3-[(10-bromo)decyl]-2,5-dibromothiophene | 503311-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-[(10-bromo)decyl]-2,5-dibromothiophene
• 英文别名: 2,5-dibromo-3-(10-bromodecyl)thiophene
• CAS: 503311-30-6
• 化学式: C₁₄H₂₁Br₃S
• 分子量: 461.099
• InChiKey: NWRABPIWVFGDLU-UHFFFAOYSA-N

物化性质

• 沸点：
  432.2±40.0 °C(Predicted)
• 密度：
  1.593±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-[(10-bromo)decyl]-2,5-dibromothiophene 、 2-hydroxy-3,6,7,10,11-pentapentyloxytriphenylene 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,5-Dibromo-3-[10-(3,6,7,10,11-pentapentoxytriphenylen-2-yl)oxydecyl]thiophene
  参考文献：
  名称：

  Intertwined Lamello-Columnar Coassemblies in Liquid-Crystalline Side-Chain Π-Conjugated Polymers: Toward a New Class of Nanostructured Supramolecular Organic Semiconductors

  摘要：

  A set of liquid-crystalline polymeric systems, associating at once the regioregular polythiophene backbone and pending mesogenic triphenylenes, is reported. Two series, namely regular homopolymers and alternating copolymers, were prepared by adapting a Grignard metathesis-based methodology, allowing some of the relevant structural parameters to be sequentially and independently modified. The thermal and self-organization behaviors of these uncommon macromolecular systems were investigated by polarized-light optical microscopy, differential scanning calorimetry and temperature-dependent small-angle X-ray scattering. Most polymers self-organize into mesophases possessing intertwined lamello-columnar morphologies, resulting from the simultaneous coexistence of lamellar and columnar sublattices. The successful preparation of oriented thin films of several of these polymeric homologues allowed further investigations by atomic force microscopy, transmission electron microscopy, electron diffraction, and grazing-incidence SAXS, which provided a deeper insight of the intricate supramolecular organizational modes, including the complete elucidation of the structure of the lamello-columnar mesophases. This simple and versatile strategy provides a route to elaborate polymeric materials incorporating two intercalated separate pathways toward charge carrier transport, of paramount importance for future electronic and optoelectronic applications.

  DOI：

  10.1021/ma4020356
• 作为产物：
  描述：

  1,10-二溴癸烷 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[(10-bromo)decyl]-2,5-dibromothiophene
  参考文献：
  名称：

  Intertwined Lamello-Columnar Coassemblies in Liquid-Crystalline Side-Chain Π-Conjugated Polymers: Toward a New Class of Nanostructured Supramolecular Organic Semiconductors

  摘要：

  A set of liquid-crystalline polymeric systems, associating at once the regioregular polythiophene backbone and pending mesogenic triphenylenes, is reported. Two series, namely regular homopolymers and alternating copolymers, were prepared by adapting a Grignard metathesis-based methodology, allowing some of the relevant structural parameters to be sequentially and independently modified. The thermal and self-organization behaviors of these uncommon macromolecular systems were investigated by polarized-light optical microscopy, differential scanning calorimetry and temperature-dependent small-angle X-ray scattering. Most polymers self-organize into mesophases possessing intertwined lamello-columnar morphologies, resulting from the simultaneous coexistence of lamellar and columnar sublattices. The successful preparation of oriented thin films of several of these polymeric homologues allowed further investigations by atomic force microscopy, transmission electron microscopy, electron diffraction, and grazing-incidence SAXS, which provided a deeper insight of the intricate supramolecular organizational modes, including the complete elucidation of the structure of the lamello-columnar mesophases. This simple and versatile strategy provides a route to elaborate polymeric materials incorporating two intercalated separate pathways toward charge carrier transport, of paramount importance for future electronic and optoelectronic applications.

  DOI：

  10.1021/ma4020356

文献信息

• Self-Organized Hole Transport Layers Based on Polythiophene Diblock Copolymers for Inverted Organic Solar Cells with High Efficiency
  作者：Kai Yao、Lie Chen、Xun Chen、Yiwang Chen

  DOI：10.1021/cm400297p

  日期：2013.3.26

  Novel fluoroalkyl side-chain diblock copolymers, poly(3-hexylthiophene)-block-poly[3-(4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyloxy)phenyl)-decyloxy)thiophene] (P3HT-b-P3FAT), were successfully synthesized by Grignard metathesis (GRIM) polymerization. Driven by the low surface energy of fluoroalkyl side chains, the fluorinated polymers can spontaneously segregate on the surface of poly-(3-hexylthiophene) (P3HT) during spin-coating processes. As the P3HT block increases in the copolymer, higher concentrations of fluoropolymers are required to form the self-assembled monolayer on the surface. The fluorinated part forms an interfacial dipole that shifts the work function of the anode metal, while the P3HT block can interact with the P3HT donor for hole transport. With this self-assembly hole transport layer to align the energy levels, P3HT:PCBM photovoltaic devices are easily fabricated to achieve improved performance. Overall, devices prepared with 1.5 mg mL(-1) copolymer PFT-3HT with a 3:1 ratio of P3HT to P3FAT block in the active layer solution displayed PCE values of up to 4.6% (50% PCE increase over a PEDOT:PSS control device) and showed a significant long-term stability in excess of 300 h in air.