N-octyl-2,6-bis(2'-thienyl)dithieno[3,2-b:2',3'-d]pyrrole

• 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: N-octyl-2,6-bis(2'-thienyl)dithieno[3,2-b:2',3'-d]pyrrole
• 英文别名: N-octyl-2,6-bis(2-thienyl)dithieno[3,2-b:2',3'-d]pyrrole；7-Octyl-4,10-dithiophen-2-yl-3,11-dithia-7-azatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene；7-octyl-4,10-dithiophen-2-yl-3,11-dithia-7-azatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene
• 化学式: C₂₄H₂₅NS₄
• 分子量: 455.733
• InChiKey: PPGUGSQBDHACBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-辛基-4H-二噻吩并[3,2-b:2,3-d]吡咯 在 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 43.0h， 生成 N-octyl-2,6-bis(2'-thienyl)dithieno[3,2-b:2',3'-d]pyrrole
  参考文献：
  名称：

  Highly Fluorescent Oligothiophenes through the Incorporation of Central Dithieno[3,2-b:2‘,3‘-d]pyrrole Units

  摘要：

  Dithieno[3,2-b:2',3'-d]pyrrole-based terthiophene (2a-c) and quaterthiophene (3a-c) analogues have been prepared from dithieno[3,2-b:2',3'-d]pyrrole (1) via Stille coupling utilizing a one-pot method. In comparison to the parent oligothiophenes (T-n, where n = 2-4), the resulting dithieno[3,2-b:2',3'-d]pyrrole-based systems exhibit enhanced fluorescence efficiencies in solution (up to 53%). These new oligomeric systems also allow the incorporation of solubilizing side chains without the negative steric interactions that typically reduce backbone planarity.

  DOI：

  10.1021/ol052152a

文献信息

• Solution and solid-state properties of highly fluorescent dithieno[3,2-b:2′,3′-d]pyrrole-based oligothiophenes
  作者：Hong Mo、Karla R. Radke、Katsu Ogawa、Christopher L. Heth、Brett T. Erpelding、Seth C. Rasmussen

  DOI：10.1039/c0cp00970a

  日期：——

  Dithieno[3,2-b:2′,3′-d]pyrrole-based terthiophene and quaterthiophene analogues have been prepared from N-functionalized dithieno[3,2-b:2′,3′-d]pyrroles (DTPs) via Stille coupling. In order to thoroughly study the structure–function property relationships within these DTP-based oligothiophenes, an oligomer series was prepared that allows for the investigation of a number of structural effects including

  Dithieno [3,2- b：2'，3'- d ]吡咯-基于 对噻吩 和 四噻吩N-官能化的二硫杂[3,2- b：2'，3'- d ]吡咯（DTP）通过Stille偶联制备了类似物。为了彻底研究其中的结构-功能特性关系DTP的低聚噻吩，制备了一种低聚物系列，可用于研究许多结构效应，包括链长， 噻吩 功能化，以及 吡咯N功能化。由于吡咯N-官能化允许掺入可溶的侧链而没有通常会降低主链平面性的有害空间相互作用，因此，已经仔细研究了这些侧链的大部分对溶液和固态两种光学性质的影响。这DTP-基于 四噻吩， ñ -叔丁基-2,6-双（2'-噻吩基）噻吩并[3,2- b：2'，3'- d ]吡咯通过X射线晶体学表征，发现在单斜空间群P 2 1 / c中结晶，其中a = 17.489（4）Å，b = 7.8855（16）Å，c = 14.540（3）Å，β = 108.37 （3）°，Z =4。通过
• Molecular tuning in highly fluorescent dithieno[3,2-b:2′,3′-d]pyrrole-based oligomers: effects of N-functionalization and terminal aryl unit
  作者：Sean J. Evenson、Ted M. Pappenfus、M. Carmen Ruiz Delgado、Karla R. Radke-Wohlers、J. T. López Navarrete、Seth C. Rasmussen

  DOI：10.1039/c2cp40161d

  日期：——

  series of eight conjugated oligomers consisting of central dithieno[3,2-b:2′,3′-d]pyrroles (DTPs) end-capped with either thienyl or phenyl groups have been prepared from N-alkyl-, N-aryl-, and N-acyl-dithieno[3,2-b:2′,3′-d]pyrroles via Stille and Suzuki cross-coupling. The DTP-based quaterthiophene, N-phenyl-2,6-bis(2-thienyl)dithieno-[3,2-b:2′,3′-d]pyrrole was characterized via X-ray crystallography and

  由N-烷基-，N-芳基制备了一系列八个共轭低聚物，它们由被噻吩基或苯基封端的中心双噻吩并[3,2- b：2'，3'- d ]吡咯（DTP）组成-和N-酰基-二硫代[3,2- b：2'，3'- d ]吡咯通过Stille和Suzuki交叉偶联。基于DTP四噻吩，Ñ -苯基-2,6-双（2-噻吩基）dithieno-并[3,2- b：2'，3'- d ]吡咯的特征在于通过X射线晶体学和发现正交空间群中结晶Pna2 1与一个= 10.8666（3）埃，b = 22.8858（6），C ^ = 7.4246（2）埃，ž = 4的全部低聚物系列被彻底调查通过进行光物理，电化学和DFT计算，以关联芳基端基和N-官能化对所得光学和电子性质的累积影响。通过这种分子调节，发现可以将HOMO能量调节高达0.32V，并且可以产生具有高达92％的溶液荧光效率的高度荧光的低聚物。
• Highly Fluorescent Oligothiophenes through the Incorporation of Central Dithieno[3,2-<i>b</i>:2‘,3‘-<i>d</i>]pyrrole Units
  作者：Karla R. Radke、Katsu Ogawa、Seth C. Rasmussen

  DOI：10.1021/ol052152a

  日期：2005.11.1

  Dithieno[3,2-b:2',3'-d]pyrrole-based terthiophene (2a-c) and quaterthiophene (3a-c) analogues have been prepared from dithieno[3,2-b:2',3'-d]pyrrole (1) via Stille coupling utilizing a one-pot method. In comparison to the parent oligothiophenes (T-n, where n = 2-4), the resulting dithieno[3,2-b:2',3'-d]pyrrole-based systems exhibit enhanced fluorescence efficiencies in solution (up to 53%). These new oligomeric systems also allow the incorporation of solubilizing side chains without the negative steric interactions that typically reduce backbone planarity.