5-azido-5-(3,5-di-tert-butylbenzyl)pyrimidine-2,4,6(1H,3H,5H)-trione | 1245570-48-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-azido-5-(3,5-di-tert-butylbenzyl)pyrimidine-2,4,6(1H,3H,5H)-trione
• 英文别名: 5-Azido-5-[(3,5-ditert-butylphenyl)methyl]-1,3-diazinane-2,4,6-trione
• CAS: 1245570-48-2
• 化学式: C₁₉H₂₅N₅O₃
• 分子量: 371.439
• InChiKey: AVDFNLMYGWRBLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-azido-5-(3,5-di-tert-butylbenzyl)pyrimidine-2,4,6(1H,3H,5H)-trione 、 足球烯 以 氯苯 为溶剂， 反应 48.0h， 以37%的产率得到
  参考文献：
  名称：

  Self-Assembly of Supramolecular Fullerene Ribbons via Hydrogen-Bonding Interactions and Their Impact on Fullerene Electronic Interactions and Charge Carrier Mobility

  摘要：

  The anisotropy of the electronic interactions between fullerenes in crystalline solids was examined using a confocal fluorescence microscope by probing the polarization of the fluorescence emission arising from fullerene excimer-like emitting states. Crystals of Can obtained by vacuum-sublimation or from chloroform solution exhibited no or little polarization (p = 0 or 0.11, respectively), as expected from the high symmetry of the C-60 fcc lattice or the low degree of anisotropy induced by included solvent molecules. The use of hydrogen-bonding to supramolecularly control interfullerene electronic interactions was explored using a fullerene derivative (1) combining a solubilizing 3,4-di-tert-butylbenzene group and a barbituric acid hydrogen-bonding (H-B) moiety. The crystal structure of 1 establishes the existence of fullerene H-B tapes along which interfullerene electronic interactions are expected to be large. In agreement with this, we observe very strong polarization of the fullerene excimer-like emission (p = 0.78), indicative of a high degree of anisotropy in the fullerene interactions. The charge-carrier mobility of 1 as determined from OFET devices was found to be lower than that of C-60 (1.2 x 10(-4) vs 1.2 x 10(-2) cm(2)/s V), which is rationalized on the basis of the reduced dimensionality of 1 as a wire-like semiconductor and variations in the morphology of the device active layer revealed by AFM measurments.

  DOI：

  10.1021/ja104750f
• 作为产物：
  描述：

  5-(3,5-di-tert-butylbenzyl)pyrimidine-2,4,6(1H,3H,5H)-trione 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以92%的产率得到5-azido-5-(3,5-di-tert-butylbenzyl)pyrimidine-2,4,6(1H,3H,5H)-trione
  参考文献：
  名称：

  Self-Assembly of Supramolecular Fullerene Ribbons via Hydrogen-Bonding Interactions and Their Impact on Fullerene Electronic Interactions and Charge Carrier Mobility

  摘要：

  The anisotropy of the electronic interactions between fullerenes in crystalline solids was examined using a confocal fluorescence microscope by probing the polarization of the fluorescence emission arising from fullerene excimer-like emitting states. Crystals of Can obtained by vacuum-sublimation or from chloroform solution exhibited no or little polarization (p = 0 or 0.11, respectively), as expected from the high symmetry of the C-60 fcc lattice or the low degree of anisotropy induced by included solvent molecules. The use of hydrogen-bonding to supramolecularly control interfullerene electronic interactions was explored using a fullerene derivative (1) combining a solubilizing 3,4-di-tert-butylbenzene group and a barbituric acid hydrogen-bonding (H-B) moiety. The crystal structure of 1 establishes the existence of fullerene H-B tapes along which interfullerene electronic interactions are expected to be large. In agreement with this, we observe very strong polarization of the fullerene excimer-like emission (p = 0.78), indicative of a high degree of anisotropy in the fullerene interactions. The charge-carrier mobility of 1 as determined from OFET devices was found to be lower than that of C-60 (1.2 x 10(-4) vs 1.2 x 10(-2) cm(2)/s V), which is rationalized on the basis of the reduced dimensionality of 1 as a wire-like semiconductor and variations in the morphology of the device active layer revealed by AFM measurments.

  DOI：

  10.1021/ja104750f