1,6,7,12-Tetraphenoxyperylene-3,4:9,10-tetracarboxylic acid bisanhydride | 156028-31-8

• 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: 1,6,7,12-Tetraphenoxyperylene-3,4:9,10-tetracarboxylic acid bisanhydride
• 英文别名: 1,6,7,12-tetra(4-phenoxy)perylene-3,4:9,10-tetracarboxylic acid dianhydride；1,6,7,12-tetra-phenoxyperylene tetracarboxylic acid bisanhydride；1,6,7,12-tetra(phenoxy)perylene-3,4:9,10-tetracarboxylic acid dianhydride；1,6,7,12-tetrakis(phenoxy)-3,4:9,10-perylene tetracarboxylic dianhydride；TP-PDA；11,14,22,26-Tetraphenoxy-7,18-dioxaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2(26),3,5(25),9,11,13,15,20,23-decaene-6,8,17,19-tetrone
• CAS: 156028-31-8
• 化学式: C₄₈H₂₄O₁₀
• 分子量: 760.713
• InChiKey: TVOLBNXGGOSFDE-UHFFFAOYSA-N

物化性质

• 密度：
  1.507±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  58
• 可旋转键数：
  8
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,6,7,12-Tetraphenoxyperylene-3,4:9,10-tetracarboxylic acid bisanhydride 在 乙酸铵 作用下， 以 丙酸 为溶剂， 反应 16.0h， 生成 1,6,7,12-Tetraphenoxyperylene-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
• 作为产物：
  描述：

  1,6,7,12-四氯-3,4,9,10-苝四甲酸二酐 在 potassium carbonate 、 potassium hydroxide 作用下， 以 N-甲基吡咯烷酮 、 水 、 异丙醇 为溶剂， 反应 29.0h， 生成 1,6,7,12-Tetraphenoxyperylene-3,4:9,10-tetracarboxylic acid bisanhydride
  参考文献：
  名称：

  一类湾位苯氧基取代的苝酰亚胺荧光染料及其制备方法

  摘要：

  本发明涉及一类湾位苯氧基取代的苝酰亚胺荧光染料及其制备方法。类湾位苯氧基取代的苝酰亚胺荧光染料结构通式如下，通过正丙胺和氯代苝酸酐的缩合反应，提高了反应中间体氯代苝酰亚胺的溶解度。通过苯酚和氯代苝酰亚胺的亲核取代反应，获得了苯氧基取代的苝酰亚胺化合物。将湾位苯氧基修饰的苝酰亚胺水解得到湾位苯氧基修饰的苝酸酐。湾位苯氧基修饰的苝酸酐与三甲基苯胺或三亲水链苯胺缩合，得到最终苝酰亚胺类衍生物。本发明合成方法简单、易于操作、且具有相对较优的溶解性能。含有三亲水链的湾位苯氧基取代的苝酰亚胺染料具有聚集诱导发光行为，在光电和生物传感领域具有较大的应用前景。

  公开号：

  CN110003207A

文献信息

• [EN] 4-OXOQUINOLINE COMPOUNDS<br/>[FR] COMPOSÉS DE 4-OXOQUINOLÉINE
  申请人：BASF SE

  公开号：WO2016083914A1

  公开（公告）日：2016-06-02

  Provided is a 4-oxoquinoline compounds of the formula (I) (I) wherein A is selected from diradicals of the formulae (A.1), (A.2), (A.3), (A.4), (A.5) and (A.6), (A.1) (A.2) (A.3) (A.4) (A.5) (A.6) wherein R 1, R 2a, R 2b, R 3, R 3a, if present R 4a, R 4b, R 5a, R 5b, R 6a, R 6b, R 6c, R 6d, R n1, R n2, R n3, R n4, R m5, R m6, R m7, R m8, R 7, R 8a, R 9 and R 9a are as defined in the claims and in the description. Also provided is a method for their preparation and their use.

  提供的是公式（I）的4-氧代喹啉化合物（I），其中A选自公式（A.1），（A.2），（A.3），（A.4），（A.5）和（A.6）的双基团，（A.1）（A.2）（A.3）（A.4）（A.5）（A.6）其中R1，R2a，R2b，R3，R3a，如果存在R4a，R4b，R5a，R5b，R6a，R6b，R6c，R6d，Rn1，Rn2，Rn3，Rn4，Rm5，Rm6，Rm7，Rm8，R7，R8a，R9和R9a在权利要求书和说明书中定义。还提供了它们的制备方法和使用方法。
• Kinetically Trapped Supramolecular Assembly of Perylene Dianhydride Derivative in Methanol: Optical Spectra, Morphology, and Mechanisms
  作者：Baozhong Lü、Shusen You、Pengyu Li、Chen Li、Klaus Müllen、Meizhen Yin

  DOI：10.1002/chem.201604212

  日期：2017.1.5

  situ DLS and in situ SEM both revealed that the size of the aggregated nanospheres increases with time until the formation of equilibrium H‐aggregates. This shows that TP‐PDA undergoes a kinetically trapped assembly with a rapid transformation into the thermodynamically favored form, and this process can be finely tuned by reducing the concentration and increasing the temperature. Weak intermolecular

  作为纳米科学和纳米技术领域的突破性方法，超分子自组装引起了越来越多的关注。在此，per二酐衍生物（TP-PDA）通过成核生长过程自组装成定义明确的纳米球。通过使用光谱分析，动态光散射（DLS）和扫描电子显微镜（SEM）探索了该过程的机制。原位DLS和原位SEM都表明，聚集的纳米球的大小会随着时间的增长而增加，直到形成平衡的H-聚集体为止。这表明TP‐PDA经历了一个动力学捕获的组装过程，并迅速转变为热力学上有利的形式，并且可以通过降低浓度和提高温度来微调此过程。弱的分子间作用力，例如π–π堆积，氢键和疏溶剂相互作用在纳米结构的形成中起重要作用。这项工作启发了我们探索其他由于动力学原因而被捕获的超分子组装体，由于通常使用的实验时间尺度的捕获时间短，因此很容易被忽略。
• FluorescentJ-type Aggregates and Thermotropic Columnar Mesophases of Perylene Bisimide Dyes
  作者：Frank Würthner、Christoph Thalacker、Siegmar Diele、Carsten Tschierske

  DOI：10.1002/1521-3765(20010518)7:10<2245::aid-chem2245>3.0.co;2-w

  日期：2001.5.18

  A series of perylene tetracarboxylic acid bisimides 3a-e bearing 3,4,5-tridodecyloxyphenyl substituents on the imide N atoms and zero, two, or four phenoxy-type substituents in the bay positions of the perylene core were synthesized. From investigations of their spectroscopic properties and aggregation behavior in low-polarity solvents by absorption and fluorescence optical spectroscopy, not only were

  合成了一系列在亚酰胺N原子上带有3,4,5-三十二烷氧基苯基取代基和在core核的海湾位置具有零，两个或四个苯氧基型取代基的per四羧酸双酰亚胺3a-e。通过吸收光谱和荧光光谱对低极性溶剂的光谱性质和聚集行为的研究，不仅发现这些化合物形成了荧光J型聚集体，而且还可以得出聚集体的结合常数，从而反映了其数量和空间分布双酰亚胺3a-d对苯氧基取代基的需求。在原始状态下，3a-d形成热致六角形柱状中间相，其存在温度范围从低于-30摄氏度到超过300摄氏度。但是，对于四苯氧基取代的化合物3e，发现层状晶体结构。行为上的这种差异可以通过分子的芳香核和周围烷基链的微相分离概念来解释。几种化合物的中间相具有很高的稳定性和明亮的荧光性，使其有希望用作（光）电子器件中的偏振器或组件。
• Synthesis and use of “clickable” bay-region tetrasubstituted perylene tetracarboxylic tetraesters and a perylene monoimide diester as energy acceptors
  作者：Edanur Aydin、Bilal Nisanci、Murat Acar、Arif Dastan、Özgür Altan Bozdemir

  DOI：10.1039/c4nj01565g

  日期：——

  Novel perylene derivatives are ready to be used as functional energy acceptors in light-harvesting systems.

  新型的苝衍生物已经可以用作光合系统中的功能性能量受体。
• Temperature-Responsive Luminescent Solar Concentrators: Tuning Energy Transfer in a Liquid Crystalline Matrix
  作者：Jeroen A. H. P. Sol、Volker Dehm、Reinhard Hecht、Frank Würthner、Albertus P. H. J. Schenning、Michael G. Debije

  DOI：10.1002/anie.201710487

  日期：2018.1.22

  Temperature-responsive luminescent solar concentrators (LSCs) have been fabricated in which the Förster resonance energy transfer (FRET) between a donor-acceptor pair in a liquid crystalline solvent can be tuned. At room temperatures, the perylene bisimide (PBI) acceptor is aggregated and FRET is inactive; while after heating to a temperature above the isotropic phase of the liquid crystal solvent

  温度响应型发光太阳能聚光器（LSC）已经被制造出来，其中液晶溶剂中供体-受体对之间的福斯特共振能量转移（FRET）可以调节。室温下，苝双酰亚胺（PBI）受体聚集，FRET失活；当加热到高于液晶溶剂各向同性相的温度后，受体PBI完全溶解，FRET被激活。这种对 FRET 的不同寻常的温度控制被用来设计颜色可调的 LSC。该设备已被证明对连续的加热和冷却循环高度稳定，使其成为收集未使用的太阳能的有吸引力的设备。