5-(2,4-Dioxo-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaen-8-yl)-16-[2,6-di(propan-2-yl)phenyl]-16-azahexacyclo[12.6.2.12,6.011,21.018,22.010,23]tricosa-1(20),2,4,6,8,10(23),11(21),12,14(22),18-decaene-15,17-dione | 187536-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(2,4-Dioxo-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaen-8-yl)-16-[2,6-di(propan-2-yl)phenyl]-16-azahexacyclo[12.6.2.12,6.011,21.018,22.010,23]tricosa-1(20),2,4,6,8,10(23),11(21),12,14(22),18-decaene-15,17-dione
• 英文别名: 5-(2,4-dioxo-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaen-8-yl)-16-[2,6-di(propan-2-yl)phenyl]-16-azahexacyclo[12.6.2.12,6.011,21.018,22.010,23]tricosa-1(20),2,4,6,8,10(23),11(21),12,14(22),18-decaene-15,17-dione
• CAS: 187536-84-1
• 化学式: C₄₆H₃₁NO₅
• 分子量: 677.756
• InChiKey: RTOZIUFBDLLMMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  52
• 可旋转键数：
  4
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  3-氨基戊二酸 、 5-(2,4-Dioxo-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaen-8-yl)-16-[2,6-di(propan-2-yl)phenyl]-16-azahexacyclo[12.6.2.12,6.011,21.018,22.010,23]tricosa-1(20),2,4,6,8,10(23),11(21),12,14(22),18-decaene-15,17-dione 在 zinc diacetate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 16.0h， 生成 3-(6-(2-(2,6-diisopropylphenyl)-1,3-dioxo-2,3-dihydro-1H-benzo[10,5]anthra[2,1,9-def]isoquinolin-8-yl)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)pentanedioic acid
  参考文献：
  名称：

  A Simple and Versatile Route to Stable Quantum Dot−Dye Hybrids in Nonaqueous and Aqueous Solutions

  摘要：

  Hybrid systems consisting of core/shell semiconductor quantum dots (QDs) and organic rylene dyes have been prepared and characterized. Complex formation is mediated by bidentate carboxylate moieties covalently linked to the dye molecules. The complexes were very stable with respect to time (at least months), dilution (sub nM), and precipitation. After preparation in organic solvent, complexes could be easily transferred into water. The strong quenching of QD emission by the dye molecules (transfer efficiencies up to 95%) was satisfactorily modeled by an FRET process. Single complexes immobilized in thin polymer films were imaged by confocal fluorescence microscopy.

  DOI：

  10.1021/ja8073962
• 作为产物：
  描述：

  N-(2,6-diisopropylphen-yl)-9-bromo-perylene-3,4-dicarboximide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四(三苯基膦)钯 、 potassium acetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 反应 32.0h， 生成 5-(2,4-Dioxo-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaen-8-yl)-16-[2,6-di(propan-2-yl)phenyl]-16-azahexacyclo[12.6.2.12,6.011,21.018,22.010,23]tricosa-1(20),2,4,6,8,10(23),11(21),12,14(22),18-decaene-15,17-dione
  参考文献：
  名称：

  合成的由–和Per二酰亚胺组成的受体-供体-受体多发色团用于多步能量转移研究

  摘要：

  基于2010年在包含三甲苯二酰亚胺（TDI）和per二酰亚胺（PDI）的线性多发色团中单重态-单态an灭研究的结果，我们报告了成功合成TDI-PDI-TDI二聚体的详细过程。描述了无效的合成途径，这对于理解复杂的多色团的逐步构建是必需的，从而导致了通用的合成计划，涉及包含由刚性低聚亚苯基间隔基分隔的二甲苯二酰亚胺的多组分系统。

  DOI：

  10.1021/acs.chemmater.5b04602

文献信息

• Energy Transfer at the Single-Molecule Level: Synthesis of a Donor-Acceptor Dyad from Perylene and Terrylene Diimides
  作者：Ha Na Kim、Larissa Puhl、Fabian Nolde、Chen Li、Long Chen、Thomas Basché、Klaus Müllen

  DOI：10.1002/chem.201300439

  日期：2013.7.8

  chosen, considering the solubilities, reactivities, and accessibilities of the building blocks for each individual reaction whilst still using established synthetic techniques, including imidization, Suzuki coupling, and cyclization reactions. The key differentiating consideration in this approach to the synthesis of dyad 1 is the introduction of functional groups in a nonsymmetrical manner onto either

  在2004年，我们报告了基于‐二酰亚胺（PDI）和r二酰亚胺（TDI）二元组（1）的单对荧光共振能量转移（spFRET），该二元组通过刚性取代的对-对-苯基间隔基桥接。从那时起，对该特定化合物进行了进一步的单分子水平研究。在这里，我们专注于此二元组的合成以及可以采用的不同方法。考虑到每个单独反应的结构单元的溶解度，反应性和可及性，选择了优化的反应途径，同时仍使用已建立的合成技术，包括酰亚胺化，Suzuki偶联和环化反应。该方法用于合成二元组的关键区别因素图1是通过酰亚胺化反应以不对称的方式将官能团引入ylene二酰亚胺或三甲苯二酰亚胺上的方法。结合明确的纯化条件，这种改进的方法可以以合理的数量获得高纯度的二元组1。
• Synthesis and Modification of Terrylenediimides as High-Performance Fluorescent Dyes
  作者：Fabian Nolde、Jianqiang Qu、Christopher Kohl、Neil G. Pschirer、Erik Reuther、Klaus Müllen

  DOI：10.1002/chem.200401177

  日期：2005.6.20

  synthetic approaches to terrylenediimides, highly photostable fluorescent dyes, are described. For the first time terrylenediimide has been synthesised in a straightforward procedure that makes large quantities available. The second route includes an efficient cross-coupling reaction followed by a cyclodehydrogenation. Monofunctionalisation of the imide structure allows terrylenediimides now to be coupled

  描述了两种新的合成方法，即高光稳定性的荧光染料-ter二酰亚胺。首次以简单的方法合成了三甲苯二亚胺，该方法可大量使用。第二种途径包括有效的交叉偶联反应，然后进行环脱氢。酰亚胺结构的单官能化使三甲苯二酰亚胺现在可以与多种化合物偶联，例如通过Suzuki交叉偶联，这可以导致一系列带有新官能团（例如羟基，氨基或羧基）的三联二酰亚胺与其他分子。海湾区域中的官能化用于调节三甲苯二酰亚胺的性能并扩大应用范围，例如，通过引入水溶性。
• Terrylenimides: New NIR Fluorescent Dyes
  作者：Frank O. Holtrup、Gert R. J. Müller、Heribert Quante、Steven De Feyter、Frans C. De Schryver、Klaus Müllen

  DOI：10.1002/chem.19970030209

  日期：1997.2

  Terrylenimides 3 and 4 represent a new class of blue colorants, exhibiting absorption maxima at 650 to 700 nm and fluorescence emissions in the NIR region (673 to 750 nm). The terrylenimides were synthesized by means of various organometallic coupling reactions, catalyzed by transition metal complexes (Ni(o) , Pd(o) ) and starting from the aromatic bromides, boronic acids, or organotin compounds. The terrylenimides

  Terrylenimides 3和4代表一类新的蓝色着色剂，在650至700 nm处表现出最大吸收，并在NIR区域（673至750 nm）内发出荧光。通过各种有机金属偶联反应，由过渡金属配合物（Ni（o），Pd（o））催化并从芳香族溴化物，硼酸或有机锡化合物开始合成叔丁基酰亚胺。特里烯酰亚胺具有优异的荧光染料所具有的所有特性：高消光系数，高荧光量子产率以及非常好的热，化学和光化学稳定性。由于其扩展的pi系统，3可以可逆地接受四个负电荷。通过改变取代基，可以修饰3和4以用作可溶性染料或不溶性颜料。
• Synthesis of an Acceptor–Donor–Acceptor Multichromophore Consisting of Terrylene and Perylene Diimides for Multistep Energy Transfer Studies
  作者：Sebastian Stappert、Chen Li、Klaus Müllen、Thomas Basché

  DOI：10.1021/acs.chemmater.5b04602

  日期：2016.2.9

  Motivated by the results obtained from the investigation of singlet–singlet annihilation in a linear multichromophore comprising terrylene diimides (TDI) and perylene diimide (PDI) in 2010, we report the detailed process toward the successful synthesis of a TDI–PDI–TDI dyad. Ineffective synthetic pathways, which were necessary for the understanding of the step-by-step construction of the complex multichromophore

  基于2010年在包含三甲苯二酰亚胺（TDI）和per二酰亚胺（PDI）的线性多发色团中单重态-单态an灭研究的结果，我们报告了成功合成TDI-PDI-TDI二聚体的详细过程。描述了无效的合成途径，这对于理解复杂的多色团的逐步构建是必需的，从而导致了通用的合成计划，涉及包含由刚性低聚亚苯基间隔基分隔的二甲苯二酰亚胺的多组分系统。
• A Simple and Versatile Route to Stable Quantum Dot−Dye Hybrids in Nonaqueous and Aqueous Solutions
  作者：Ting Ren、Prasun K. Mandal、Wolfgang Erker、Zhihong Liu、Yuri Avlasevich、Larissa Puhl、Klaus Müllen、Thomas Basché

  DOI：10.1021/ja8073962

  日期：2008.12.24

  Hybrid systems consisting of core/shell semiconductor quantum dots (QDs) and organic rylene dyes have been prepared and characterized. Complex formation is mediated by bidentate carboxylate moieties covalently linked to the dye molecules. The complexes were very stable with respect to time (at least months), dilution (sub nM), and precipitation. After preparation in organic solvent, complexes could be easily transferred into water. The strong quenching of QD emission by the dye molecules (transfer efficiencies up to 95%) was satisfactorily modeled by an FRET process. Single complexes immobilized in thin polymer films were imaged by confocal fluorescence microscopy.