4-[N,N-bis(2-pyridyl)amino]benzonitrile | 700845-96-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[N,N-bis(2-pyridyl)amino]benzonitrile
• 英文别名: 1-(N,N-bis(2-pyridyl)amino)-4-cyanobenzene；4-[Di(pyridin-2-yl)amino]benzonitrile；4-(dipyridin-2-ylamino)benzonitrile
• CAS: 700845-96-1
• 化学式: C₁₇H₁₂N₄
• 分子量: 272.309
• InChiKey: JDPUAGCFKOSGRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[N,N-bis(2-pyridyl)amino]benzonitrile 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以47%的产率得到4-(di(pyridin-2-yl)amino)benzaldehyde
  参考文献：
  名称：

  Molecular two-photon sensor for metal ions derived from bis(2-pyridyl)amine

  摘要：

  A molecular two-photon sensor for the metal ions derived from bis(2-pyridyl)amine as the receptor is reported. The sensor emits strong two-photon fluorescence when excited by 780 nm laser photons. Moreover, the binding constants measured by the one- and two-photon fluorescence are similar. This result may be useful for the design of efficient two-photon fluorescence probe for biological substrates. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cplett.2005.05.063
• 作为产物：
  描述：

  2-溴吡啶 、 对氨基苯腈 在 1,1'-双(二苯基膦)二茂铁 、 tris(dibenzylideneacetone)dipalladium (0) 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以43%的产率得到4-(pyridin-2-ylamino)benzonitrile
  参考文献：
  名称：

  Zn(II)-Induced Ground-State π-Deconjugation and Excited-State Electron Transfer in N,N-Bis(2-pyridyl)amino-Substituted Arenes

  摘要：

  The synthesis and X-ray crystal structures of two N,N-bis(2-pyridyl)amino (dpa)-substituted aromatic systems (Ar-dpa) 1 (Ar = 4,4'-disubstituted trans-stilbene) and 2 (Ar = 1,4-disubstituted benzene) and their ZnCl2 complexes (1/ZnCl2 and 2/ZnCl2) are reported. The fluoroionophoric behavior of 1-2 in response to Zn(II) in acetonitrile also has been investigated. In addition, compound 3DPA has been prepared and served as a pi-deconjugated model for 1DPA. The observed crystal structures for 1/ZnCl2 and 2/ZnCl2 Could be divided into two distinct types, the planar and the twisted forms, depending on the aryl-dpa (C-ph-NC3) dihedral angle. The twisted form is more favorable for these complexes unless the arene has a strong "push-pull" character. Nonetheless, the degree of pi-conjugation between the N-pyridyl and the N-aryl group is reduced in both complex forms when compared with the free ligands. Such a Zn(II)-induced pi-deconjugation not only directly affects the internal charge transfer (ICT) fluorescence of the dpa-substituted stilbenes but also facilitates the occurrence of photoinduced electron transfer (PET) from the stilbene donor to the dpa/Zn(II) acceptor. The PET process is particularly important in accounting for the observed Zn(II)-induced fluorescence quenching for 1DPA as well as 3DPA.

  DOI：

  10.1021/jo049902z

文献信息

• Zn(II)-Induced Ground-State π-Deconjugation and Excited-State Electron Transfer in <i>N,N</i>-Bis(2-pyridyl)amino-Substituted Arenes
  作者：Jye-Shane Yang、Yan-Duo Lin、Yu-Hsi Lin、Fen-Ling Liao

  DOI：10.1021/jo049902z

  日期：2004.5.1

  The synthesis and X-ray crystal structures of two N,N-bis(2-pyridyl)amino (dpa)-substituted aromatic systems (Ar-dpa) 1 (Ar = 4,4'-disubstituted trans-stilbene) and 2 (Ar = 1,4-disubstituted benzene) and their ZnCl2 complexes (1/ZnCl2 and 2/ZnCl2) are reported. The fluoroionophoric behavior of 1-2 in response to Zn(II) in acetonitrile also has been investigated. In addition, compound 3DPA has been prepared and served as a pi-deconjugated model for 1DPA. The observed crystal structures for 1/ZnCl2 and 2/ZnCl2 Could be divided into two distinct types, the planar and the twisted forms, depending on the aryl-dpa (C-ph-NC3) dihedral angle. The twisted form is more favorable for these complexes unless the arene has a strong "push-pull" character. Nonetheless, the degree of pi-conjugation between the N-pyridyl and the N-aryl group is reduced in both complex forms when compared with the free ligands. Such a Zn(II)-induced pi-deconjugation not only directly affects the internal charge transfer (ICT) fluorescence of the dpa-substituted stilbenes but also facilitates the occurrence of photoinduced electron transfer (PET) from the stilbene donor to the dpa/Zn(II) acceptor. The PET process is particularly important in accounting for the observed Zn(II)-induced fluorescence quenching for 1DPA as well as 3DPA.
• Molecular two-photon sensor for metal ions derived from bis(2-pyridyl)amine
  作者：Hyun Cheol Ahn、Si Kyung Yang、Hwan Myung Kim、Shaojun Li、Seung-Joon Jeon、Bong Rae Cho

  DOI：10.1016/j.cplett.2005.05.063

  日期：2005.7

  A molecular two-photon sensor for the metal ions derived from bis(2-pyridyl)amine as the receptor is reported. The sensor emits strong two-photon fluorescence when excited by 780 nm laser photons. Moreover, the binding constants measured by the one- and two-photon fluorescence are similar. This result may be useful for the design of efficient two-photon fluorescence probe for biological substrates. (c) 2005 Elsevier B.V. All rights reserved.