N,N'-双(三-p-甲苯基磷酰亚烷基)苯-1,4-二胺 | 51870-56-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N,N'-双(三-p-甲苯基磷酰亚烷基)苯-1,4-二胺
• 英文名称: N1,N4-bis(tri-p-tolylphosphoranylidene) benzene-1,4-diamine
• 英文别名: N,n'-bis(tri-p-tolylphosphoranylidene)benzene-1,4-diamine；tris(4-methylphenyl)-[4-[[tris(4-methylphenyl)-λ5-phosphanylidene]amino]phenyl]imino-λ5-phosphane
• CAS: 51870-56-5
• 化学式: C₄₈H₄₆N₂P₂
• 分子量: 712.854
• InChiKey: BGJWJTLJTUQIEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  245 °C(dec.)
• 沸点：
  809.8±75.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  52
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三对苯甲基膦 、 1,4-二叠氮基苯 以 苯 为溶剂， 以85%的产率得到N,N'-双(三-p-甲苯基磷酰亚烷基)苯-1,4-二胺
  参考文献：
  名称：

  Bis(phosphine Imide)s:  Easily Tunable Organic Electron Donors

  摘要：

  The electrochemical, structural, and spectroscopic properties of bis(phosphine imide)s have been investigated. p-Phenylenebis(phosphine imide)s Ar3PNC6H4NPAr3 (1a-d) have two reversible single-electron oxidations. The first oxidation potentials can be varied from -0.05 to 0.15 V (versus SCE) by modification of the substituents on phosphorus (Ar). Electron-donating substituents lower the oxidation potential, while electron-withdrawing substituents increase the oxidation potential. The difference between the first and second oxidation potential (Delta E, 0.41-0.50) and the electronic coupling (H-ab, 1.1 eV) are similar for 1a-d. Computational (DFT) and UV-visible-NIR spectroscopic investigations of 1a-d suggest that the first oxidation leads to a delocalized radical cation 1a(.+) while the second oxidation leads to a quinonoidal dicationic state 1a(2+). The aromatic linker between phosphine imides has also been modified. Upon oxidation, N,N '-4,4 '-biphenylene(bis(triphenyl)phosphine imide) (3) forms radical cationic and a dicationic species similar to 1a-d. While Delta E (0.18 V) and H-ab (0.63 eV) are smaller, suggesting weaker electronic communication between the two P=N units in the radical cationic state, the presence of NIR absorptions with vibrational fine structure (768, 861, and 983 nm) supports the formation of delocalized radical cation for 3(.+).

  DOI：

  10.1021/jo051196u

文献信息

• Electronic Device and Compound
  申请人：Dorok Sascha

  公开号：US20140182681A1

  公开（公告）日：2014-07-03

  The present invention relates to an electronic device comprising a compound according to formula 1 A-B (1) and wherein —Ar 1 is a C6-C18 arylene, which can be monocyclic or polycyclic and may be optionally substituted by one or more C 1 -C 10 -alkyl or C 3 -C 10 -cycloalkyl groups, —Ar 2 is a C6-C18 arene skeleton, optionally substituted with electron donating groups R 4 , —B 1 and B 2 are independently selected from B and Ar 2 , —B 3 is independently selected from the same group as B, —R 1 , R 2 , R 3 are independently selected from alkyl, arylalkyl, cycloalkyl, aryl, dialkylamino, —x is selected from 0, 1, 2 and 3, wherein for x>1 each Ar 1 may be different, —y is a non-zero integer up to the overall count of valence sites on the arene skeleton, —z is a integer from zero up to the overall count of valence sites on the arene skeleton minus y; as well as a respective compound according to formula A-B.

  本发明涉及一种电子设备，其包含根据式1 A-B（1）的化合物，其中—Ar1是C6-C18芳撑链，可以是单环或多环的，并且可以选择性地被一个或多个C1-C10烷基或C3-C10环烷基取代，—Ar2是C6-C18芳环骨架，可以选择性地被电子给予基团R4取代，—B1和B2是独立地从B和Ar2中选择的，—B3是从与B相同的组中独立选择的，—R1，R2，R3是独立选择的烷基，芳基烷基，环烷基，芳基，二烷基氨基，—x是选择自0、1、2和3，其中对于x>1，每个Ar1可能不同，—y是一个非零整数，最多等于芳环骨架的总价位数，—z是从零到芳环骨架的总价位数减去y的整数；以及根据式A-B的相应化合物。
• IN-SITU CROSS-LINKABLE HOLE TRANSPORTING TRIAZATRUXENE MONOMERS FOR OPTOELECTRONIC DEVICESTR
  申请人：Ecole Polytechnique Fédérale de Lausanne (EPFL)

  公开号：EP3489240A1

  公开（公告）日：2019-05-29

  The invention discloses a polymerizable triazatruxene-based compound of formula (I), an optoelectronic and/or photoelectrochemical device comprising said compound of formula (I) as hole transporting material in hole transport layer under the form of a polymer, and a method of fabrication thereof.

  本发明公开了一种可聚合的式(I)三氮杂环戊烯基化合物、一种包含所述式(I)化合物作为空穴传输层中空穴传输材料的聚合物形式的光电和/或光电化学器件及其制造方法。
• US9502660B2
  申请人：——

  公开号：US9502660B2

  公开（公告）日：2016-11-22
• [EN] ELECTRONIC DEVICE AND COMPOUND<br/>[FR] DISPOSITIF ÉLECTRONIQUE ET COMPOSÉ
  申请人：NOVALED AG

  公开号：WO2012175219A1

  公开（公告）日：2012-12-27

  The present invention relates to an electronic device comprising a compound according to formula 1 A-B (1) and wherein - Ar1 is a C6-C18 arylene, which can be monocyclic or polycyclic and may be optionally substituted by one or more C1-C10-alkyl or C3-C10-cycloalkyl groups, - Ar2 is a C6-C18 arene skeleton, optionally substituted with electron donating groups R4, - B1 and B2 are independently selected from B and Ar2, - B3 is independently selected from the same group as B, - R1, R2, R3 are independently selected from alkyl, arylalkyl, cycloalkyl, aryl, dialkylamino, - x is selected from 0, 1, 2 and 3, wherein for x > 1 each Ar1 may be different, - y is a non-zero integer up to the overall count of valence sites on the arene skeleton, - z is a integer from zero up to the overall count of valence sites on the arene skeleton minus y; as well as a respective compound according to formula A-B.
• Bis(phosphine Imide)s:  Easily Tunable Organic Electron Donors
  作者：Vanina V. Guidi、Zhou Jin、Devin Busse、William B. Euler、Brett L. Lucht

  DOI：10.1021/jo051196u

  日期：2005.9.1

  The electrochemical, structural, and spectroscopic properties of bis(phosphine imide)s have been investigated. p-Phenylenebis(phosphine imide)s Ar3PNC6H4NPAr3 (1a-d) have two reversible single-electron oxidations. The first oxidation potentials can be varied from -0.05 to 0.15 V (versus SCE) by modification of the substituents on phosphorus (Ar). Electron-donating substituents lower the oxidation potential, while electron-withdrawing substituents increase the oxidation potential. The difference between the first and second oxidation potential (Delta E, 0.41-0.50) and the electronic coupling (H-ab, 1.1 eV) are similar for 1a-d. Computational (DFT) and UV-visible-NIR spectroscopic investigations of 1a-d suggest that the first oxidation leads to a delocalized radical cation 1a(.+) while the second oxidation leads to a quinonoidal dicationic state 1a(2+). The aromatic linker between phosphine imides has also been modified. Upon oxidation, N,N '-4,4 '-biphenylene(bis(triphenyl)phosphine imide) (3) forms radical cationic and a dicationic species similar to 1a-d. While Delta E (0.18 V) and H-ab (0.63 eV) are smaller, suggesting weaker electronic communication between the two P=N units in the radical cationic state, the presence of NIR absorptions with vibrational fine structure (768, 861, and 983 nm) supports the formation of delocalized radical cation for 3(.+).