(E)-4,4'-(ethene-1,2-diyl)bis(N,N-bis(4-methoxyphenyl)aniline) | 848153-57-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-4,4'-(ethene-1,2-diyl)bis(N,N-bis(4-methoxyphenyl)aniline)
• 英文别名: (E)-4,4'-bis{bis(4-methoxyphenyl)amino}stilbene；E-4,4'-bis[4-bis(4-methoxyphenyl)amino]stilbene；3,4'-bis[bis(p-methoxyphenyl)amino]stilbene；E,E-4,4'-bis[di(p-anisyl)amino]stilbene；4-[(E)-2-[4-(4-methoxy-N-(4-methoxyphenyl)anilino)phenyl]ethenyl]-N,N-bis(4-methoxyphenyl)aniline
• CAS: 848153-57-1
• 化学式: C₄₂H₃₈N₂O₄
• 分子量: 634.775
• InChiKey: HAVGSGBHMVNTEO-AATRIKPKSA-N

物化性质

• 沸点：
  779.0±60.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-4,4'-(ethene-1,2-diyl)bis(N,N-bis(4-methoxyphenyl)aniline) 在 氯化锑(V) 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以79%的产率得到E,E-4,4'-bis[di(p-anisyl)amino]stilbene bis(hexachloroantimonate)
  参考文献：
  名称：

  Isolation and Crystal Structures of Two Singlet Bis(Triarylamine) Dications with Nonquinoidal Geometries

  摘要：

  We report the first structural data for bis(diarylamine) "bipolarons": we have isolated and crystallographically characterized salts of the dications obtained by two-electron oxidation of E-4,4'-bis[di(p-anisyl)amino]stilbene and EE-2,5-bis{4-[di(p-anisyi)amino]styryl}-3,4-di(n-butoxy)thiophene, [1](2+) and [2](2+) respectively. ESR, NMR, and magnetometry suggest both species have singlet ground states. X-ray structures, together with H-1 NMR coupling constants for [2](2+), indicate geometries in which the bond lengths are shifted toward a quinoidal pattern relative to that in the neutral species, but not to a fully quinoidal extent. In particular, the bond-length alternations across the vinylene bridging groups approach zero. DFT calculations with closed-shell singlet configurations reproduce the observed structures well. Our results indicate that singlet species for which one might expect quinoidal geometries (with differences of ca. 0.1 A between formally single and double bonds) on the basis of a limiting valence-bond representation of the structure can, in fact, show structures with significantly different patterns of bond lengths.

  DOI：

  10.1021/ja0541534
• 作为产物：
  描述：

  3-溴苯乙烯 在 palladium diacetate 、 tris-(dibenzylideneacetone)dipalladium(0) 三乙胺 、 三(邻甲基苯基)磷 、 sodium t-butanolate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 14.0h， 生成 (E)-4,4'-(ethene-1,2-diyl)bis(N,N-bis(4-methoxyphenyl)aniline)
  参考文献：
  名称：

  3,4^′-Bis[bis(t-butyl- and methoxy-phenyl)amino]stilbene Bis(cation radical)s and Their Electrochemical and Magnetic Properties

  摘要：

  合成了3,4'-双[双(p-叔丁基苯基)氨基]斯蒂尔本1a和3,4'-双[双(p-甲氧基苯基)氨基]斯蒂尔本1b。对1的氧化反应进行了电化学测量分析，结果显示通过双电子转移反应可逆生成双(阳离子自由基)2。使用NOBF4进行的化学氧化也得到了双(阳离子自由基)2；UV/可见光和ESR光谱支持铵自由基的形成，且没有任何副反应。双自由基的磁化、磁导率及ESR信号ΔMs = ±2表明其具有较大的三重态-单重态能量间隙。

  DOI：

  10.1246/bcsj.73.1021

文献信息

• Intervalence Transitions in the Mixed-Valence Monocations of Bis(triarylamines) Linked with Vinylene and Phenylene−Vinylene Bridges
  作者：Stephen Barlow、Chad Risko、Sung-Jae Chung、Neil M. Tucker、Veaceslav Coropceanu、Simon C. Jones、Zerubba Levi、Jean-Luc Brédas、Seth R. Marder

  DOI：10.1021/ja054136e

  日期：2005.12.1

  hexachloroantimonate. The intervalence charge-transfer (IVCT) band of 1(+) is narrow and asymmetric and exhibits only weak solvatochromism. Analysis of this band indicates that 1(+) is a class-III or class-II/III borderline mixed-valence species. In contrast, a broad, strongly solvatochromic IVCT band is observed for 2(+), indicating that this species is a class-II mixed-valence species. The assignment

  (E)-4,4'-双[双(4-甲氧基苯基)氨基]二苯乙烯，1，(E,E)-1,4-双[4-[双(4-甲氧基苯基)氨基]苯乙烯基]苯， 2，和两个更长的同系物，(E,E,E)-4,4'-双[4-[双(4-甲氧基苯基)氨基]苯乙烯基]二苯乙烯，3和(E,E,E,E)- 1,4-双(4-[4-[双(4-甲氧基苯基)氨基]苯乙烯基]苯乙烯基)苯, 4, 已被三(4-溴苯基) 六氯锑酸盐氧化成单和二价。1(+) 的间隔电荷转移 (IVCT) 带窄且不对称，仅表现出微弱的溶剂化变色。对该条带的分析表明 1(+) 是 III 类或 II/III 类临界混合价物种。相比之下，对于 2(+) 观察到一个宽的、强溶剂化变色的 IVCT 带，表明该物种是 II 类混合价物种。将 1(+) 和 2(+) 指定为对称的 III 类和不对称的 II 类物种，AM1 计算也支持。1(+) 和 2(+) 的 IVCT 带的静寂分析给出了更大的电子耦合
• A mixed-valence bis(diarylamino)stilbene: crystal structure and comparison of electronic coupling with biphenyl and tolane analogues
  作者：Stephen Barlow、Chad Risko、Veaceslav Coropceanu、Neil M. Tucker、Simon C. Jones、Zerubba Levi、Viktor N. Khrustalev、Mikhail Yu. Antipin、Tiffany L. Kinnibrugh、Tatiana Timofeeva、Seth R. Marder、Jean-Luc Brédas

  DOI：10.1039/b415018j

  日期：——

  The E-4,4′-bis[di(p-anisyl)amino]stilbene cation is a class-III mixed-valence species with electronic coupling comparable to that in its biphenyl-bridged analogue, whereas its tolane-bridged analogue belongs to class II.

  E-4,4'-双[二(对茴香基)氨基]芪阳离子是III类混合价物质，其电子耦合与其联苯桥类似物相当，而其甲苯桥类似物属于第二类。
• Efficient Hole Transporting Materials with Two or Four <i>N</i> , <i>N</i> ‐Di(4‐methoxyphenyl)aminophenyl Arms on an Ethene Unit for Perovskite Solar Cells
  作者：Hyeju Choi、Kwangseok Do、Sojin Park、Jong‐Sung Yu、Jaejung Ko

  DOI：10.1002/chem.201502741

  日期：2015.11.2

  Novel steric bulky hole transporting materials (HTMs) with two or four N,N‐di(4‐methoxyphenyl)aminophenyl units have been synthesized. When the EtheneTTPA was used as a hole transporting material in perovskite solar cell, the power conversion efficiency afforded 12.77 % under AM 1.5 G illumination, which is comparable to the widely used spiro‐OMeTAD based solar cell (13.28 %).

  合成了具有两个或四个N，N-二（4-甲氧基苯基）氨基苯基单元的新型空间大空穴传输材料（HTM）。当将EtheneTTPA用作钙钛矿型太阳能电池的空穴传输材料时，在AM 1.5 G光照下，功率转换效率为12.77％，可与广泛使用的基于spiro-OMeTAD的太阳能电池相媲美（13.28％）。
• NOVEL COMPOUND, AND COMPOSITION FOR FORMING HOLE TRANSPORTING LAYER FOR PEROVSKITE SOLAR CELLS
  申请人：TOKYO CHEMICAL INDUSTRY CO., LTD.

  公开号：US20210319957A1

  公开（公告）日：2021-10-14

  Provided are: a composition for forming a hole transporting layer for perovskite solar cells, which is inexpensive and does not need to be used together with a dopant; and a compound which can be contained in a composition for forming a hole transporting layer. A compound represented by general formula (I) (wherein Ar represents an aryl group; A represents a structure represented by formula (II); Z's independently represent a hydrogen atom, a structure represented by general formula (III), or a structure represented by formula (IV), and maybe the same as or different from each other, wherein a case where each of Z's is a hydrogen atom is excluded; Y's independently represents at least one member selected from the group mentioned below; R 1 and R 2 independently represents a hydrogen atom, an alkyl group or an alkoxy group, or R 1 and R 2 may together form a ring having one or two oxygen atoms; ×'s independently represent an alkyl group, an alkoxy group, an alkylthio group, a monoalkylamino group or a dialkylamino group each of which may be substituted by a halogen atom; k represents 0 or 1; l represents 2 or 3; m represents an integer of 1 to 6; and r represents 1 or 2; wherein, when k is 0, 1 is 3, m is 1 and all of three bonds of A are bonded to Z.
• 3,4^′-Bis[bis(<b><i>t</i></b>-butyl- and methoxy-phenyl)amino]stilbene Bis(cation radical)s and Their Electrochemical and Magnetic Properties
  作者：Tsuyoshi Michinobu、Eishun Tsuchida、Hiroyuki Nishide

  DOI：10.1246/bcsj.73.1021

  日期：2000.4

  3,4′-Bis[bis(p-t-butylphenyl)amino]stilbene 1a and 3,4′-bis[bis(p-methoxyphenyl)amino]stilbene 1b were synthesized. The oxidation of 1 was analyzed by electrochemical measurements, which revealed the reversible formation of the bis(cation radical) 2 via a two-electron transfer reaction. The chemical oxidation of 1 with NOBF4 also gave the bis(cation radical) 2; UV/vis and ESR spectroscopies supported aminium radical formation without any side reaction. Magnetization, magnetic susceptibility, and the ESR ΔMs = ±2 signal of the biradicals indicated triplet ground states with a large triplet-singlet energy gap.

  合成了3,4'-双[双(p-叔丁基苯基)氨基]斯蒂尔本1a和3,4'-双[双(p-甲氧基苯基)氨基]斯蒂尔本1b。对1的氧化反应进行了电化学测量分析，结果显示通过双电子转移反应可逆生成双(阳离子自由基)2。使用NOBF4进行的化学氧化也得到了双(阳离子自由基)2；UV/可见光和ESR光谱支持铵自由基的形成，且没有任何副反应。双自由基的磁化、磁导率及ESR信号ΔMs = ±2表明其具有较大的三重态-单重态能量间隙。