N-(2-ethylhexyl)-1,7-(3',5'-di-t-butylphenoxy)perylene-3,4-dicarboxyanhydride-9,10-dicarboximide | 457892-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: N-(2-ethylhexyl)-1,7-(3',5'-di-t-butylphenoxy)perylene-3,4-dicarboxyanhydride-9,10-dicarboximide
• 英文别名: 11,22-Bis(3,5-ditert-butylphenoxy)-18-(2-ethylhexyl)-7-oxa-18-azaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2,4,9,11,13(23),14,16(24),20,25-decaene-6,8,17,19-tetrone
• CAS: 457892-77-2
• 化学式: C₆₀H₆₅NO₇
• 分子量: 912.179
• InChiKey: MVHOXCAIRSYLDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17
• 重原子数：
  68
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  99.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,N-二乙基对苯二胺 、 N-(2-ethylhexyl)-1,7-(3',5'-di-t-butylphenoxy)perylene-3,4-dicarboxyanhydride-9,10-dicarboximide 在 吡啶 作用下， 反应 24.0h， 以74%的产率得到11,22-Bis(3,5-ditert-butylphenoxy)-7-[4-(diethylamino)phenyl]-18-(2-ethylhexyl)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2,4,9,11,13(23),14,16(24),20,25-decaene-6,8,17,19-tetrone
  参考文献：
  名称：

  Photoinduced Electron Transfer in Self-Assembled Dimers of 3-Fold Symmetric Donor−Acceptor Molecules Based on Perylene-3,4:9,10-bis(dicarboximide)

  摘要：

  The influence of pi-stacking on photoinduced electron transfer in a series of donor-acceptor molecules attached to a 3-fold symmetric scaffold was studied. The donor-acceptor unit is a DEA-PDI pair (DEA = N,N-diethylaniline; PDI = perylene-3,4:9,10-bis(dicarboximide)), in which the 4-position of DEA is covalently attached to the nitrogen atom of one imide of PDI. One, two, or three DEA-PDI units are attached to the para position of one of the phenyl groups of 1,3,5-triphenylbenzene, using the other PDI imide group to form mono-, his-, and tris(DEA-PDI). These molecules demonstrate an increasing tendency to self-assemble into pi-stacked dimers in solution in the order mono(DEA-PDI) much less than bis(DEA-PDI) < tris(DEA-PDI). Photoinduced electron transfer in both the monomers and self-assembled dimers was studied by femtosecond transient absorption spectroscopy. The charge separation (CS) and charge recombination time (CR) constants are found to be independent of pi-stacking aptitudes, while the transient spectral features differ significantly upon dimerization. The electronic interactions imposed by pi-stacking appear to change the energies of the ground, excited, and ionic states of DEA-PDI to a similar extent, which results in similar energies for CS and CR within the monomers and dimers.

  DOI：

  10.1021/jp048883u
• 作为产物：
  描述：

  2-乙基己胺 在 咪唑 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 74.0h， 以24%的产率得到N-(2-ethylhexyl)-1,7-(3',5'-di-t-butylphenoxy)perylene-3,4-dicarboxyanhydride-9,10-dicarboximide
  参考文献：
  名称：

  WO2008/38047

  摘要：

  公开号：

文献信息

• Self-Assembly of Supramolecular Light-Harvesting Arrays from Covalent Multi-Chromophore Perylene-3,4:9,10-bis(dicarboximide) Building Blocks
  作者：Michael J. Ahrens、Louise E. Sinks、Boris Rybtchinski、Wenhao Liu、Brooks A. Jones、Jovan M. Giaimo、Alexy V. Gusev、Andrew J. Goshe、David M. Tiede、Michael R. Wasielewski

  DOI：10.1021/ja039820c

  日期：2004.7.1

  We report on two multi-chromophore building blocks that self-assemble in solution and on surfaces into supramolecular light-harvesting arrays. Each building block is based on perylene-3,4:9,10-bis(dicarboximide) (PDI) chromophores. In one building block, N-phenyl PDI chromophores are attached at their para positions to both nitrogens and the 3 and 6 carbons of pyromellitimide to form a cross-shaped

  我们报告了两个多发色团构建块，它们在溶液中和表面上自组装成超分子光捕获阵列。每个构建块都基于苝-3,4:9,10-双（二甲酰亚胺）（PDI）发色团。在一个构建模块中，N-苯基 PDI 发色团在其对位连接到氮和均苯四甲酰亚胺的 3 和 6 个碳原子，形成一个十字形分子 (PI-PDI(4))。在第二个构件中，N-苯基 PDI 发色团在其对位连接到第五个 PDI 的氮和 1 和 7 个碳原子，以产生鞍形分子 (PDI(5))。这些分子在甲苯和 2-甲基四氢呋喃溶液中自组装成部分有序的二聚体结构 (PI-PDI(4))(2) 和 (PDI(5))(2)，其中 PDI 分子彼此大致平行，主要是由于相邻 PDI 生色团之间的 PI-PI 相互作用。在疏水表面上，PDI(5) 长成平均长度为 130 nm 的棒状纳米结构，如原子力显微镜所示。这些超分子二聚体在溶液中的光激发直接证明了激发的 PDI 生色团与附近其他
• [EN] ENERGY STORAGE MOLECULAR MATERIAL, CRYSTAL DIELECTRIC LAYER AND CAPACITOR<br/>[FR] MATIÈRE MOLÉCULAIRE DE STOCKAGE D'ÉNERGIE, COUCHE DIÉLECTRIQUE DE CRISTAL ET CONDENSATEUR
  申请人：CAPACITOR SCIENCES INC

  公开号：WO2016187584A1

  公开（公告）日：2016-11-24

  The present disclosure provides an energy storage molecular material, crystal dielectric layer and capacitor which may solve a problem of the further increase of volumetric and mass density of reserved energy associated with some energy storage devices, and at the same time reduce cost of materials.

  本公开提供了一种能量存储分子材料、晶体介质层和电容器，可以解决一些能量存储设备所关联的储能体积和质量密度进一步增加的问题，并同时降低材料成本。
• Charge Transport in Photofunctional Nanoparticles Self-Assembled from Zinc 5,10,15,20-Tetrakis(perylenediimide)porphyrin Building Blocks
  作者：Tamar van der Boom、Ryan T. Hayes、Yongyu Zhao、Patrick J. Bushard、Emily A. Weiss、Michael R. Wasielewski

  DOI：10.1021/ja026286k

  日期：2002.8.1

  nanoparticles results in quantitative charge separation in 3.2 ps to form ZnTPP(+)PDI(-) radical ion pairs, in which the radical anion rapidly migrates to PDI molecules that are, on average, 21 A away, as evidenced by magnetic field effects on the yield of the PDI triplet state that results from radical ion pair recombination. These nanoparticles exhibit charge transport properties that combine important

  设计用于进行光化学能量转换的分子通常采用几个连续的电子转移，光合蛋白质也是如此。然而，这些分子通常无法实现半导体器件的广泛电荷传输特性。我们制备了一个大分子，其中四个既收集光子又接受电子的苝-3,4:9,10-四羧基二亚胺 (PDI) 分子连接到中央锌 5,10,15,20-四苯基卟啉 (ZnTPP) 电子捐赠者。在 PDI 分子的范德华堆积驱动下，该分子在溶液和固态中自组装成有序的纳米粒子。纳米粒子的光激发导致在 3.2 ps 内定量电荷分离以形成 ZnTPP(+)PDI(-) 自由基离子对，其中自由基阴离子迅速迁移到 PDI 分子中，平均而言，距离为 21 A，正如磁场对自由基离子对重组导致的 PDI 三重态产率的影响所证明的那样。这些纳米粒子表现出电荷传输特性，结合了光合作用和半导体光转换系统的重要特征。
• Electron Hopping in π-Stacked Covalent and Self-Assembled Perylene Diimides Observed by ENDOR Spectroscopy
  作者：Michael J. Tauber、Richard F. Kelley、Jovan M. Giaimo、Boris Rybtchinski、Michael R. Wasielewski

  DOI：10.1021/ja057031k

  日期：2006.2.1

  solution-phase electron paramagnetic resonance and electron-nuclear double resonance studies on a series of radical anions based upon perylene-3,4:9,10-bis(dicarboximide) (PDI). The following systems were studied: two PDI monomers, a covalent, cofacial dimer, and two covalent trefoil-PDI3 molecules, one of which self-assembles into pi-stacked dimers. Full sharing of the unpaired electron in the covalent

  我们对一系列基于苝-3,4:9,10-双(二甲酰亚胺) (PDI) 的自由基阴离子进行了室温、溶液相电子顺磁共振和电子核双共振研究。研究了以下系统：两个 PDI 单体、一个共价共面二聚体和两个共价三叶形 PDI3 分子，其中一个自组装成 pi 堆积的二聚体。共价和自组装二聚体中未配对电子的完全共享是通过这些物种中超精细耦合常数相对于单体的减半来揭示的。这些结果和电子吸收光谱表明，在 >107 Hz 时间尺度上的电子跳跃发生在还原和中性发色团对之间。
• Synthesis and dark state EPR properties of PDI‐trityl dyads and triads
  作者：Kevin Kopp、Lars Westhofen、Tobias Hett、Merlin Felix Schwering‐Sohnrey、Maximilian Mayländer、Sabine Richert、Olav Schiemann

  DOI：10.1002/chem.202303635

  日期：2024.2.26

  Covalently‐linked chromophore‐radical systems with their unique optical and magnetic properties are useful for applications in, e. g., quantum information science. To expand the catalog of molecular systems, we synthesized and characterized six novel chromophore–radical and radical‐chromophore‐radical systems employing derivatives of perylene diimide (PDI) as the chromophore and trityl as the radical. The EPR properties of these compounds were evaluated in solution at cryogenic and room temperatures. In addition, the electron spin‐spin coupling in the two bistrityl systems was investigated using DQC measurements. The presented results serve as a basis for further spectroscopic investigations under photoexcitation of the PDI core.

  摘要共价连接的发色团-自由基体系具有独特的光学和磁学特性，可用于量子信息科学等领域。为了扩大分子体系的范围，我们合成并表征了六种新型的发色团-自由基体系和自由基-发色团-自由基体系。在低温和室温溶液中对这些化合物的 EPR 特性进行了评估。此外，还使用 DQC 测量方法研究了两个双三苯甲基体系中的电子自旋-自旋耦合。这些结果为进一步研究 PDI 内核在光激发下的光谱特性奠定了基础。