N,N,N′,N′-tetraphenyloxalamide | 109124-48-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N,N′,N′-tetraphenyloxalamide
• 英文别名: TPEA；Tetraphenyloxamid；tetraphenyl-oxalamide；Tetraphenyl-oxalamid；Oxalsaeure-bis-diphenylamid；Tetraphenyloxalamid；N,N,N',N'-tetraphenyloxamide
• CAS: 109124-48-3
• 化学式: C₂₆H₂₀N₂O₂
• 分子量: 392.457
• InChiKey: VZCWTKRRHMAIJV-UHFFFAOYSA-N

物化性质

• 熔点：
  169 °C
• 沸点：
  541.5±33.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N-二苯基氨基甲酸乙酯 在 sodium 作用下， 以 苯 为溶剂， 反应 1.0h， 以49%的产率得到N,N,N′,N′-tetraphenyloxalamide
  参考文献：
  名称：

  Sodium metal-promoted condensations of carbamates

  摘要：

  DOI：

  10.1021/jo00392a042

文献信息

• Stolle, Chemische Berichte, 1916, vol. 49, p. 3916
  作者：Stolle

  DOI：——

  日期：——
• CRUMRINE, D. S.;DIESCHBOURG, T. A.;OTOOLE, J. G.;TASSONE, B. A.;VANDEBURG+, J. ORG. CHEM., 52,(1987) N 16, 3699-3701
  作者：CRUMRINE, D. S.、DIESCHBOURG, T. A.、OTOOLE, J. G.、TASSONE, B. A.、VANDEBURG+

  DOI：——

  日期：——
• Self‐Aggregated Light‐Trapping Nanodots for Highly Efficient Organic Solar Cells
  作者：Huaizhi Gao、Runnan Yu、Yongshuai Gong、Zongwen Ma、Zhangwei He、Yiman Dong、Kunxiang Xu、Yiming Bai、Zhan'ao Tan

  DOI：10.1002/smll.202205128

  日期：2022.12

  The typical thickness of the photoactive layer in organic solar cells (OSCs) is around 100 nm, which limits the absorption efficiency of the incident light and the power conversion efficiency (PCE) of OSCs. Therefore, light‐trapping schemes to reduce the optical losses in the thin photoactive layers are critically important for efficient OSCs. Herein, light‐trapping and electron‐collection dual‐functional small organic molecules, N,N,N′,N′‐tetraphenyloxalamide (TPEA) and N,N,N′,N′‐tetraphenylmalonamide (TPMA), are designed and synthesized by a one‐step acylation reaction. Driven by strong intermolecular force, TPEA and TPMA tend to self‐aggregate into hemispherical light‐trapping nanodots on the photoactive layer, resulting in enhanced light harvesting. Meanwhile, TPEA and TPMA demonstrate high electron mobility and excellent electron‐collection ability.  Compared with the device without cathode buffer layer (CBL, PCE = 14.09%), PM6:BTP‐eC9 based OSCs with TPEA and TPMA light‐trapping CBLs demonstrate greatly enhanced PCE of 16.21% and 17.85%, respectively. Furthermore, a record PCE of 19.02% can be achieved for PM6:BTP‐eC9:PC₇₁BM based ternary OSC with TPMA light‐trapping CBL. Moreover, TPMA exhibits a low synthesis cost of only 0.61 $ g⁻¹ with high yield. These findings could open a window for the rational design of multifunctional CBLs for efficient and stable OSCs.
• Sodium metal-promoted condensations of carbamates
  作者：David S. Crumrine、Thomas A. Dieschbourg、James G. O'Toole、Benjamin A. Tassone、Suzanne C. Vandeburg

  DOI：10.1021/jo00392a042

  日期：1987.8