2,6-dibromo-N-dodecyldithieno[3,2-b:2',3'-d]pyrrole | 1346137-62-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡咯类
• 英文名称: 2,6-dibromo-N-dodecyldithieno[3,2-b:2',3'-d]pyrrole
• 英文别名: 2,6-Dibromo-4-dodecyl-4H-dithieno[3,2-b:2',3'-d]pyrrole；4,10-dibromo-7-dodecyl-3,11-dithia-7-azatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene
• CAS: 1346137-62-9
• 化学式: C₂₀H₂₇Br₂NS₂
• 分子量: 505.381
• InChiKey: NFGGEWFSEBXMOX-UHFFFAOYSA-N

物化性质

• 沸点：
  548.6±50.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2,2':6',2''-terpyridine 、 2,6-dibromo-N-dodecyldithieno[3,2-b:2',3'-d]pyrrole 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 36.0h， 以75.6%的产率得到2,6-bis(p-(2,2':6',2''-terpyridine-4'-yl)phenyl)-N-dodecyldithieno[3,2-b:2',3'-d]pyrrole
  参考文献：
  名称：

  Terpyridine-based donor–acceptor metallo-supramolecular polymers with tunable band gaps: Synthesis and characterization

  摘要：

  Three new building blocks containing the electron-donor fused-ring motifs carbazole, dithienosilole (DTS) and dithienopyrrole (DTP) and the 2,2':6',2 ''-terpyridine electron-acceptor motif were designed and synthesized. Directed by transition metal ions, the self-assembly of the building blocks triggered polymerization to form the corresponding metallo-supramolecular polymers PCzTPY, PSiTPY and PNTPY, respectively. The UV-vis absorption maxima of the building blocks occur at long wavelengths (351, 368 and 430 nm for CzTPY, SiTPY and NTPY, respectively), which arises from intramolecular charge transfer (ICT) transitions. However, the absorption maxima of their corresponding metallosupramolecular polymers are clearly red-shifted (to 394, 431 and 509 nm for PCzTPY, PSiTPY and PNTPY, respectively), which is caused by the incorporation of the transition metal ion into the backbones of the target polymers. Based on the above strategies, the resulting metallo-polymers exhibit reduced energy gaps, which are 2.07,1.97 and 1.56 eV for the PCzTPY, PSiTPY and PNTPY metallo-supramolecular polymers, respectively. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2016.04.031
• 作为产物：
  描述：

  2,2'-联二噻吩 在 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 水 、 溴 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 溶剂黄146 、 sodium t-butanolate 、 锌 作用下， 以 丙醇 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 2,6-dibromo-N-dodecyldithieno[3,2-b:2',3'-d]pyrrole
  参考文献：
  名称：

  单壁碳纳米管（SWNTs）与含共轭聚合物的双硫杂[3,2- b：2'，3'- d ]吡咯（DTP）的超分子功能化

  摘要：

  芴和二噻吩并[3,2- b：2'，3'- d ]包含共轭聚合物吡咯（DTP），{2,7- [9,9- didodecylfluorene] - ALT -2,6- [ Ñ -dodecyldithieno（ 3,2- b：2'，3'- d）吡咯]}（PF-DTP1）和{2,7- [9,9- didodecylfluorene] - ALT -2,6- [ ñ -3,4,5- （n-十二烷氧基）苯基二硫（3,2- b：2'，3'- d）[吡咯]}（PF-DTP2），已成功使用Suzuki缩聚法合成。这些聚合物具有出色的热稳定性，在Ar下分解温度超过365°C。在DTP单元上引入可溶性侧链，并与可溶性二烷基取代的芴结合，产生了具有新型光电特性的高可溶性聚合物。已经研究了这些含DTP的聚合物与单壁碳纳米管（SWNT）的超分子复合物的形成，并且发现这些聚合物可以形成牢固的超分子聚合物-纳米管组装体

  DOI：

  10.1021/ma201610y

文献信息

• ORGANIC SEMICONDUCTOR MATERIAL, PREPARATION METHODS AND USES THEREOF
  申请人：Zhou Mingjie

  公开号：US20130253151A1

  公开（公告）日：2013-09-26

  Disclosed are organic semiconductor material, preparation methods and uses thereof. The organic semiconductor material is shown as the following formula (P), in which R 1 , R 2 , R 3 , m, n, x and y are defined as the description. The said organic semiconductor material can be used in organic solar cell, organic field effect transistor, organic electroluminescence element, organic optical storage, organic non-linear material or organic laser element.
• Terpyridine-based donor–acceptor metallo-supramolecular polymers with tunable band gaps: Synthesis and characterization
  作者：Fanchao Li、Zhiwei Hu、Hongbing Qiao、Lin Liu、Jiawei Hu、Xuegang Chen、Jie Li

  DOI：10.1016/j.dyepig.2016.04.031

  日期：2016.9

  Three new building blocks containing the electron-donor fused-ring motifs carbazole, dithienosilole (DTS) and dithienopyrrole (DTP) and the 2,2':6',2 ''-terpyridine electron-acceptor motif were designed and synthesized. Directed by transition metal ions, the self-assembly of the building blocks triggered polymerization to form the corresponding metallo-supramolecular polymers PCzTPY, PSiTPY and PNTPY, respectively. The UV-vis absorption maxima of the building blocks occur at long wavelengths (351, 368 and 430 nm for CzTPY, SiTPY and NTPY, respectively), which arises from intramolecular charge transfer (ICT) transitions. However, the absorption maxima of their corresponding metallosupramolecular polymers are clearly red-shifted (to 394, 431 and 509 nm for PCzTPY, PSiTPY and PNTPY, respectively), which is caused by the incorporation of the transition metal ion into the backbones of the target polymers. Based on the above strategies, the resulting metallo-polymers exhibit reduced energy gaps, which are 2.07,1.97 and 1.56 eV for the PCzTPY, PSiTPY and PNTPY metallo-supramolecular polymers, respectively. (C) 2016 Elsevier Ltd. All rights reserved.
• Supramolecular Functionalization of Single-Walled Carbon Nanotubes (SWNTs) with Dithieno[3,2-<i>b</i>:2′,3′-<i>d</i>]pyrrole (DTP) Containing Conjugated Polymers
  作者：Patigul Imin、Mokhtar Imit、Alex Adronov

  DOI：10.1021/ma201610y

  日期：2011.12.13

  soluble dialkyl-substituted fluorene resulted in highly soluble polymers with novel optoelectronic properties. The supramolecular complex formation of these DTP containing polymers with single-walled carbon nanotubes (SWNTs) has been studied, and it was found that these polymers can form strong supramolecular polymer–nanotube assemblies and produce stable complexes in solution. UV–vis–NIR absorption, photoluminescence

  芴和二噻吩并[3,2- b：2'，3'- d ]包含共轭聚合物吡咯（DTP），2,7- [9,9- didodecylfluorene] - ALT -2,6- [ Ñ -dodecyldithieno（ 3,2- b：2'，3'- d）吡咯]}（PF-DTP1）和2,7- [9,9- didodecylfluorene] - ALT -2,6- [ ñ -3,4,5- （n-十二烷氧基）苯基二硫（3,2- b：2'，3'- d）[吡咯]}（PF-DTP2），已成功使用Suzuki缩聚法合成。这些聚合物具有出色的热稳定性，在Ar下分解温度超过365°C。在DTP单元上引入可溶性侧链，并与可溶性二烷基取代的芴结合，产生了具有新型光电特性的高可溶性聚合物。已经研究了这些含DTP的聚合物与单壁碳纳米管（SWNT）的超分子复合物的形成，并且发现这些聚合物可以形成牢固的超分子聚合物-纳米管组装体