2,5-Bis[(S)-2-Methylbutoxy]-4-methylbenzaldehyde | 252684-41-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,5-Bis[(S)-2-Methylbutoxy]-4-methylbenzaldehyde
• CAS: 252684-41-6
• 化学式: C₁₈H₂₈O₃
• 分子量: 292.419
• InChiKey: HGHGGXUMJRDJFZ-KBPBESRZSA-N

物化性质

• 沸点：
  409.0±40.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  21.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,5-Bis[(S)-2-Methylbutoxy]-4-methylbenzaldehyde 在 正丁基锂 、 potassium tert-butylate 作用下， 以 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.08h， 生成 (E,E)-4-{4-(4-Methyl-2,5-bis[(S)-2-methylbutoxy]styryl)-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]-bromobenzene
  参考文献：
  名称：

  Synthesis, Photophysical Properties, and Photovoltaic Devices of Oligo(p-phenylene vinylene)-fullerene Dyads

  摘要：

  The synthesis of a homologous series of oligo(p,-phenylene vinylene)-fulleropyrrolidines (OPVn-C-60, n 1-4, where n is the number of phenyl rings) is described. The photophysical properties of these donor-acceptor dyads and the corresponding model compounds, alpha,omega -dimethyl-2,5-bis(2- (S)-methylbutoxy)-1,4-phenylene vinylene oligomers (OPVn, n = 2-4) and N-methylfulleropyrrolidine (MP-C-60), are studied as a function of the conjugation length in solvents of different polarity and as thin films. Fast singlet energy transfer occurs after photoexcitation of the OPVn moiety of the dyads toward the fullerene moiety in an apolar solvent. Photoexcitation of the dyads in a polar solvent results in electron transfer fur OPV3-C-60 and OPV4-C-60. and to some extent for OPV2-C-60, but not for OPV1-C-60 These results are compared to the results obtained for mixtures of OPVn and MP-C-60 in the same solvents. The solvent-dependent change in free energy for charge separation of the donor-acceptor systems is calculated from the Weller equation, and the rate constants for energy and electron transfer are derived from the fluorescence lifetime and quenching. The results show that in a polar solvent electron transfer in these dyads is likely to occur via a two-step process, that is, a very fast singlet energy transfer prior to charge separation. In thin solid films of OPV3-C-60 and OPV4-C-60, a long-lived charge-separated state is Termed after photoexcitation. The long lifetime in the film is attributed to the migration of charges to different molecules. A flexible photovoltaic device is prepared from OPV4-C-60.

  DOI：

  10.1021/jp001717b
• 作为产物：
  描述：

  (S)-2-甲基丁基对甲苯磺酸酯 在 四丁基氯化铵 、 potassium carbonate 、 三氯氧磷 作用下， 以 氯仿 、 丁酮 为溶剂， 反应 64.0h， 生成 2,5-Bis[(S)-2-Methylbutoxy]-4-methylbenzaldehyde
  参考文献：
  名称：

  Synthesis, Photophysical Properties, and Photovoltaic Devices of Oligo(p-phenylene vinylene)-fullerene Dyads

  摘要：

  The synthesis of a homologous series of oligo(p,-phenylene vinylene)-fulleropyrrolidines (OPVn-C-60, n 1-4, where n is the number of phenyl rings) is described. The photophysical properties of these donor-acceptor dyads and the corresponding model compounds, alpha,omega -dimethyl-2,5-bis(2- (S)-methylbutoxy)-1,4-phenylene vinylene oligomers (OPVn, n = 2-4) and N-methylfulleropyrrolidine (MP-C-60), are studied as a function of the conjugation length in solvents of different polarity and as thin films. Fast singlet energy transfer occurs after photoexcitation of the OPVn moiety of the dyads toward the fullerene moiety in an apolar solvent. Photoexcitation of the dyads in a polar solvent results in electron transfer fur OPV3-C-60 and OPV4-C-60. and to some extent for OPV2-C-60, but not for OPV1-C-60 These results are compared to the results obtained for mixtures of OPVn and MP-C-60 in the same solvents. The solvent-dependent change in free energy for charge separation of the donor-acceptor systems is calculated from the Weller equation, and the rate constants for energy and electron transfer are derived from the fluorescence lifetime and quenching. The results show that in a polar solvent electron transfer in these dyads is likely to occur via a two-step process, that is, a very fast singlet energy transfer prior to charge separation. In thin solid films of OPV3-C-60 and OPV4-C-60, a long-lived charge-separated state is Termed after photoexcitation. The long lifetime in the film is attributed to the migration of charges to different molecules. A flexible photovoltaic device is prepared from OPV4-C-60.

  DOI：

  10.1021/jp001717b

文献信息

• Transfer of π-Conjugated Columnar Stacks from Solution to Surfaces
  作者：Pascal Jonkheijm、Freek J. M. Hoeben、Ralf Kleppinger、Jeroen van Herrikhuyzen、Albertus P. H. J. Schenning、E. W. Meijer

  DOI：10.1021/ja0383118

  日期：2003.12.1

  Three hydrogen-bonded oligo(p-phenylenevinylene)s, OPV3, OPV4, and OPV5, that differ in conjugation length have been synthesized and fully characterized. All three compounds contain chiral side chains, long aliphatic chains, and a ureido-s-triazine hydrogen bonding unit. H-1 NMR and photophysical measurements show that the OPV oligomers grow hierarchically in an apolar solvent; initially, dimers are formed by hydrogen bonds that subsequently develop into stacks by pi-pi interactions of the phenylenevinylene backbone with induced helicity via the chiral side chains. SANS measurements show that rigid cylindrical objects are formed. Stacks of OPV4 have a persistence length of 150 nm and a diameter of 6 nm. OPV3 shows rigid columnar domains of 60 nm with a diameter of 5 nm. Temperature and concentration variable measurements show that the stability of the stacks increases with the conjugation length as a result of more favorable pi-pi interactions. The transfer of the single cylinders from solution to a solid support as isolated objects is only possible when specific concentrations and specific solid supports are used as investigated by AFM. At higher concentrations, an intertwined network is formed, while, at low concentration, ill-defined globular objects are observed. Only in the case of inert substrates (graphite and silicium oxide) single fibers are visible. In the case of the repulsive surfaces (mica and glass), clustering of the stacks occurs, while, at attractive surfaces (gold), the stacks are destroyed.
• Sequential Energy and Electron Transfer in Aggregates of Tetrakis[oligo(<i>p</i>-phenylene vinylene)] Porphyrins and C₆₀ in Water
  作者：Martin Wolffs、Freek J. M. Hoeben、Edwin H. A. Beckers、Albertus P. H. J. Schenning、E. W. Meijer

  DOI：10.1021/ja054406t

  日期：2005.10.1

  Chiral aggregation of oligo(p-phenylene vinylene)-functionalized Zn and free-base porphyrins is observed in water. The formation of mixed assemblies containing both porphyrins results in sequential energy transfer from OPV via zinc porphyrin to free-base porphyrin. Furthermore, the incorporation of C60 as electron acceptor yields a charge separated state by ultimate electron transfer.