N-octylbenzene-1,2-dicarboxyanhydride-4,5-dicarboximide | 164120-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-octylbenzene-1,2-dicarboxyanhydride-4,5-dicarboximide
• 英文别名: 6-Octylfuro[3,4-f]isoindole-1,3,5,7-tetrone
• CAS: 164120-94-9
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: NOWJGEIWVVEZLY-UHFFFAOYSA-N

物化性质

• 沸点：
  510.0±33.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-octylbenzene-1,2-dicarboxyanhydride-4,5-dicarboximide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 、 calcium oxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.0h， 生成 [5-[(4'-(N-(N'-octyl)pyromellitic diimide)phenyl)ethynyl]-10,20-diphenylporphinato]zinc(II)
  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
• 作为产物：
  描述：

  辛胺 、 均苯四甲酸二酐 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 以1.10 g的产率得到N-octylbenzene-1,2-dicarboxyanhydride-4,5-dicarboximide
  参考文献：
  名称：

  基于均苯四酰亚胺衍生罗丹明的 Spiro 致密电子供体-受体二元组中的长寿命电荷转移状态：电荷转移动力学和电子自旋极化

  摘要：

  通过螺季碳原子连接电子供体和受体，制备了一种新型的全刚性螺电子供体-受体二元组，从而完全抑制了电子供体和受体之间的扭转。该二元组显示出具有高能级（约 2.61 eV）的长寿命3 CT 状态（2.6 μs），CT 状态的电子自旋多重性通过时间分辨 EPR 光谱得到证实。

  DOI：

  10.1002/anie.202203758

文献信息

• Conformational Gating of Long Distance Electron Transfer through Wire-like Bridges in Donor−Bridge−Acceptor Molecules
  作者：William B. Davis、Mark A. Ratner、Michael R. Wasielewski

  DOI：10.1021/ja010330z

  日期：2001.8.1

  influence that bridge dynamics have on electron transfer through these oligomers. The temperature dependence of the charge separation (CS) rates in all five molecules does not appear to obey the predictions of standard ET theories based upon the Condon approximation. All five molecules show behavior consistent with CS being "gated" by torsional motion between the tetracene donor and the first bridge phenyl

  一系列五个供体 - 桥 - 受体（DBA）分子，其中供体是并四苯，受体是均苯四亚胺，桥分子是长度增加的低聚对亚苯基亚乙烯基（OPV）已显示经历电子转移（ET ) 通过两种机制。当桥很短时，强烈依赖于距离的超交换动力学占主导地位，而当桥较长时，桥辅助跳跃动力学占主导地位。后一种机制导致 ET 相对软的距离依赖性，其中 OPV 低聚物有效地充当分子线。我们现在报告关于桥动力学对通过这些低聚物的电子转移的关键影响的研究。所有五个分子中电荷分离 (CS) 速率的温度依赖性似乎不符合基于 Condon 近似的标准 ET 理论的预测。所有五个分子都表现出与 CS 通过并四苯供体和第一个桥苯环之间的扭转运动“门控”一致的行为。这是基于在 5-苯基并四苯中以已知振动模式的频率测量的所有五个分子的 CS 活化能几乎相等。在含有反式二苯乙烯桥的分子中，并四苯-苯基扭转运动与乙烯基和与其相连的苯基之间发生竞争。这导致复杂的温度依赖性
• Influence of Energetics and Electronic Coupling on Through-Bond and Through-Space Electron Transfer within U−Shaped Donor-Bridge-Acceptor Arrays
  作者：Emily A. Weiss、Louise E. Sinks、Aaron S. Lukas、Erin T. Chernick、Mark A. Ratner、Michael R. Wasielewski

  DOI：10.1021/jp037756f

  日期：2004.7.1

  functionalized aromatic imide and diimide donors and acceptors arranged in rodlike linear structures and in U-shaped folded structures on xanthene scaffolds. Femtosecond and nanosecond transient absorption spectroscopy is used to explore the relative efficiency of through-bond and through-space electron transfer in these molecules. The magnitude of the electronic coupling between the oxidized donor and

  我们在这里介绍了供体-桥-受体阵列中的多步电子转移机制，该阵列由功能化的芳香族酰亚胺和二酰亚胺供体和受体组成，这些供体和受体以棒状线性结构和 U 形折叠结构排列在呫吨支架上。飞秒和纳秒瞬态吸收光谱用于探索这些分子中通过键和通过空间电子转移的相对效率。氧化供体和还原受体之间电子耦合的大小通过直接测量自由基离子对内的单重态-三重态分裂 2J 来专门探测，使用磁场对自由基离子对重组产生的三重态产率的影响. 这些数据用于定量评估能量学和电子耦合对电子转移机制的影响。发现当受体减少时，空间电子转移是 U 形结构中的一种可行机制。
• Synthesis of Directly Linked Zinc(II) Porphyrin–Imide Dyads and Energy Gap Dependence of Intramolecular Electron Transfer Reactions
  作者：Naoya Yoshida、Tomoya Ishizuka、Katsuyuki Yofu、Masataka Murakami、Hiroshi Miyasaka、Tadashi Okada、Yasushi Nagata、Akira Itaya、Hyun Sun Cho、Dongho Kim、Atsuhiro Osuka

  DOI：10.1002/chem.200204588

  日期：2003.6.16

  to determine the rates of photoinduced charge separation, 1ZP* - Im --> ZP+ - Im-, and subsequent thermal charge recombination ZP+ - Im- --> ZP - Im. The free-energy gap dependence (energy gap law) has been probed from the normal to the nearly top region for the charge separation rate alone, and only the inverted region for the charge recombination rate. Although both of the energy gap dependencies

  已经制备了一系列的锌（II）卟啉-亚胺二联体（ZP-Im），其中供电子的ZP部分直接与中位的电子接受酰亚胺部分相连，用于检查分子内的能隙依赖性具有大电子耦合的电子转移反应。X射线晶体结构揭示了酰亚胺部分朝向卟啉平面的近乎垂直的构象。电荷分离的能隙1ZP *-Im-> ZP +-Im-通过改变电子接受酰亚胺部分以覆盖DMF中约0.8 eV的范围而变化。通过皮秒-飞秒瞬态吸收研究，已在三种溶剂（甲苯，THF和DMF）中获得了确定的电子转移证据，这使我们能够确定光致电荷分离的速率，1ZP *-Im-> ZP +-Im-，然后进行热电荷重组ZP +-Im--> ZP-Im。仅从电荷分离速率的正态到接近顶部的自由能隙依赖关系（能量隙定律）就被探究了，对于电荷复合率，仅从倒置的区域进行了探究。尽管两个能隙依赖性都可以通过简化的半经典方程近似地再现，但是当我们考虑用一种平均频率模式代替高频振动的影响时，
• Reversibly Thermochromic Compositions
  申请人：Fischer Walter

  公开号：US20090302284A1

  公开（公告）日：2009-12-10

  The present invention pertains to a reversibly thermochromic system comprising a substituted or an unsubstituted 6,11-dihydroxy-naphthacene-5,12-dione and a base and to a reversibly thermochromic composition comprising the reversibly thermochromic system and a carrier material and to novel substituted 6,11-dihydroxy-naphthacene-5,12-diones.

  本发明涉及一种可逆热致变色系统，包括取代或未取代的6,11-二羟基萘并[5,12-二酮]和一种碱，以及一种可逆热致变色组合物，包括可逆热致变色系统和载体材料，还涉及新型的取代的6,11-二羟基萘并[5,12-二酮]。
• Femtosecond Transient Grating Studies of Chlorophylls and a Chlorophyll-Based Electron Donor-Acceptor Molecule
  作者：Gary P. Wiederrecht、Walter A. Svec、Mark P. Niemczyk、Michael R. Wasielewski

  DOI：10.1021/j100021a069

  日期：1995.5

  Ultrafast, polarization selective, transient grating studies are performed on several chlorophylls and an electron donor-acceptor molecule, Zn DMPPH-PI, that consists of a zinc methyl 13(1)-desoxopyropheophorbide a donor covalently linked to a pyromellitimide acceptor. The covalent linkage between the donor and acceptor constrains the distance and geometric relationship between them. The ability of the experiment to determine the nature of a particular physical phenomenon through separable polarization characteristics of the diffracted signal is used to analyze photophysical and photochemical processes in these molecules. This is achieved for cases in which the observed physical processes have overlapping spectral contributions, a situation where linear dichroism experiments are very difficult to interpret. Careful analysis of the absorption grating data allows us to determine rotational anisotropy values for the molecules in solution, two-photon absorption-state symmetries, and the relative orientation of the donor and acceptor in the Zn DMPPH-PI molecule. These results demonstrate complete separation of the contributions to the time dependent diffracted signal from the two radical ion pair products formed in the electron transfer reaction.