1,7-(3',5'-di-t-butylphenoxy)perylene-3,4:9,10-tetracarboxyanhydride | 404871-21-2

• 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: 1,7-(3',5'-di-t-butylphenoxy)perylene-3,4:9,10-tetracarboxyanhydride
• 英文别名: 1,7-(3',5'-di-t-butylphenoxy)perylene-3,4-dicarboxyanhydride；1,7-bis(3'5'-di-tert-butylphenoxy)perylene-3,4:9,10-tetracarboxydianhydride；1,7-(3',5'-di-tert-butylphenoxy)perylene-3,4:9,10-tetracarboxydianhydride；1,7-bis(3,5-di-tert-butylphenoxy)perylene-3,4:9,10-tetracarboxylic dianhydride；1,7-(3’,5‘-di-t-butylphenoxy)perylene-3,4:9,10-tetracarboxydianhydride；1,7-(3',5'-di-t-butylphenoxy)perylene-3,4:9,10-tetracarboxydianhydride；11,22-Bis(3,5-ditert-butylphenoxy)-7,18-dioxaheptacyclo[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: 404871-21-2
• 化学式: C₅₂H₄₈O₈
• 分子量: 800.948
• InChiKey: FEMQUQIIMLTPTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.2
• 重原子数：
  60
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-氨基吡啶 、 1,7-(3',5'-di-t-butylphenoxy)perylene-3,4:9,10-tetracarboxyanhydride 在 zinc diacetate 作用下， 以 喹啉 为溶剂， 反应 24.0h， 以75%的产率得到N,N'-di(4-pyridyl)-1,7-bis(3',5'-di-tert-butylphenoxy)perylene-3,4:9,10-tetracarboxylic acid bisimide
  参考文献：
  名称：

  Supramolecular Bis(rutheniumphthalocyanine)−Perylenediimide Ensembles:  Simple Complexation as a Powerful Tool toward Long-Lived Radical Ion Pair States

  摘要：

  A novel supramolecular electron donor-acceptor hybrid (1) has been designed through axial coordination of a perylenebisimide moiety [BPyPDI], bearing two 4-pyridyl substituents at the imido positions, to the ruthenium(II) metal centers of two phthalocyanines [Ru(CO)Pc]. This modular protocol enables access to electron donor-acceptor hybrids with potentially great design flexibility. The new array ( 1) has been characterized by standard spectroscopic methods, and its photophysical behavior has been established by using ultrafast and fast time-resolved techniques. Photoexcitation of either chromophore leads to a product that is essentially identical for both pathways, that is, evolving from the [Ru(CO) Pc] or [BPyPDI] singlet excited state. Features of the photoproduct are new transient maxima at 530 and 725 nm, plus transient minima at 580 nm and 650 nm. Based on the radiolytically generated [BPyPDI.-](i.e., one-electron reduction of [BPyPDI]) and [Ru(CO)Pc-.+] (i.e., one-electron oxidation of [Ru(CO)Pc]) features, which in the 300 and 900 nm range remarkably resemble those noted for photoexcited 1, we attribute the photolytically generated species to the composite spectrum of the [Ru(CO)Pc.+-BPyPDI.--RuCOPc] radical ion pair state. Its lifetime, which is on the order of 115 +/- 5 ns, reveals a significant stabilization and confirms that the strongly exothermic charge recombination dynamics are placed deeply in the inverted region of the Marcus parabola.

  DOI：

  10.1021/ja0622195
• 作为产物：
  描述：

  3,4,9,10-苝四羧酸二酐 在 硫酸 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 57.0h， 生成 1,7-(3',5'-di-t-butylphenoxy)perylene-3,4:9,10-tetracarboxyanhydride
  参考文献：
  名称：

  来自共价多发色团苝-3,4:9,10-双（二甲酰亚胺）结构单元的超分子光捕获阵列的自组装

  摘要：

  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

  DOI：

  10.1021/ja039820c

文献信息

• [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。
• Hydrogen-Bonded Oligo(p-phenylenevinylene) Functionalized with Perylene Bisimide: Self-Assembly and Energy Transfer
  作者：Jian Zhang、Freek J. M. Hoeben、Maarten J. Pouderoijen、Albertus P. H. J. Schenning、E. W. Meijer、Frans C. De Schryver、Steven De Feyter

  DOI：10.1002/chem.200600651

  日期：2006.12.4

  different electronic properties of the oligo(p-phenylenevinylene) and perylene bisimide moieties. In dodecane, the molecule self-assembles into H-type aggregates that are still soluble as a result of the hydrophobic shell formed by the dodecyloxy wedges. The donor-acceptor molecule is characterized by efficient energy transfer from the photoexcited OPV to the perylene bisimide. Mixed assemblies with analogous

  我们描述了合成，超分子在表面和溶液中的有序排列，以及OPV4UT-PERY（具有共价连接的bi双酰亚胺部分的低聚（对亚苯基亚乙烯基）（OPV））的光物理特征。在氯仿中，分子通过脲基-s-三嗪阵列的四重氢键形成二聚体。这通过扫描隧道显微镜（STM）研究得到支持，该研究揭示了在液体（1,2,4-三氯苯）/固体（石墨）界面处的二聚体形成。此外，依赖于偏压的STM成像中的对比度反转提供了有关低聚（对亚苯基亚乙烯基）和per双酰亚胺部分的有序性和不同电子性质的信息。在十二烷中，由于十二烷氧基楔形分子形成的疏水壳，分子自组装成H型聚集体，这些聚集体仍然可溶。供体-受体分子的特征在于从光激发的OPV到to二酰亚胺的有效能量转移。已经在十二烷溶液中制备了具有类似OPV的，缺少per双酰亚胺单元的混合组件，并且已经通过荧光光谱研究了向结合的per双酰亚胺的能量转移。
• 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。
• Making a Molecular Wire:  Charge and Spin Transport through <i>p</i><i>ara</i>-Phenylene Oligomers
  作者：Emily A. Weiss、Michael J. Ahrens、Louise E. Sinks、Alexey V. Gusev、Mark A. Ratner、Michael R. Wasielewski

  DOI：10.1021/ja0398215

  日期：2004.5.1

  Functional molecular wires are essential for the development of molecular electronics. Charge transport through molecules occurs primarily by means of two mechanisms, coherent superexchange and incoherent charge hopping. Rates of charge transport through molecules in which superexchange dominates decrease approximately exponentially with distance, which precludes using these molecules as effective molecular wires. In contrast, charge transport rates through molecules in which incoherent charge hopping prevails should display nearly distance independent, wirelike behavior. We are now able to determine how each mechanism contributes to the overall charge transport characteristics of a donor-bridge-acceptor (D-B-A) system, where D = phenothiazine (PTZ), B = p-oligophenylene, and A = perylene-3,4:9,10-bis(dicarboximide) (PDI), by measuring the interaction between two unpaired spins within the system's charge separated state via magnetic field effects on the yield of radical pair and triplet recombination product.