N-octyl-N'-(4'-iodophenyl)naphthalene-1,4,5,8-tetracarboxylic acid bisimide | 926643-75-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-octyl-N'-(4'-iodophenyl)naphthalene-1,4,5,8-tetracarboxylic acid bisimide
• 英文别名: 4-iodoaniline
• CAS: 926643-75-6
• 化学式: C₂₈H₂₅IN₂O₄
• 分子量: 580.422
• InChiKey: QLKOXAVJHNKSHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  74.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-octyl-N'-(4'-iodophenyl)naphthalene-1,4,5,8-tetracarboxylic acid bisimide 在 palladium dichloride copper diacetate 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 三乙胺 为溶剂， 反应 16.0h， 生成 N-octyl-N'-(4'-ethynylphenyl)naphthalene-1,4,5,8-tetracarboxylic acid bisimide
  参考文献：
  名称：

  Very large acceleration of the photoinduced electron transfer in a Ru(bpy)₃–naphthalene bisimide dyad bridged on the naphthyl core

  摘要：

  通过将萘二酰亚胺（NBI）单元连接到萘基核心上的[Ru(bpy)3]2+，与传统的氮原子连接方式相比，光诱导的铑到NBI的电子转移速率提高了1000倍。

  DOI：

  10.1039/b615085c
• 作为产物：
  描述：

  辛胺 在 calcium oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 N-octyl-N'-(4'-iodophenyl)naphthalene-1,4,5,8-tetracarboxylic acid bisimide
  参考文献：
  名称：

  Synthesis, Electronic Structure, and Electron Transfer Dynamics of (Aryl)ethynyl-Bridged Donor−Acceptor Systems

  摘要：

  The ET dynamics of a series of donor-spacer-acceptor (D-Sp-A) systems featuring (porphinato)zinc(II), (aryl)ethynyl bridge, and arene diimide units were investigated by pump-probe transient absorption spectroscopy. Analysis of these data within the context of the Marcus-Levich-Jortner equation suggests that the pi-conjugated (aryl)ethynyl bridge plays an active role in the charge recombination (CR) reactions of these species by augmenting the extent of (porphinato)zinc(II) cation radical electronic delocalization; this increase in cation radical size decreases the reorganization energy associated with the CR reaction and thereby attenuates the extent to which the magnitudes of the CR rate constants are solvent dependent. The symmetries of porphyrin-localized HOMO and HOMO-1, the energy gap between these two orbitals, and D-A distance appear to play key roles in determining whether the (aryl)ethynyl bridge simply mediates electronic superexchange or functions as an integral component of the D and A units.

  DOI：

  10.1021/ja021278p

文献信息

• Excitation-Wavelength-Dependent Photoinduced Electron Transfer in a π-Conjugated Diblock Oligomer
  作者：Austin L. Jones、Junlin Jiang、Kirk S. Schanze

  DOI：10.1021/jacs.0c03678

  日期：2020.7.22

  the PE bridge unit in oligomers featuring zero and two PE units (T4NDI and T4PE2NDI). The rate of charge recombination decreases from 1.2 x 1011 to 1.0 x 109 s-1 with increasing bridge length between the T4 and NDI components (T4NDI to T4PE4NDI). Furthermore, there wavelength dependent photoinduced electron transfer was not observed in either T4NDI or T4PE2NDI due to insufficient PEn bridge length

  演示了通过选择性激发具有四噻吩 (T4) 和四(亚苯基乙炔) (PE4) 供体块的 π 共轭二嵌段低聚体系统来控制光致电子转移，该供体块用萘二亚胺 (NDI) 受体 (T4PE4NDI) 封盖。每个 π 共轭寡聚链段都有自己的离散电离电位、电子亲和性和光学带隙，这提供了具有特定波长的吸收曲线，可选择性激发 PE4 和 T4 块。因此，当在 370 nm 激发时，T4PE4NDI 可以通过从 PE4 段到 NDI 的超快光致电子转移被选择性激发以形成电荷分离态，但在 420 nm (T4) 激发时不会产生电荷分离态。使用皮秒瞬态吸收技术来探测激发态动力学，揭示了在 370 nm 激发时从 PE4 段到 NDI 发生的超快电荷分离（~4 ps），然后是 T4 段上的阳离子离域。相反，在较长波长 (≥ 420 nm) 的激发下，电子转移受到抑制，其中光谱由 T4 单元主导。研究了电子转移和电荷复合的速率与具有零个和两个
• Photoinduced electron transfer in ruthenium(ii) trisbipyridine complexes connected to a naphthalenebisimidevia an oligo(phenyleneethynylene) spacer
  作者：Frédérique Chaignon、Fabien Buchet、Errol Blart、Magnus Falkenström、Leif Hammarström、Fabrice Odobel

  DOI：10.1039/b810856k

  日期：——

  by electron transfer to form the charge-separated state RuIII–NBI−. This state could not be observed, presumably because the subsequent recombination to the ground state was much faster than its formation. In the dyad linked in 5 position with only one phenyleneethynylene unit, at room temperature, the 3MLCT* state is in equilibrium with the 3NBI* state, and it also decays via electron transfer. The

  三种新的二联体的制备和表征。 三联吡啶钌 复杂的链接到 萘据报道通过不同长度的亚苯基亚乙炔间隔基的双酰亚胺电子受体（一个或两个单元）。二元组的不同之处还在于垫片在锚固环上的锚固位置。联吡啶，附加在4位或5位。循环伏安法和UV-Vis吸收光谱表明，在5-位连接的间隔基确保了更长的π-共轭长度，但电子传递速率表明其电子耦合性低于4-位。光诱导的发射率表明该分子的MLCT激发态显着淬灭。钌在这些二元复合体中。除了与一个亚苯基亚乙炔基单元在5位相连的二元组之外，所有其他二元组的瞬态吸收光谱表明，MLCT激发态几乎完全通过电子转移而衰减，从而形成电荷分离态茹三世–国家情报局-。无法观察到该状态，大概是因为随后重组为基态比其形成快得多。在仅与一个亚苯基亚乙炔基单元连接的5位二元体中，室温下3 MLCT *状态与3 NBI *状态处于平衡状态，并且还会通过电子转移而衰减。这些二重体的显着特征是首先通过锚
• State-Selective Electron Transfer in an Unsymmetric Acceptor−Zn(II)porphyrin−Acceptor Triad: Toward a Controlled Directionality of Electron Transfer from the Porphyrin S₂ and S₁ States as a Basis for a Molecular Switch
  作者：Staffan Wallin、Cyrille Monnereau、Errol Blart、Jean-Richard Gankou、Fabrice Odobel、Leif Hammarström

  DOI：10.1021/jp907824d

  日期：2010.2.4

  A series of Zn(II) porphyrin (ZnP) compounds covalently linked to different electron acceptor units, naphthaleneimide (NI) and naphthalenedimide (NDI), are reported. The aim was to demonstrate a state-selective direction of electron transfer, where excitation to the lowest excited S-1 state of the porphyrin (Q-band excitation) would give electron transfer to the NDI unit, while excitation to the higher S-2 state (Soret-hand excitation) would give electron transfer to the NI unit. This would constitute a basis for an opto-electronic Switch in which the direction of electron transfer and the resulting dipole moment can be controlled by using light input of different color. Indeed, electron transfer from the S-1 state to NDI Occurred in solvents of both high and low polarity, whereas no electron transfer to NDI was observed from the S-2 state. With NI as acceptor instead, very rapid (tau = 200-400 fs) electron transfer from the S-2 state occurred in all solvents. This was followed by an ultrafast (tau approximate to 100 fs) recombination to Populate the porphyrin S-1 state in nearly quantitative yield. The charge-separated state ZnP+NI- was spectroscopically observed, and evidence was obtained that recombination Occurred from a vibrationally excited ("hot") ZnP+NI- state in the more polar solvents. In these solvents, the thermally relaxed ZnP+NI- state lies at lower energy than the S-1 state so that further charge separation occurred from S-1 to form ZnP+NI-. This resulted in a highly unusual "ping-pong" sequence where the reaction went back and forth between locally excited ZnP states and charge-separated states: S-2 double right arrow ZnP+NI"hot"- double right arrow S-1 double right arrow ZnP+NI- double right arrow S-0. The electron transfer dynamics and its solvent dependence are discussed, as well as the function of the present Molecules as molecular switches.