N-(4-amino-2,5-dimethylphenyl)-4-nitronaphthalene-1,8-dicarboximide | 831227-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(4-amino-2,5-dimethylphenyl)-4-nitronaphthalene-1,8-dicarboximide
• 英文别名: 4-nitro-N-(4-amino-2,5-dimethylphenyl)-1,8-naphthalimide；2-(4-amino-2,5-dimethylphenyl)-6-nitrobenzo[de]isoquinoline-1,3-dione
• CAS: 831227-52-2
• 化学式: C₂₀H₁₅N₃O₄
• 分子量: 361.357
• InChiKey: LDQPCICZOPIJRR-UHFFFAOYSA-N

物化性质

• 沸点：
  669.6±55.0 °C(Predicted)
• 密度：
  1.459±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']bis([1,3]dioxole)-4-yl)phenyl)piperazine 、 N-(4-amino-2,5-dimethylphenyl)-4-nitronaphthalene-1,8-dicarboximide 在 sodium carbonate 、 palladium 10% on activated carbon 、 氢气 作用下， 以 二甲基亚砜 为溶剂， 20.0~70.0 ℃ 、172.37 kPa 条件下， 反应 0.5h， 以410 mg的产率得到2-(4-amino-2,5-dimethylphenyl)-6-(4-(4-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']bis([1,3]dioxole)-4-yl)phenyl)piperazin-1-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Carmieli, Raanan; Mi, Qixi; Ricks, Annie Butler, Journal of the American Chemical Society, 2009, vol. 131, p. 8372 - 8373

  摘要：

  DOI：

文献信息

• Photoinduced Hole Injection into a Self-Assembled π-Extended G-Quadruplex
  作者：Yi-Lin Wu、Kristen E. Brown、Daniel M. Gardner、Scott M. Dyar、Michael R. Wasielewski

  DOI：10.1021/jacs.5b00977

  日期：2015.3.25

  We have prepared a G-quadruplex (GQ:1) that incorporates an 8-(4'-aminophenylethynyl)guanine (GEAn) electron donor covalently attached to a 4-aminonaphthalene-1,8-imide (ANT) chromophore and a naphthalene-1,8:4,5-bis-(dicarboximide) (NDI) electron acceptor (GEAn-ANI-NDI, 1). In the presence of KPF6 in tetrahydrofuran (THE), 1 self-assembles into a monodisperse, C-4-symmetric GQ:1 with small spatial intraquadruplex overlap between the ANI-NDI units. Photoexcitation of monomeric 1 induces the two-step charge transfer GEAn-1*ANI-NDI -> GEAn(+center dot)-ANI(-center dot)-NDI -> GEAn(+center dot)-ANI-NDI-center dot that occurs in tau(CSI) = 5 ps and tau(CS2) = 330 ps, respectively, while charge recombination in ca. 300 ns. Sharpening of the GEAn(+center dot) transient absorption and a shift of the ethynyl vibrational frequency in 1 were observed, concomitant with the stepwise electron transfer from ANI(-center dot) to NDI. Formation of GQ:1 from 1 in THE increases the secondary charge-shifting rate (tau(CS2) = 110 ps) and results in no change in ethynyl vibrational frequency. Charge recombination in GQ:1 is slowed by enhanced radical-pair intersystem crossing driven by the greater number of hyperfine couplings in the assembly. Moreover, time-resolved EPR spectroscopy shows that the spin spin-exchange interaction (J) between the radicals of GEAn(+center dot)-ANI-NDI-center dot within GQ-1 is smaller than that of 1, suggesting that the spin (charge) density in GEAn(+center dot) is more dispersed in GQ-1. The spectroscopic results are consistent with hole sharing among the guanines within the G-quadruplex that is kinetically competitive with the formation of GEAn(+center dot). This suggests that G-quadruplexes can serve as effective hole conduits in ordered donor-acceptor assemblies.