2,3-dicyano-5,6-bis(4-hydroxyphenyl)pyrazine | 935249-88-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,3-dicyano-5,6-bis(4-hydroxyphenyl)pyrazine
• 英文别名: 5,6-bis(4-hydroxyphenyl)pyrazine-2,3-dicarbonitrile
• CAS: 935249-88-0
• 化学式: C₁₈H₁₀N₄O₂
• 分子量: 314.303
• InChiKey: VPYUPECLLOSHOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-dicyano-5,6-bis(4-hydroxyphenyl)pyrazine 、 3,4,5-tris(4-dodecyloxybenzyloxy)benzoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以59%的产率得到2,3-dicyano-5,6-bis-4-[3,4,5-tris-(4-dodecyloxybenzoyloxy)-benzoyloxy]phenyl pyrazine
  参考文献：
  名称：

  Synthesis and optical/thermal properties of low molecular mass V-shaped materials based on 2,3-dicyanopyrazine

  摘要：

  A novel series of luminescent low molecular mass materials containing a 2,3-dicyanopyrazine central core were synthesized through an esterification reaction between diphenol 10 and different aromatic carboxylic acids 1-6, containing terminal long alkyl chains. They have a similar V-shaped geometry with lack of planarity between the two arms, confirmed by the X-ray structure of the central core. The optical and thermal properties of these compounds were evaluated. They show blue fluorescence in solution (lambda(max)(em) 440-480 nm) with quantum fluorescence yields (Phi(F)) from 0.003 to 0.1 and Stokes shifts of around 90 nm. In solid state, optical band gaps (E-g) were from 3.14 to 3.32 eV. Thin films of 11, 13, and 14 exhibited blue fluorescence (lambda(max)(em) 430-456 nm), and 12,15, and 16 (more bulky) displayed green fluorescence (lambda(max)(em) 488-512 nm). Most of the materials exhibited good thermal stability, exhibiting an amorphous glassy state after melting. Transparent amorphous films were easily obtained through spin coating and characterized by AFM analysis. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.045
• 作为产物：
  描述：

  茴香偶姻 在 硝酸铵 、 氢溴酸 、 copper diacetate 作用下， 以 溶剂黄146 为溶剂， 反应 98.0h， 生成 2,3-dicyano-5,6-bis(4-hydroxyphenyl)pyrazine
  参考文献：
  名称：

  四吡嗪并卟啉镁：调节红色荧光pH指示剂的p K a †

  摘要：

  镁（II）tetrapyrazinoporphyrazines（TPyzPzs）是优异的红色荧光团（λ ˚F〜663纳米，Φ ˚F〜0.53在THF中）。在这项工作中，准备了一系列带有一个或两个酚取代基的不对称TPyzPzs的镁（II）配合物。酚部分的适当取代可调节其p K a在5.5至13的范围内。酚基团在较高pH值下的去质子化会在大环中诱导强供体（酚盐），从而导致这些指示剂的红色荧光的pH依赖性猝灭。在将TPyzPzs掺入两种乳状液和脂质体两种输送系统后，水溶液中的pH感测得到了证实。后者还充当生物膜的简单模型。最后，通过将TPyzPz指示剂和亲脂性pH不敏感的BODIPY染料掺入脂质体中，构建了波长比探针。TPyzPzs的合成前体，即取代的2,3-二嗪吡嗪，也代表了供体-受体系统，肉眼很容易看到吸收光谱的pH依赖性变化。

  DOI：

  10.1039/c9dt00381a

文献信息

• Synthesis and singlet oxygen generation of pyrazinoporphyrazines containing dendrimeric aryl substituents
  作者：Adam Tillo、Dariusz T. Mlynarczyk、Lukasz Popenda、Barbara Wicher、Michal Kryjewski、Wojciech Szczolko、Stefan Jurga、Jadwiga Mielcarek、Maria Gdaniec、Tomasz Goslinski、Ewa Tykarska

  DOI：10.1039/c6nj03886g

  日期：——

  their potential applications in photodynamic therapy. The macrocycles were obtained via Linstead macrocyclization with good yields. The expansion of the porphyrazine periphery with hyperbranched aryl substituents was beneficial in terms of purification and isolation of compounds, effectively hampering their aggregation tendency in different concentrations. The obtained macrocycles were assessed for their

  合成了吡嗪并卟啉和三苯并吡嗪并卟啉，并研究了它们在光动力疗法中的潜在应用。大环通过Linstead大环化，收率高。具有高支化芳基取代基的卟啉嗪外围的扩展在化合物的纯化和分离方面是有益的，有效地抑制了它们在不同浓度下的聚集趋势。对获得的大环化合物的单线态氧生成量子产率进行了评估，并发现三苯并吡嗪并卟啉比吡嗪并卟啉要好得多。比较两种2，3-二氰基吡嗪衍生物的晶体堆积，发现超分子结构的重复基序是由芳族吡嗪与反转中心相关分子的苯环之间的π-π堆积相互作用形成的二聚体。