5-diphenylamino-2,2'-bithiophene | 554416-50-1

• 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: 5-diphenylamino-2,2'-bithiophene
• 英文别名: 5-diphenylamino-2,2'-dithiophene；N,N-(5-diphenylamino)[2,2-bithiophene]；[2,2'-Bithiophen]-5-amine, N,N-diphenyl-；N,N-diphenyl-5-thiophen-2-ylthiophen-2-amine
• CAS: 554416-50-1
• 化学式: C₂₀H₁₅NS₂
• 分子量: 333.478
• InChiKey: LPXMKNKGYLMANQ-UHFFFAOYSA-N

物化性质

• 熔点：
  72 °C
• 沸点：
  486.0±35.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  23
• 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：
  59.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-diphenylamino-2,2'-bithiophene 生成 2,2'-bis(diphenylamino)-5,5'-bis(2-thienyl)-3,3'-bithiophene
  参考文献：
  名称：

  由2-二苯基氨基噻吩低聚物衍生的自由基阳离子的各种反应

  摘要：

  2-二苯基氨基取代的低聚噻吩8 m的ESR光谱电化学测量证明了氧化后自由基阳离子8m +的存在。它们的稳定性和二聚化很大程度上取决于噻吩单元的数量m。自由基阳离子81+和82+具有很高的反应性，并自发二聚，从而生成2,5-双（二苯基氨基）-2,2'-联噻吩10 2或2,5-双（二苯基氨基）-5,5'-双（2-噻吩基）-3，3′-位硫烷11 2。相反，自由基阳离子83 + –85 +非常稳定，根本不二聚。

  DOI：

  10.1016/j.tetlet.2006.08.074
• 作为产物：
  描述：

  2-溴噻吩 、 2-diphenylaminothiophene 在 四(三苯基膦)钯 正丁基锂 、 三丁基氯化锡 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 8.0h， 以40%的产率得到5-diphenylamino-2,2'-bithiophene
  参考文献：
  名称：

  Stille Coupling of 2-Diarylaminothiophenes with Mono- and Di­bromo(het)arylenes

  摘要：

  N,N-二芳基取代的2-氨基噻吩3通过与几种溴苯5和2-溴噻吩6在钯催化下的交叉偶联反应，经由2-(N,N-二芳基氨基)-5-锡基噻吩4，被转化为N,N-二芳基取代的2-氨基-5-苯基噻吩7和5-氨基-2,2'-联噻吩9，以及转化为N,N'-全芳基取代的5,5'-二氨基-2,2'-联噻吩8及其苯ylene和噻吩ylene类似物10-13。

  DOI：

  10.1055/s-2005-861804

文献信息

• On the protonation and deuteration of <i>N</i> , <i>N</i> ‐disubstituted 2‐aminothiophenes, 2‐aminothiazoles, and some 3‐amino substituted analogues
  作者：Christoph Heichert、Horst Hartmann

  DOI：10.1002/jhet.4279

  日期：2021.7

  In contrast to their carbocyclic aniline analogues, N,N-diarylsubtituted 2-aminothiophenes are not protonated at their N-atoms but at the 5-position or, to a smaller extent, at the 3-position of the thiophene nucleus giving rise to cationic species of the Wheland type. However, 5-formyl and 5-acetyl-substituted 2-(N,N-diarylamino)thiophenes are protonated at the corresponding carbonyl moieties. This

  与它们的碳环苯胺类似物相比，N , N - 二芳基取代的 2-氨基噻吩不在它们的N -原子处质子化，而是在 5-位，或者在较小程度上，在噻吩核的 3-位产生阳离子惠兰型的物种。然而，5-甲酰基和5-乙酰基取代的2-( N，N-二芳基氨基)噻吩在相应的羰基部分被质子化。这一发现不仅有助于深入了解N , N -二取代 2-氨基噻吩的亲电取代机制，而且还允许通过用 CF 3处理其非氘化母体化合物来制备氘化 2-氨基噻吩酷。
• New molecular materials for hole injection: the synthesis and in situ ESR-UV/Vis/NIR spectroelectrochemistry of 2-diarylaminothiophene-based starburst compounds
  作者：Peter Rapta、Ahacene Tabet、Horst Hartmann、Lothar Dunsch

  DOI：10.1039/b711328e

  日期：——

  A series of 2-diarylaminothiophene-based starburst compounds 14–16 with a central triphenylamino-, benzene-, and 1,3,5-triphenylbenzene moiety, respectively, were prepared at moderate yields by a palladium-catalysed coupling reaction. Their electrochemical, optical and magnetic properties were studied with respect to their application as hole transport materials, using cyclic voltammetry and in situ ESR-UV/Vis/NIR spectroelectrochemistry. Although all prepared 2-diarylaminothiophene-based starburst compounds are structurally related, their electrochemical properties differ in their dependence on the central moiety. The number of reversible voltammetric peaks is diminished upon changing the central triphenylamino moiety of the starburst compounds to a central benzene or 1,3,5-triphenylbenzene moiety. The simultaneous multiple electron transfer as well as the location of the spins on the core moieties was detected in the oxidation of the 1,3,5-triphenylbenzene based starburst compound. The stability of the charged states increased substantially upon the incorporation of a thiophene moiety between the central moieties and the side groups.

  通过钯催化偶联反应，以中等产率制备了一系列 2-二芳基氨基噻吩基星爆化合物 14-16，其中心分别具有三苯胺、苯和 1,3,5- 三苯基苯分子。利用循环伏安法和原位 ESR-UV/Vis/NIR 光谱电化学法研究了它们作为空穴传输材料的电化学、光学和磁学特性。尽管所有制备的基于 2-二芳基氨基噻吩的星状化合物在结构上都是相关的，但它们的电化学性质却因中心分子的不同而不同。将星爆化合物的中心三苯胺分子改为中心苯分子或 1,3,5- 三苯基苯分子后，可逆伏安峰的数量会减少。在 1,3,5-三苯基苯基星爆化合物的氧化过程中，检测到了多个电子同时转移以及自旋在核心分子上的位置。在中心分子和侧基之间加入噻吩分子后，带电状态的稳定性大大提高。
• Preparation and Characterization of α,α‘-Bisdiarylamino-Capped Oligothiophenes
  作者：Ahcene Tabet、Anke Schröder、Horst Hartmann、Dirk Rohde、Lothar Dunsch

  DOI：10.1021/ol034322u

  日期：2003.5.1

  A series of alpha,alpha'-bisdiarylamino-capped oligothiophenes C-n were prepared by the palladium-catalyzed reaction of the dibromo compounds A(i) with diarylamines, N,N-diarylamino-substituted thiophenes or 2,2'-bithiophenes BXj These easily oxidizable compounds exhibit a high tendency to form amorphous glasses and characteristic electrochemical and spectroscopic properties that depend significantly on the number of their thiophene moieties.
• Stille Coupling of 2-Diarylaminothiophenes with Mono- and Di­bromo(het)arylenes
  作者：Horst Hartmann、Ahcene Tabet

  DOI：10.1055/s-2005-861804

  日期：——

  N,N-Diaryl-substituted 2-aminothiophenes 3 have been transformed by reaction with several bromobenzenes 5 and 2-bromothiophenes 6 in a palladium catalysed cross-coupling reaction, via 2-(N,N-diarylamino)-5-stannyl-thiophenes 4, into N,N-diaryl-substituted 2-amino-5-phenylthiophenes 7 and 5-amino-2,2′-bi­thiophenes 9 as well as into N,N′-peraryl-substituted 5,5′-diamino-2,2′-bithiophenes 8 and their phenylene and thienylene homologues 10-13.

  N,N-二芳基取代的2-氨基噻吩3通过与几种溴苯5和2-溴噻吩6在钯催化下的交叉偶联反应，经由2-(N,N-二芳基氨基)-5-锡基噻吩4，被转化为N,N-二芳基取代的2-氨基-5-苯基噻吩7和5-氨基-2,2'-联噻吩9，以及转化为N,N'-全芳基取代的5,5'-二氨基-2,2'-联噻吩8及其苯ylene和噻吩ylene类似物10-13。
• The variety of reactions of radical cations derived from 2-diphenylaminothiophene oligomers
  作者：Peter Rapta、Dirk Rohde、Horst Hartmann、Lothar Dunsch

  DOI：10.1016/j.tetlet.2006.08.074

  日期：2006.10

  existence of radical cations 8m+ upon oxidation. Their stability and dimerization depend significantly on the number m of thiophene units. The radical cations 81+ and 82+ are very reactive and dimerize spontaneously to yield either 2,5-bis(diphenylamino)-2,2′-bithiophene 102 or 2,5-bis(diphenylamino)-5,5′-bis(2-thienyl)-3,3′-bithiopene 112, respectively. In contrast, the radical cations 83+–85+ are

  2-二苯基氨基取代的低聚噻吩8 m的ESR光谱电化学测量证明了氧化后自由基阳离子8m +的存在。它们的稳定性和二聚化很大程度上取决于噻吩单元的数量m。自由基阳离子81+和82+具有很高的反应性，并自发二聚，从而生成2,5-双（二苯基氨基）-2,2'-联噻吩10 2或2,5-双（二苯基氨基）-5,5'-双（2-噻吩基）-3，3′-位硫烷11 2。相反，自由基阳离子83 + –85 +非常稳定，根本不二聚。