trans-4-(N-methyl-N-phenylamino)stilbene | 410097-28-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: trans-4-(N-methyl-N-phenylamino)stilbene
• 英文别名: N-methyl-N-phenyl-4-[(E)-2-phenylethenyl]aniline
• CAS: 410097-28-8
• 化学式: C₂₁H₁₉N
• 分子量: 285.389
• InChiKey: YOJDHXBDFXWJSK-OUKQBFOZSA-N

物化性质

• 沸点：
  449.8±25.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trans-4-(N-methyl-N-phenylamino)stilbene 以 四氢呋喃 、 正己烷 为溶剂， 生成 cis-4-(N-methyl-N-phenylamino)stilbene
  参考文献：
  名称：

  Fluorescence Enhancement of trans-4-Aminostilbene by N-Phenyl Substitutions:  The “Amino Conjugation Effect”

  摘要：

  The synthesis, structure, and photochemical behavior of the trans isomers of 4-(N-phenylamino)stilbene (1c), 4-(A methyl-N-phenylamino)stilbene (1d), 4-(NN-diphenylamino)stilbene (le), and 4-(N-(2,6dimethylphenyl)amino)stilbene (1f) are reported and compared to that of 4-aminostilbene (1a) and 4-N,N-dimethylaminostilbene (1b). Results for the corresponding 3-styrylpyridine (2) and 2-styrylnaphthalene analogues (3) are also included. The introduction of N-phenyl substituents to 4-aminostilbenes leads to a more planar ground-state geometry about the nitrogen atom, a red shift of the absorption and fluorescence spectra, and a less distorted structure with a larger charge-transfer character for the fluorescent excited state. Consequently, the N-phenyl derivatives 1c-e have low photoisomerization quantum yields and high fluorescence quantum yields at room temperature, in contrast to the behavior of la, 1b, and most unconstrained monosubstituted trans-stilbenes. The isomerization of 1c and 1d is a singlet-state process, whereas it is a triplet-state process for le, presumably due to a relatively higher singlet-state torsional barrier. The excited-state behavior of 1f resembles 1a and 1b instead of 1c-e as a consequence of the less planar amine geometry and weaker orbital interactions between the N-phenyl and the aminostilbene groups. Such an N-phenyl substituent effect is also found for 2 and 3 and thus appears to be general for stilbenoid systems. The nature of this effect can be described as an ''amino conjugation effect''.

  DOI：

  10.1021/ja016416+
• 作为产物：
  描述：

  4-溴苄基亚磷酸二乙酯 在 tris(dibenzylideneacetone)dipalladium (0) sodium hydride 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.33h， 生成 trans-4-(N-methyl-N-phenylamino)stilbene
  参考文献：
  名称：

  Fluorescence Enhancement of trans-4-Aminostilbene by N-Phenyl Substitutions:  The “Amino Conjugation Effect”

  摘要：

  The synthesis, structure, and photochemical behavior of the trans isomers of 4-(N-phenylamino)stilbene (1c), 4-(A methyl-N-phenylamino)stilbene (1d), 4-(NN-diphenylamino)stilbene (le), and 4-(N-(2,6dimethylphenyl)amino)stilbene (1f) are reported and compared to that of 4-aminostilbene (1a) and 4-N,N-dimethylaminostilbene (1b). Results for the corresponding 3-styrylpyridine (2) and 2-styrylnaphthalene analogues (3) are also included. The introduction of N-phenyl substituents to 4-aminostilbenes leads to a more planar ground-state geometry about the nitrogen atom, a red shift of the absorption and fluorescence spectra, and a less distorted structure with a larger charge-transfer character for the fluorescent excited state. Consequently, the N-phenyl derivatives 1c-e have low photoisomerization quantum yields and high fluorescence quantum yields at room temperature, in contrast to the behavior of la, 1b, and most unconstrained monosubstituted trans-stilbenes. The isomerization of 1c and 1d is a singlet-state process, whereas it is a triplet-state process for le, presumably due to a relatively higher singlet-state torsional barrier. The excited-state behavior of 1f resembles 1a and 1b instead of 1c-e as a consequence of the less planar amine geometry and weaker orbital interactions between the N-phenyl and the aminostilbene groups. Such an N-phenyl substituent effect is also found for 2 and 3 and thus appears to be general for stilbenoid systems. The nature of this effect can be described as an ''amino conjugation effect''.

  DOI：

  10.1021/ja016416+

文献信息

• Binaphthalene derivatives, preparation method thereof and organic electronic device using the same
  申请人：Bae Soon Jae

  公开号：US20070108892A1

  公开（公告）日：2007-05-17

  The present invention relates to a new binaphthalene derivative, a preparation method thereof, and an organic electronic device using the same. The binaphthalene derivative according to the present invention can perform functions of hole injection and transportation, electron injection and transportation, or light emission in an organic electronic device including an organic light-emitting device, and the device according to the present invention has excellent characteristics in terms of efficiency, drive voltage and stability, and in particular excellent effects such as a low voltage and a long life time.
• ANTHRACENE DERIVATIVE AND AN ORGANIC ELECTRONIC DEVICE USING THE SAME
  申请人：Jang Hye-Young

  公开号：US20110108826A1

  公开（公告）日：2011-05-12

  The present invention relates to a novel anthracene derivative and an organic electronic device using the same. The anthracene derivative can act as a hole injecting, hole transporting, electron injecting and transporting, or light emitting material in an organic light emitting device and an organic electronic device. In particular, the anthracene derivative can act as a light emitting host. The organic electronic device according to the present invention has excellent characteristics in views of efficiency, the driving voltage, and the stability.
• NEW ANTHRACENE DERIVATIVE AND AN ORGANIC ELECTRONIC DEVICE USING THE SAME
  申请人：Kim Kong-Kyeom

  公开号：US20110114934A1

  公开（公告）日：2011-05-19

  The present invention relates to a novel anthracene derivative and an organic electronic device using the same. The anthracene derivative can act as a hole injecting, hole transporting, electron injecting and transporting, or light emitting material in an organic light emitting device and an organic electronic device. In particular, the anthracene derivative can act as a light emitting host. The organic electronic device according to the present invention has excellent characteristics in views of efficiency, the driving voltage, and the stability.
• BINAPHTHALENE DERIVATIVES, PREPARATION METHOD THEREOF AND ORGANIC ELECTRONIC DEVICE USING THE SAME
  申请人：LG CHEM, LTD.

  公开号：US20140183505A1

  公开（公告）日：2014-07-03

  The present invention relates to a new binaphthalene derivative, a preparation method thereof, and an organic electronic device using the same. The binaphthalene derivative according to the present invention can perform functions of hole injection and transportation, electron injection and transportation, or light emission in an organic electronic device including an organic light-emitting device, and the device according to the present invention has excellent characteristics in terms of efficiency, drive voltage and stability, and in particular excellent effects such as a low voltage and a long life time.
• US8674138B2
  申请人：——

  公开号：US8674138B2

  公开（公告）日：2014-03-18