1,6,7,12-Tetra(4-tert-butylphenoxy)perylene-3,4:9,10-tetracarboxylic acid bisimide | 244780-87-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1,6,7,12-Tetra(4-tert-butylphenoxy)perylene-3,4:9,10-tetracarboxylic acid bisimide
• 英文别名: 1,6,7,12-tetra(4-tert-butylphenoxy)perylene-3,4,9,10-tetracarboxylic bisanhydride；11,14,22,26-Tetrakis(4-tert-butylphenoxy)-8,17-dihydroxy-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2(26),3,5(25),7,9,11,13,15,17,20,23-dodecaene-6,19-dione；11,14,22,26-tetrakis(4-tert-butylphenoxy)-8,17-dihydroxy-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2(26),3,5(25),7,9,11,13,15,17,20,23-dodecaene-6,19-dione
• CAS: 244780-87-8
• 化学式: C₆₄H₅₈N₂O₈
• 分子量: 983.173
• InChiKey: RSTWAVVPSLJNIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.1
• 重原子数：
  74
• 可旋转键数：
  12
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  subphthalocyanine 、 1,6,7,12-Tetra(4-tert-butylphenoxy)perylene-3,4:9,10-tetracarboxylic acid bisimide 在 silver trifluoromethanesulfonate 、 N,N-二异丙基乙胺 作用下， 以 甲苯 、 氯仿 为溶剂， 以20%的产率得到
  参考文献：
  名称：

  酞菁电子给体-受体共轭物中由一个B-N键链接的超快光诱导过程∥

  摘要：

  我们通过将这些大环通过单个B-N共价键连接到接受电子的per二酰亚胺或给电子的吩噻嗪上，从而制备了两种不同的亚酞菁共轭物。两个活性结构单元之间的较短间距导致超快的光诱导电子转移反应。

  DOI：

  10.1021/ol302632u
• 作为产物：
  描述：

  1,6,7,12-四叔丁基苯氧基苝-3,4,9,10-四甲酸二酐 在 乙酸铵 作用下， 以 丙酸 为溶剂， 反应 16.0h， 以60%的产率得到1,6,7,12-Tetra(4-tert-butylphenoxy)perylene-3,4:9,10-tetracarboxylic acid bisimide
  参考文献：
  名称：

  Hierarchical Self-Organization of Perylene Bisimide–Melamine Assemblies to Fluorescent Mesoscopic Superstructures

  摘要：

  A series of three perylene tetracarboxylic acid bisimide dyes 3a-c bearing phenoxy substituents at the four bay positions of the perylene core were synthesized and their complexation behavior to complementary ditopic dialkyl melamines 8a-c was investigated. Binding constants and Gibbs binding energies for the hydrogen bonds between the imide and the complementary melamine moiety have been determined in several solvents by NMR and UV/Vis titration experiments with monotopic model compounds 5 and 9. The effects of the solvent polarity and specific solvent-solute interactions on the degree of polymerization of (3.8)(n), are discussed, and a general formula to estimate the chain length of [AA - BB](n) nylon-type supramolecular polymers is derived. In addition to the formation of a hydrogen-bonded supramolecular chain, pi-pi interactions were observed for perylene bisimide - melamine assemblies 3b.8b and 3b.8c in aliphatic solvents. The orthogonal nature of hydrogen bonding and pi-pi interactions leads to three-dimensional growth yielding large-sized aggregates already in dilute solution. On suitable substrates, densely intertwined networks of nano- to mesoscopic strands are formed which have been investigated by electron microscopy, confocal fluorescence microscopy and optical polarization microscopy. The high fluorescence and excellent photostability of these superstructures is promising for future studies on energy migration and artificial light harvesting at the nano- and mesoscopic length scale.

  DOI：

  10.1002/1521-3765(20001103)6:21<3871::aid-chem3871>3.3.co;2-w

文献信息

• Synthesis and Optical Properties of Water-Soluble Polyglycerol-Dendronized Rylene Bisimide Dyes
  作者：Timm Heek、Frank Würthner、Rainer Haag

  DOI：10.1002/chem.201300556

  日期：2013.8.12

  new water‐soluble polyglycerol‐dendronized perylene, terrylene, and quaterrylene bisimides have been synthesized and characterized with respect to their optical properties in polar organic solvents and water by using UV/Vis and fluorescence spectroscopy. All of these dyes were highly soluble in water, but the size of the chosen polyglycerol dendron was only sufficient to completely suppress dye aggregation

  通过使用UV / Vis和荧光光谱法，已经合成了四种新的水溶性聚甘油-二烯化per，三萘嵌苯和四萘嵌苯双酰亚胺，并对其在极性有机溶剂和水中的光学性质进行了表征。所有这些染料都高度溶于水，但是所选聚甘油树枝状分子的大小仅足以完全抑制未取代核的per衍生物的染料聚集。它们在水中的高溶解度以及直至NIR区域的吸收和发射波长，使得未取代核的core和三萘嵌苯双酰亚胺是生物成像应用的理想候选物，而在所有极性溶剂中四萘嵌苯双酰亚胺均没有荧光，因此不值得进一步研究。该生色团在荧光和成像中的应用。
• Synthesis of novel supramolecular triads bearing a H-bonded perylene bisimide core
  作者：Yesudoss Christu Rajan、Muthaiah Shellaiah、Ching-Ting Huang、Hsin-Chieh Lin、Hong-Cheu Lin

  DOI：10.1016/j.tet.2012.07.015

  日期：2012.9

  Two novel hydrogen-bonded (H-bonded) triads consisting of triazine derivatives complexed with a perylene bisimide core were synthesized and characterized. NMR, UV/vis, and fluorescence spectra of these supramolecular triads confirmed the formation of strong multiple H-bonding, which were also proven to be nano-sized H-aggregates by X-ray diffraction (XRD) measurements.

  合成并表征了由三嗪衍生物与per双酰亚胺分子复合而成的两个新颖的氢键合（H键合）三单元组。这些超分子三重核的NMR，UV / vis和荧光光谱证实形成了牢固的多重H键，通过X射线衍射（XRD）测量也证明了它们是纳米级的H聚集体。
• Unconventional hydrogen-bond-directed hierarchical co-assembly between perylene bisimide and azobenzene-functionalized melamine
  作者：Shiki Yagai、Saori Hamamura、Hao Wang、Vladimir Stepanenko、Tomohiro Seki、Kanako Unoike、Yoshihiro Kikkawa、Takashi Karatsu、Akihide Kitamura、Frank Würthner

  DOI：10.1039/b912809c

  日期：——

  Co-assembly of ditopic perylene bisimide and azobenzene-functionalized melamine occurs with an unconventional stoichiometric ratio, providing well-defined nanostructures with a helically-coiled architecture where perylene chromophores are packed in desirable J-type arrangements.

  二聚对苯并芘二酰亚胺和偶氮苯官能化三聚氰胺的共组装以非常规的化学计量比进行，从而形成具有螺旋卷曲结构的明确纳米结构，其中对苯并芘发色团以理想的J型排列方式堆积。
• Hierarchical Self-Organization of Perylene Bisimide–Melamine Assemblies to Fluorescent Mesoscopic Superstructures
  作者：Frank Würthner、Christoph Thalacker、Armin Sautter、Wolfgang Schärtl、Wolfram Ibach、Olaf Hollricher

  DOI：10.1002/1521-3765(20001103)6:21<3871::aid-chem3871>3.3.co;2-w

  日期：2000.11.3

  A series of three perylene tetracarboxylic acid bisimide dyes 3a-c bearing phenoxy substituents at the four bay positions of the perylene core were synthesized and their complexation behavior to complementary ditopic dialkyl melamines 8a-c was investigated. Binding constants and Gibbs binding energies for the hydrogen bonds between the imide and the complementary melamine moiety have been determined in several solvents by NMR and UV/Vis titration experiments with monotopic model compounds 5 and 9. The effects of the solvent polarity and specific solvent-solute interactions on the degree of polymerization of (3.8)(n), are discussed, and a general formula to estimate the chain length of [AA - BB](n) nylon-type supramolecular polymers is derived. In addition to the formation of a hydrogen-bonded supramolecular chain, pi-pi interactions were observed for perylene bisimide - melamine assemblies 3b.8b and 3b.8c in aliphatic solvents. The orthogonal nature of hydrogen bonding and pi-pi interactions leads to three-dimensional growth yielding large-sized aggregates already in dilute solution. On suitable substrates, densely intertwined networks of nano- to mesoscopic strands are formed which have been investigated by electron microscopy, confocal fluorescence microscopy and optical polarization microscopy. The high fluorescence and excellent photostability of these superstructures is promising for future studies on energy migration and artificial light harvesting at the nano- and mesoscopic length scale.
• Ultrafast Photoinduced Processes in Subphthalocyanine Electron Donor–Acceptor Conjugates Linked by a Single B–N Bond
  作者：Carlos Romero-Nieto、Julia Guilleme、Javier Fernández-Ariza、M. Salomé Rodríguez-Morgade、David González-Rodríguez、Tomás Torres、Dirk M. Guldi

  DOI：10.1021/ol302632u

  日期：2012.11.16

  conjugates by linking these macrocycles either to an electron-accepting perylene diimide or to an electron-donating phenothiazine through a single B–N covalent bond. The short spacing between the two active building blocks results in ultrafast photoinduced electron-transfer reactions.

  我们通过将这些大环通过单个B-N共价键连接到接受电子的per二酰亚胺或给电子的吩噻嗪上，从而制备了两种不同的亚酞菁共轭物。两个活性结构单元之间的较短间距导致超快的光诱导电子转移反应。