(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 | 312702-80-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (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
• CAS: 312702-80-0
• 化学式: C₅₃H₇₉BrO₆
• 分子量: 892.111
• InChiKey: RXXDTUMYICPFKA-HNQUAAOBSA-N

物化性质

• 沸点：
  852.4±65.0 °C(predicted)
• 密度：
  1.073±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.65
• 重原子数：
  60.0
• 可旋转键数：
  28.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (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 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.58h， 生成 (E,E,E)-4-[4-{4-(4-Methyl-2,5-bis[(S)-2-methylbutoxy]styryl)-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]styryl]-2,5-bis[(S)-2-methylbutoxy]benzaldehyde
  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 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 偶氮二异丁腈 、 potassium tert-butylate 、 四丁基氯化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 36.58h， 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

文献信息

• Energy Transfer in Supramolecular Assemblies of Oligo(<i>p</i>-phenylene vinylene)s Terminated Poly(propylene imine) Dendrimers
  作者：Albertus P. H. J. Schenning、Emiel Peeters、E. W. Meijer

  DOI：10.1021/ja000099+

  日期：2000.5.1

  Poly(propylene imine) dendrimers have been functionalized with π-conjugated oligo(p-phenylene vinylene)s (OPV's) through an amide linkage and are fully characterized. In solution the dendrimers behave as globular entities without specific interactions between the OPV units. The OPV dendrimers have an amphiphilic nature and self-assemble at the air−water interface forming stable monolayers in which

  聚（丙烯亚胺）树枝状聚合物已通过酰胺键用 π 共轭低聚（对亚苯基亚乙烯基）（OPV's）进行功能化并得到充分表征。在溶液中，树枝状聚合物表现为球状实体，OPV 单元之间没有特定的相互作用。OPV 树枝状聚合物具有两亲性，在气水界面自组装形成稳定的单层，其中树枝状表面活性剂可能呈圆柱形；所有 OPV 都垂直于水面排列，树枝状聚（丙烯亚胺）核面向水相。从 Langmuir-Blodgett 薄膜中获取的光谱显示出一个小的蓝移，表明 OPV 单元之间的相互作用。旋涂均匀薄膜可以从含有载有染料的树枝状聚合物的溶液中获得。这些薄膜的光学特性类似于朗缪尔-布洛杰特薄膜，这表明 OPV 的组织类型相同。OPV 树枝状聚合物是...的有效提取剂
• Supramolecular Control over Donor−Acceptor Photoinduced Charge Separation
  作者：Alicia Marcos Ramos、Stefan C. J. Meskers、Edwin H. A. Beckers、Ryan B. Prince、Luc Brunsveld、René A. J. Janssen

  DOI：10.1021/ja0390909

  日期：2004.8.1

  OPV(*)(+)-FOLD-PERY(*)(-) charge-separated state upon photoexcitation. As a result, the extent of photoinduced charge separation depends on the degree of folding of the bridge between donor and acceptor and therefore on the apolar nature of the medium. As a consequence, and contrary to conventional photoinduced charge separation processes, the formation of the OPV(*)(+)-FOLD-PERY(*)(-) charge-separated state is

  通过共价连接对亚苯基亚乙烯基低聚物 (OPV) 和苝二酰亚胺 (PERY) 的十二个苯环间亚苯基亚乙炔低聚物 (FOLD) 的两端，合成了一种新型供体-桥-受体系统，其中含有非极性(S)-3,7-二甲基-1-辛氧基侧链。为了比较，已经制备了其中不存在供体或受体的模型化合物。在氯仿中，寡聚桥呈无规卷曲构象。添加非极性溶剂（庚烷）后，低聚桥首先折叠成螺旋状堆叠，随后发生堆叠的分子间自组装成柱状结构。无规卷曲构象中的光激发，其中供体和受体发色团之间的相互作用很小，仅导致长程分子内能量转移，其中 OPV 单线态激发态转变为 PERY 单线态激发态。在桥的折叠构象中，供体和受体更接近，它们增强的相互作用有利于在光激发时形成 OPV(*)(+)-FOLD-PERY(*)(-) 电荷分离状态。因此，光致电荷分离的程度取决于供体和受体之间桥的折叠程度，因此取决于介质的非极性。因此，与传统的光致电荷分离过程相反，在非极性介质中更倾向于形成