2-((6-(噻吩-2-基)己基)氧基)四氢-2H-吡喃 | 1008131-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 中文名称: 2-((6-(噻吩-2-基)己基)氧基)四氢-2H-吡喃
• 英文名称: 2-((6-(thiophen-2-yl)hexyl)oxy)tetrahydro-2H-pyran
• 英文别名: 2-(6-(thiophen-2-yl)hexyloxy)tetrahydro-2H-pyran；2-(6-thiophen-2-ylhexoxy)oxane
• CAS: 1008131-98-3
• 化学式: C₁₅H₂₄O₂S
• 分子量: 268.42
• InChiKey: AUOKBWWBIJKXTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-((6-(噻吩-2-基)己基)氧基)四氢-2H-吡喃 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 正丁基锂 、 偶氮二甲酸二异丙酯 、 potassium carbonate 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 氯仿 、 水 、 甲苯 为溶剂， 反应 48.0h， 生成 bis(6-(5-(7-(5-bromothiophen-2-yl)benzo[c][1,2,5]thiadiazol-4-yl)thiophen-2-yl)hexyl) isophthalate
  参考文献：
  名称：

  基于以苯并二噻吩为中心的A–D–A型共轭链段和与二羧酸酯连接的烷基非共轭链段的光伏聚（棒状线圈）聚合物†

  摘要：

  与经过深入研究的光伏共轭聚合物和小分子化合物不同，聚（棒-螺旋）聚合物正在作为一类新型的光伏材料出现。由于它们以替代方式由确定的共轭和非共轭链段组成，因此这种材料有望兼具小分子化合物和共轭聚合物的优点。基于以苯并二噻吩为中心的受体-供体-受体（AD）共轭链段和二羧酸酯连接的烷基非共轭链段，本研究新设计并合成了两种聚（棒-螺旋）聚合物。与三种先前报道的类似物一起，对这些聚合物的光伏性能进行了系统的研究，特别注意非共轭链段中的二羧酸酯连接单元和刚性共轭链段上的烷基侧链的作用。发现前一个因素影响很小，而后一个因素对材料的大多数与膜有关的特性具有重大影响，包括膜吸收光谱，前沿轨道能级，带隙，原始和光伏共混膜的微观结构和形态以及空穴迁移率。经过优化后，基于该系列聚合物的体异质结有机太阳能电池的功率转换效率为0.4-1.09％。包括薄膜吸收光谱，前沿轨道能级，带隙，原始和光伏混合物薄膜的微观结构和形态

  DOI：

  10.1039/c6ra01200k

文献信息

• Discrete Photopatternable π-Conjugated Oligomers for Electrochromic Devices
  作者：Christian B. Nielsen、Alex Angerhofer、Khalil A. Abboud、John R. Reynolds

  DOI：10.1021/ja7112273

  日期：2008.7.1

  Three discrete oligomeric systems including an all-thiophene (T6) system, a thiophene/phenylene (TPTTPT) system, and a thiophene/EDOT/phenylene (TPEEPT) system have been constructed and characterized with emphasis on structural, optical, electrochemical, and spectroelectrochemical properties. For all three chromophores, the radical cation, the dication, and the 7r-dimer have been identified and characterized. EPR spectroscopy reveals that the radical cations of TPTTPT and TPEEPT have g values of 2.008-2.012 and peak-to-peak widths in the range 4.2-5.3 G. Formation of the radical cation takes place at a lower potential for TPEEPT than for TPTTPT and T6, whereas subsequent oxidation to the dication occurs more easily for TPTTPT than for TPEEPT and T6. We ascribe this observation to more localized charges in the oxidized species of TPEEPT, which is supported by our finding that the radical cation of TPEEPT is less prone to undergo 7r-dimerization than the radical cations of TPTTPT and T6. All the oxidized species are sufficiently stable to allow for optical characterization, and the relative positions of all absorption bands are found to be in agreement with the electrochemical data. For further solid-state modifications of these materials, we have effectively modified the synthetic design and grafted terminal functionalities (e.s. acrylates) onto the discrete oligorners. Of these novel materials, TPEEPT proves to be the most promising anodically coloring material for electrochromics, and it undergoes reversible switching between two different colored states (bright yellow and clear blue) and one almost transparent and color neutral state. Contrast ratios, measured as 0%Tat Amax, are as high as 62.5%, and switching times are in the range 2-5 s for the coloration process, though significantly longer for the bleaching process. As a proof of concept, we have successfully constructed a simple photopatterned electrochromic device by exploiting the terminal acrylate functionalities of the oligomers in a UV-initiated cross-linking process. To the best of our knowledge, this is the first oligomer-based photopatterned electrochromic device reported in the literature.