4-(2,2’-bithiophen-5-yl)-3,5-dimethyl-1H-pyrazole | 1616780-44-9

• 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: 4-(2,2’-bithiophen-5-yl)-3,5-dimethyl-1H-pyrazole
• 英文别名: 4-([2,2'-bithiophen]-5-yl)-3,5-dimethyl-1H-pyrazole；4-[5-(2,2'-bithienyl)]-3,5-dimethyl-1H-pyrazole；3,5-dimethyl-4-(5-thiophen-2-ylthiophen-2-yl)-1H-pyrazole
• CAS: 1616780-44-9
• 化学式: C₁₃H₁₂N₂S₂
• 分子量: 260.384
• InChiKey: BFYCTDNUMFNMIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  85.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,2’-bithiophen-5-yl)-3,5-dimethyl-1H-pyrazole 、 3,5-bis(octyloxy)benzoic acid 以 四氢呋喃 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  由吡唑/苯甲酸衍生物生成的氢键杆-线圈二嵌段配合物的柱状液晶自组装

  摘要：

  通过结合联噻吩共轭的吡唑衍生物和烷氧基取代的苯甲酸衍生物，我们合成了具有刚性杆和柔性线圈的氢键杆-线圈二嵌段配合物。使用偏振光学显微镜，分子模型和液晶（LC）状态下的X射线散射研究了它们的自组装纳米结构。它们根据苯甲酸中烷氧基取代基的数量和长度形成不同类型的超分子LC相。低脂族线圈与棒段（二辛氧基链）的体积比低的二嵌段复合物自组装成层状相；具有较高比率（二十二烷基氧基，三辛氧基和十三烷基氧基链）的体系形成了色谱柱。在这些柱状结构中 两个吡唑和两个苯甲酸通过N–H··O和O–H···N氢键形成芳族四聚体核。然后将被柔性脂族链包围的两组芳族四聚物堆叠以得到柱状相。这些是包含氢键合的吡唑-苯甲酸衍生物和四聚刚性芳香族骨架的超分子LC结构的新实例。

  DOI：

  10.1002/bkcs.10556
• 作为产物：
  描述：

  4-iodo-3,5-dimethyl-1-tosyl-1H-pyrazole 在 甲醇 、 四(三苯基膦)钯 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 21.0h， 生成 4-(2,2’-bithiophen-5-yl)-3,5-dimethyl-1H-pyrazole
  参考文献：
  名称：

  Tuning the Extended Structure and Electronic Properties of Gold(I) Thienyl Pyrazolates

  摘要：

  A series of thienyl pyrazole proligands and gold(l) thienyl pyrazolate cyclic trinuclear complexes (CTCs) have been synthesized. The relationship between the structure and emission properties of bridging thienyl pyrazolates within gold(I) cyclic trinuclear complexes suggests that the nature of dual emission is sensitive to ligand conjugation length. Density functional theory has been used to support the assignment of metal-sensitized, ligand-localized phosphorescence from monothienyl complexes, while low-lying, ligand-localized LUMOs present in bithienyl systems prohibit metal-sensitized phosphorescence. Soluble n-hexyl derivatives have been synthesized to explore the electrochemical properties of gold(I) thienyl pyrazolates CTCs, and conductive electropolymerized thin films were realized.

  DOI：

  10.1021/ic4031365

文献信息

• Synthesis and Self-Assemblies of Bithiophene Functionalized 1H-Pyrazole Derivatives
  作者：Jung Su Park

  DOI：10.5012/bkcs.2014.35.4.1221

  日期：2014.4.20
• Tuning the Extended Structure and Electronic Properties of Gold(I) Thienyl Pyrazolates
  作者：Lyndsey D. Earl、Jeffrey K. Nagle、Michael O. Wolf

  DOI：10.1021/ic4031365

  日期：2014.7.21

  A series of thienyl pyrazole proligands and gold(l) thienyl pyrazolate cyclic trinuclear complexes (CTCs) have been synthesized. The relationship between the structure and emission properties of bridging thienyl pyrazolates within gold(I) cyclic trinuclear complexes suggests that the nature of dual emission is sensitive to ligand conjugation length. Density functional theory has been used to support the assignment of metal-sensitized, ligand-localized phosphorescence from monothienyl complexes, while low-lying, ligand-localized LUMOs present in bithienyl systems prohibit metal-sensitized phosphorescence. Soluble n-hexyl derivatives have been synthesized to explore the electrochemical properties of gold(I) thienyl pyrazolates CTCs, and conductive electropolymerized thin films were realized.
• Columnar Liquid Crystalline Self-Assembly of Hydrogen-Bonded Rod-Coil Diblock Complexes Created from Pyrazole/Benzoic acid Derivatives
  作者：Ho-Joong Kim、Sung Cho、Jung Su Park

  DOI：10.1002/bkcs.10556

  日期：2015.11

  synthesized hydrogen‐bonded rod–coil diblock complexes having both a rigid rod and a flexible coil by combining bithiophene‐conjugated pyrazole derivatives and alkoxy‐substituted benzoic acid derivatives. Their self‐assembled nanostructures were investigated using polarized optical microscopy, molecular modeling, and X‐ray scattering in liquid crystalline (LC) state. They form different types of supramolecular

  通过结合联噻吩共轭的吡唑衍生物和烷氧基取代的苯甲酸衍生物，我们合成了具有刚性杆和柔性线圈的氢键杆-线圈二嵌段配合物。使用偏振光学显微镜，分子模型和液晶（LC）状态下的X射线散射研究了它们的自组装纳米结构。它们根据苯甲酸中烷氧基取代基的数量和长度形成不同类型的超分子LC相。低脂族线圈与棒段（二辛氧基链）的体积比低的二嵌段复合物自组装成层状相；具有较高比率（二十二烷基氧基，三辛氧基和十三烷基氧基链）的体系形成了色谱柱。在这些柱状结构中 两个吡唑和两个苯甲酸通过N–H··O和O–H···N氢键形成芳族四聚体核。然后将被柔性脂族链包围的两组芳族四聚物堆叠以得到柱状相。这些是包含氢键合的吡唑-苯甲酸衍生物和四聚刚性芳香族骨架的超分子LC结构的新实例。