N-(3,5-Diaminophenyl)-4-(N-piperidyl)naphthalene-1,8-dicarboximide | 259656-12-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N-(3,5-Diaminophenyl)-4-(N-piperidyl)naphthalene-1,8-dicarboximide
• CAS: 259656-12-7
• 化学式: C₂₃H₂₂N₄O₂
• 分子量: 386.453
• InChiKey: DHRUMUCTSXEUQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  92.66
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(3,5-Diaminophenyl)-4-(N-piperidyl)naphthalene-1,8-dicarboximide 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 6-[3-(1,3-Dioxo-6-piperidin-1-ylbenzo[de]isoquinolin-2-yl)-5-[2-(13-octyl-5,7,12,14-tetraoxo-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaen-6-yl)-1,3,5,7-tetraoxopyrrolo[3,4-f]isoindol-6-yl]phenyl]-13-octyl-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
  参考文献：
  名称：

  Femtosecond Optical Switching of Electron Transport Direction in Branched Donor−Acceptor Arrays

  摘要：

  The branched donor-acceptor triad 4 and tetrad 5 were synthesized to study the possibility of controlling the direction of electron transfer in a divergent array of electron accepters using ultrafast laser pulses. Compounds 4 and 5 employ 1,3,5-triaminobenzene as the central branch point. In 4, a 4-(N-piperidinyl)-1,8-naphthaleneimide electron donor (ANI) was attached to the 1 position and two electron accepters, 1,8:4, 5-naphthalenediimide, NI, and pyromellitimide, PI, were attached to the 3 and 5 positions of the central benzene ring. In 5, the terminal end of the PI acceptor is functionalized with an additional NI molecule. Selective excitation of ANI in 4 and 5 with 400 nm, 130 fs laser pulses results in exclusive formation of NI--ANI(+)-PI and NI--ANI(+)-PI-NI, respectively. with tau = 115 ps, and a quantum yield of 0.99. Excitation of NI- with 480 nm, 130 fs laser pulses produces the excited doublet state *NI-, which transfers an electron to PI on the second branch of the benzene ring with a time constant of tau = 600 fs in 4 and tau = 750 fs in 5. The overall quantum yields for the two step process are 0.44 and 0.36 in 4 and 5, respectively. The resultant state NI-ANL(+)-PI--NI in 4 undergoes a charge shift reaction returning to the initial ion pair state NI--ANI(+)-PI with tau = 400 ps, while the corresponding state NI-ANI(+)-PI--NI in 5 undergoes a charge shift with tau = 200 ps to yield NI-ANI(+)-PI-NI-, which in turn exhibits a 2000 ps lifetime. These results show that once the electron has been switched to the branch containing the thermodynamically uphill PI acceptor, the electron will cascade down that branch to other accepters that are more easily reduced. Model compounds 1-3, which were synthesized to aid in characterization of the switching dynamics, are also discussed. Photochemical control of directional charge transport may make it possible to design networks of organic molecules for information processing.

  DOI：

  10.1021/jp993774e
• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 以 N-甲基吡咯烷酮 、 乙醇 为溶剂， 反应 7.5h， 生成 N-(3,5-Diaminophenyl)-4-(N-piperidyl)naphthalene-1,8-dicarboximide
  参考文献：
  名称：

  Femtosecond Optical Switching of Electron Transport Direction in Branched Donor−Acceptor Arrays

  摘要：

  The branched donor-acceptor triad 4 and tetrad 5 were synthesized to study the possibility of controlling the direction of electron transfer in a divergent array of electron accepters using ultrafast laser pulses. Compounds 4 and 5 employ 1,3,5-triaminobenzene as the central branch point. In 4, a 4-(N-piperidinyl)-1,8-naphthaleneimide electron donor (ANI) was attached to the 1 position and two electron accepters, 1,8:4, 5-naphthalenediimide, NI, and pyromellitimide, PI, were attached to the 3 and 5 positions of the central benzene ring. In 5, the terminal end of the PI acceptor is functionalized with an additional NI molecule. Selective excitation of ANI in 4 and 5 with 400 nm, 130 fs laser pulses results in exclusive formation of NI--ANI(+)-PI and NI--ANI(+)-PI-NI, respectively. with tau = 115 ps, and a quantum yield of 0.99. Excitation of NI- with 480 nm, 130 fs laser pulses produces the excited doublet state *NI-, which transfers an electron to PI on the second branch of the benzene ring with a time constant of tau = 600 fs in 4 and tau = 750 fs in 5. The overall quantum yields for the two step process are 0.44 and 0.36 in 4 and 5, respectively. The resultant state NI-ANL(+)-PI--NI in 4 undergoes a charge shift reaction returning to the initial ion pair state NI--ANI(+)-PI with tau = 400 ps, while the corresponding state NI-ANI(+)-PI--NI in 5 undergoes a charge shift with tau = 200 ps to yield NI-ANI(+)-PI-NI-, which in turn exhibits a 2000 ps lifetime. These results show that once the electron has been switched to the branch containing the thermodynamically uphill PI acceptor, the electron will cascade down that branch to other accepters that are more easily reduced. Model compounds 1-3, which were synthesized to aid in characterization of the switching dynamics, are also discussed. Photochemical control of directional charge transport may make it possible to design networks of organic molecules for information processing.

  DOI：

  10.1021/jp993774e