2,5-Dibromo-3-[5-(3,6,7,10,11-pentapentoxytriphenylen-2-yl)oxypentyl]thiophene | 1558672-78-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2,5-Dibromo-3-[5-(3,6,7,10,11-pentapentoxytriphenylen-2-yl)oxypentyl]thiophene
• 英文别名: 2,5-dibromo-3-[5-(3,6,7,10,11-pentapentoxytriphenylen-2-yl)oxypentyl]thiophene
• CAS: 1558672-78-8
• 化学式: C₅₂H₇₂Br₂O₆S
• 分子量: 985.014
• InChiKey: UBHVKPABQGOAOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.6
• 重原子数：
  61
• 可旋转键数：
  32
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,5-Dibromo-3-(5-bromopentyl)thiophene 、 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-[5-(3,6,7,10,11-pentapentoxytriphenylen-2-yl)oxypentyl]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

文献信息

• Intertwined Lamello-Columnar Coassemblies in Liquid-Crystalline Side-Chain Π-Conjugated Polymers: Toward a New Class of Nanostructured Supramolecular Organic Semiconductors
  作者：Danli Zeng、Ibtissam Tahar-Djebbar、Yiming Xiao、Farid Kameche、Navaphun Kayunkid、Martin Brinkmann、Daniel Guillon、Benoît Heinrich、Bertrand Donnio、Dimitri A. Ivanov、Emmanuelle Lacaze、David Kreher、Fabrice Mathevet、André-Jean Attias

  DOI：10.1021/ma4020356

  日期：2014.3.11

  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.