5''''-Bromo-4''-octyl-[2,2';5',2'';5'',2''';5''',2'''']quinquethiophene-5-carboxylic acid benzyl ester | 288860-95-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5''''-Bromo-4''-octyl-[2,2';5',2'';5'',2''';5''',2'''']quinquethiophene-5-carboxylic acid benzyl ester
• 英文别名: Benzyl 5-[5-[5-[5-(5-bromothiophen-2-yl)thiophen-2-yl]-4-octylthiophen-2-yl]thiophen-2-yl]thiophene-2-carboxylate
• CAS: 288860-95-7
• 化学式: C₃₆H₃₃BrO₂S₅
• 分子量: 737.891
• InChiKey: NDIPBJSHIHWGMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  168
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5''''-Bromo-4''-octyl-[2,2';5',2'';5'',2''';5''',2'''']quinquethiophene-5-carboxylic acid benzyl ester 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 89.0h， 生成 5'''''''-Bromo-4'',4'''''-dioctyl-[2,2';5',2'';5'',2''';5''',2'''';5'''',2''''';5''''',2'''''';5'''''',2''''''']octithiophene-5-carboxylic acid benzyl ester
  参考文献：
  名称：

  Well-Defined Triblock Hybrid Dendrimers Based on Lengthy Oligothiophene Cores and Poly(benzyl ether) Dendrons

  摘要：

  DOI：

  10.1021/ja9818147
• 作为产物：
  描述：

  2,2'-联二噻吩 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 5''''-Bromo-4''-octyl-[2,2';5',2'';5'',2''';5''',2'''']quinquethiophene-5-carboxylic acid benzyl ester
  参考文献：
  名称：

  Well-Defined Triblock Hybrid Dendrimers Based on Lengthy Oligothiophene Cores and Poly(benzyl ether) Dendrons

  摘要：

  DOI：

  10.1021/ja9818147

文献信息

• Redox States of Well-Defined π-Conjugated Oligothiophenes Functionalized with Poly(benzyl ether) Dendrons
  作者：Joke J. Apperloo、René A. J. Janssen、Patrick R. L. Malenfant、Lambertus Groenendaal、Jean M. J. Fréchet

  DOI：10.1021/ja994259x

  日期：2000.7.26

  oligothiophene conjugation length varying between 4 and 17 repeat units. The attachment of poly(benzyl ether) dendritic wedges at the termini of these lengthy oligothiophenes considerably enhances their solubility, thus enabling the first detailed investigation of the electronic structure of oligothiophenes having 11 and 17 repeat units with minimal β-substitution. In the case of the undecamer and heptadecamer

  已经使用循环伏安法和变温紫外/可见光/近红外光谱研究了一系列基于低聚噻吩核和聚（苄基醚）树枝状结构的明确混合树枝状聚合物的氧化还原状态。这些新型杂化材料的中性、单氧化和双氧化态的氧化电位和电子跃迁已被确定为 4 到 17 个重复单元之间变化的低聚噻吩共轭长度的函数。在这些长的低聚噻吩的末端连接聚（苄基醚）树枝状楔形物大大提高了它们的溶解度，从而能够对具有 11 和 17 个重复单元的低聚噻吩的电子结构进行第一次详细研究，并具有最小的 β-取代。在十一聚体和七聚体的情况下，我们发现双极化状态由两个单独的极化子组成，而不是一个双极化子。树枝状聚（苄基醚）增溶剂对氧化还原性能的影响...
• Controlling Solubility and Modulating Peripheral Function in Dendrimer Encapsulated Dyes
  作者：Paul Furuta、Jean M. J. Fréchet

  DOI：10.1021/ja037133f

  日期：2003.10.1

  The synthesis of large dendrons and dendrimers with site-isolated dyes at their core has been explored. The dyes selected for this work were coumarin 343 and pentathiophene, as energy transfer processes prevail when the two dyes are intimately mixed but each should behave independently of the other if site-isolation is achieved. Because the two dyes have very different functional characteristics, a protocol involving orthogonal protecting groups and allowing the use of a single family of electroactive dendrons for their encapsulation had to be developed. The synthetic protocol must balance the need to incorporate electroactive groups at the periphery of the dendrons with the requirement for high solubility and a size sufficient to fully encapsulate the central dye. Because of their poor solubility and tendency to crystallize, dendrons with uniform triarylamine substitution proved unsatisfactory leading to the development of new unsymmetrical dendrons with alternating branched alkyl groups and triarylamine moieties at their periphery. These dendrons, which show excellent solubility and no tendency to crystallize, were assembled into large dendrimers using a modular protocol with the light emitting dye at their core. It is expected that the large size of the dendritic shell will provide effective site-isolation for the encapsulated central dyes enabling them to exhibit their intrinsic emission properties with minimal energy transfer between neighboring core fluorophores when processed in bulk thin films.