3b.

  DOI：

  10.1021/ja983308n
• 作为产物：
  描述：

  1,4-dibromo-2,5-dioctylbenzene 在 正丁基锂 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 水 、 苯 为溶剂， 反应 8.42h， 生成 2,5-Dioctylbenzene-1,4-dicarbaldehyde
  参考文献：
  名称：

  一系列新型PPV半导体类型聚合物的高载流子迁移率

  摘要：

  介绍了一系列聚苯撑乙烯（PPV）型半导体聚合物的合成和表征。这些新的聚合物每隔两个亚苯基环被两个相同长度的烷基取代，所述两个烷基为己基，庚基，辛基，壬基，癸基，十一烷基和十二烷基。聚合物是由相应的二烷基二醛通过在高沸点溶剂混合物中与1,4-双（二乙基膦酰基甲基）苯进行的霍纳-沃兹沃思-埃蒙斯缩合反应合成的。发现纯化的聚合物具有在0.01-0.1 cm 2 V -1 s -1范围内的载流子迁移率PR-TRMC技术测得的载流子寿命约为0.1-5 ms。粉末X射线衍射研究为电荷载流子迁移率和寿命出乎意料的大幅度变化提供了可能的解释，该研究提供了假定的结构模型。最后，通过紫外光电子能谱研究了电子结构，并通过以合适的光正性掩模照射为特征的聚合物薄膜的光降解性能，从而允许随后的掺杂以提供高度各向异性的导电图案。

  DOI：

  10.1021/ma025893p

文献信息

• Ruthenium-Catalyzed Knoevenagel Condensation:  A New Route toward Cyano-Substituted Poly(<i>p</i>-phenylenevinylene)s
  作者：Jian Liao、Qing Wang

  DOI：10.1021/ma049243s

  日期：2004.9.1
• Effect of Aromatic Ring Substitution on the Optical Properties, Emission Dynamics, and Solid-State Behavior of Fluorinated Oligophenylenevinylenes
  作者：Bernd Strehmel、Ananda M. Sarker、John H. Malpert、Veronika Strehmel、Holger Seifert、Douglas C. Neckers

  DOI：10.1021/ja983308n

  日期：1999.2.1

  Several substituted oligopbenylenevinylenes were synthesized using the Wittig-Horner-Emmons reaction to produce the trans isomers. Optical properties of these compounds were evaluated using absorption and steady-state fluorescence spectroscopy. Fluorescence quantum yields, Phi(f), decrease with increasing solvent polarity and approach unity in nonpolar solvents In the case of substituted trans,trans-1,4-bis[2-(2',5'-difluoro)-phenylethenyl]benzenes and trans,trans-1,4-bis[2-(2',5'-dialkoxy)phenylethenyl)-2,3,5,6-tetrafluorobenzenes. The compounds show a strong solvatochromic shift as a function of solvent polarity, yielding a slope of -13 300 cm(-1) according to the Lippert-Mataga equation and indicating the emission of an additional charge-transfer species. A two-state reaction model was confirmed for trans,trans-1,4-bis[2-(2',5'dialkoxy)phenylethenyl)-2,3,5,6-tetratfluorobenzene (6d) in different solvents by time-correlated single-photon counting using global analysis. A dependence of the kinetic data on solvent polarity was found (global fitted decay times in picoseconds for tau(1) and tau(2): 381/1281 in n-hexane; 101/1590 in toluene; 27/2974 in acetonitrile). Investigations of the solid state showed liquid crystalline behavior for 6d and for trans,trans-1,4-bis[2-(2',5'-difluoro)phenylethenyl] 2,5-diheptyloxybenzene (3b). This was confirmed by polarization microscopy and thermal analysis. Both the long alkoxy chains and fluorine substitution are responsible for the formation of mesophases. Photoluminescence studies of 3b and 6d in the solid state indicated an intense emission that was yellow for 3b.
• [EN] ELECTRONICALLY CONDUCTIVE PPV COPOLYMERS<br/>[FR] COPOLYMERES DE POLYPHENYLENE VINYLES (PPV) ALTERNES ELECTRONIQUEMENT CONDUCTEURS
  申请人：RISOE NAT LAB

  公开号：WO2003078498A1

  公开（公告）日：2003-09-25

  A polymer material having repeating units of the structure shown in general Formula (3) in which each R independently is alkyl (e.g. linear C8 alkyl), and n is a number of at least 20, indicating the average degree of polymerisation, has conductive properties is useful in photovoltaic devices and may be produced by reacting a e.g. 1,4-diformyl-2,5-dialkylbenzene with e.g. p-xylene-bis-phosponicacidtetraethylester in a high boiling solvent under basic conditions.
• High Carrier Mobility in a Series of New Semiconducting PPV-Type Polymers
  作者：Frederik C. Krebs、Mikkel Jørgensen

  DOI：10.1021/ma025893p

  日期：2003.6.1

  The synthesis and characterization of a series of semiconducting polymers of the polyphenylenevinylene (PPV) type is presented. These new polymers have every second phenylene ring substituted by two alkyl groups of equal length which are hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl. The polymers were synthesized from the corresponding dialkyldialdehydes by a Horner−Wadsworth−Emmons condensation

  介绍了一系列聚苯撑乙烯（PPV）型半导体聚合物的合成和表征。这些新的聚合物每隔两个亚苯基环被两个相同长度的烷基取代，所述两个烷基为己基，庚基，辛基，壬基，癸基，十一烷基和十二烷基。聚合物是由相应的二烷基二醛通过在高沸点溶剂混合物中与1,4-双（二乙基膦酰基甲基）苯进行的霍纳-沃兹沃思-埃蒙斯缩合反应合成的。发现纯化的聚合物具有在0.01-0.1 cm 2 V -1 s -1范围内的载流子迁移率PR-TRMC技术测得的载流子寿命约为0.1-5 ms。粉末X射线衍射研究为电荷载流子迁移率和寿命出乎意料的大幅度变化提供了可能的解释，该研究提供了假定的结构模型。最后，通过紫外光电子能谱研究了电子结构，并通过以合适的光正性掩模照射为特征的聚合物薄膜的光降解性能，从而允许随后的掺杂以提供高度各向异性的导电图案。