2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyanine | 882573-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyanine
• 英文别名: 6,7,15,16,24,25,33,34-Octakis(2,6-dimethylphenoxy)-2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1,3,5,7,9,11,13,15,17,19(39),20,22,24,26,28(38),30(37),31,33,35-nonadecaene；6,7,15,16,24,25,33,34-octakis(2,6-dimethylphenoxy)-2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1,3,5,7,9,11,13,15,17,19(39),20,22,24,26,28(38),30(37),31,33,35-nonadecaene
• CAS: 882573-78-6
• 化学式: C₉₆H₈₂N₈O₈
• 分子量: 1475.76
• InChiKey: YJZZIDVZVNCBAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  24.4
• 重原子数：
  112
• 可旋转键数：
  16
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  183
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyanine 在 zinc diacetate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 15.0h， 以77%的产率得到zinc 2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyanine
  参考文献：
  名称：

  近红外吸收配体氧化的双核酞菁。

  摘要：

  描述了在高消光系数的NIR区（λ= 1000-2200 nm）吸收的配体氧化的环化双核酞菁锌（II）和锂（I）络合物。使用类似的单核Pc复合物进行比较。通过电子吸收，EPR和NMR光谱对溶液中氧化的Pcs进行表征。使用半经验计算的MO图解释了NIR跃迁。酞菁配合物的可逆氧化行为也通过循环伏安法估算。这些新的极长波长吸收性酞菁作为具有新电子特性的材料而引起人们的兴趣。

  DOI：

  10.1002/chem.200601164
• 作为产物：
  描述：

  4,5-bis(2,6-dimethylphenoxy)phthalonitrile 、 1,2,5-硒二唑-3,4-二腈基 在 lithium 作用下， 以 丙醇 为溶剂， 反应 3.0h， 以24%的产率得到
  参考文献：
  名称：

  Homo- and hetero-dinuclear nickel(II), copper(II), and oxidovanadium(IV) complexes of a Schiff-base-fused phthalocyanine with 2,6-dimethylphenoxy and t-butyl groups

  摘要：

  Homo-and hetero-dinuclear nickel(II), copper(II), and oxidovanadium(IV) complexes of a Schiff-base-fused phthalocyanine (pc) with bulky substituents, 2,6-dimethylphenoxy and t-butyl groups, were prepared and characterized. The introduced salen-like Schiff-base unit was shown to affect the spectral feature based on the pc unit in the near infrared region, the Q band being widely split over 600-800 nm. A fairly large ferromagnetic interaction (J = 6.0 cm (1)) was observed for the Cu-II(pc)-Cu-II(salen) homo-dinuclear complex, while an antiferromagnetic interaction (J = -3.2 cm (1)) was observed for the Cu-II(pc)-(VO)-O-IV(salen) hetero-dinuclear complex. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.09.036

文献信息

• Synthesis and Photophysical Properties of Annulated Dinuclear and Trinuclear Phthalocyanines
  作者：Sergey Makarov、Christian Litwinski、Eugeny A. Ermilov、Olga Suvorova、Beate Röder、Dieter Wöhrle

  DOI：10.1002/chem.200500617

  日期：2006.2.1

  mononuclear, dinuclear and trinuclear phthalocyanines were prepared by a mixed cyclotetramerisation of a 1,2,4,5-tetracyanobenzene derivative and 4,5-bis(2,6-dimethylphenoxy)phthalonitrile. For the first time, a pi-electron-conjugated trinuclear phthalocyanine was synthesised with phthalocyanine units connected by common annulated benzene rings. The Q band of the trinuclear compound in solution occurs

  通过将1,2,4,5-四氰基苯衍生物和4,5-双（2,6-二甲基苯氧基）邻苯二甲腈混合环四聚制备无金属的单核，双核和三核酞菁。首次合成了π电子共轭三核酞菁，其酞菁单元通过共同的环苯环连接。溶液中三核化合物的Q谱带出现在λ= 944 nm，而双核和单核化合物的Q谱带分别出现在λ= 853/830和701/664 nm。测定了化合物的荧光量子产率，荧光寿命和单线态氧量子产率。
• Heteroleptic Tetrapyrrole-Fused Dimeric and Trimeric Skeletons with Unusual Non-Frustrated Fluorescence
  作者：Yuehong Zhang、Juwon Oh、Kang Wang、Chao Chen、Wei Cao、Kyu Hyung Park、Dongho Kim、Jianzhuang Jiang

  DOI：10.1002/chem.201504837

  日期：2016.3.18

  two/three‐tetrapyrrole‐fused skeletons behave as one totally π‐conjugated system as a result of the strong conjugative interaction between/among the tetrapyrrole chromophores. In particular, the effectively extended π‐electron system through the fused‐bridge induced strong electronic communication between the Pc and Por moieties and large transition dipole moments in the Pc–Por‐fused systems, providing high

  酞菁（Pc）和卟啉（Por）生色团已通过苯并[ α]融合。]吡嗪部分，产生了前所未有的杂配四吡咯融合的二聚体和三聚体。根据锌二聚体的单晶X射线衍射分析，已清楚地揭示了杂配四吡咯的性质。电化学分析，理论计算和时间分辨光谱结果表明，由于四吡咯发色团之间强烈的共轭相互作用，两个/三个四吡咯稠合的骨架表现为一个完全π共轭体系。特别是，通过熔融桥有效地扩展了π电子系统，从而在Pc和Por部分之间产生了强电子通信，并在Pc-Por熔融系统中产生了较大的跃迁偶极矩，从而提供了较高的荧光量子产率（> 0.13），并且相对而言激发态寿命长（> 1。
• Bis[octakis(2,6-dimethylphenoxy)phthalocyaninato] rare earth(III) complexes: Structure, spectroscopic, and electrochemical properties
  作者：Xiaoli Li、Dongdong Qi、Chao Chen、Liguo Yang、Junshan Sun、Hailong Wang、Xiaoming Li、Yongzhong Bian

  DOI：10.1016/j.dyepig.2013.10.009

  日期：2014.2

  diffraction analysis and electrochemical properties studied by cyclic voltammetry. The electrochemical studies illuminate the electron-withdrawing nature of these substituents in the double-deckers. Density functional theory (DFT) calculations are carried out to further clarify the electron transition nature and orbital information. Based on the structural, spectroscopic, electrochemical and theoretical studies

  同型双（酞菁基）稀土配合物M III [Pc（β-DMPO）8 ] 2 [Pc（β-DMPO）8 ＝ 2、3、9、10、16、17、23、24-辛基（2,6-二甲基苯氧基）酞菁; M = Pr，Nd和Sm]已通过一系列光谱方法进行了合成和表征，包括基质辅助激光解吸/电离飞行时间质谱，核磁共振谱，电子吸收和红外光谱。它们的分子结构已经通过单晶X射线衍射分析和通过循环伏安法研究的电化学性质来确定。电化学研究阐明了双层中这些取代基的吸电子性质。进行密度泛函理论（DFT）计算以进一步阐明电子跃迁性质和轨道信息。根据结构，光谱，电化学和理论研究，
• Annulated Dinuclear Metal-Free and Zn(II) Phthalocyanines: Photophysical Studies and Quantum Mechanical Calculations
  作者：Christian Litwinski、Inés Corral、Eugeny A. Ermilov、Sebastian Tannert、Dmitri Fix、Sergey Makarov、Olga Suvorova、Dieter Wöhrle、Beate Röder

  DOI：10.1021/jp800616r

  日期：2008.7.1

  mononuclear and dinuclear (sharing a common benzene ring) phthalocyanines are presented. A detailed comparison between measured and calculated absorption spectra of all compounds is done, showing a good agreement between theory and experiment. The NH tautomerization for phthalocyanines with an extended pi-electron system was shown for the first time at room temperature. The photophysical properties of all possible

  给出了无金属和Zn（II）单核和双核（共享常见苯环）酞菁的稳态和时间分辨吸收和荧光实验结果以及量子力学密度泛函理论（DFT）计算结果。对所有化合物的测量吸收光谱和计算吸收光谱进行了详细的比较，表明理论和实验之间有很好的一致性。首次在室温下显示具有扩展π电子系统的酞菁的NH互变异构化。不含金属的双核Pc的所有可能的NH互变异构体的光物理性质已得到充分表征。在第一个互变异构体Pc（parallel）中，两对氢原子平行于两个Pc单元的连接线。最低能量Q吸收带的最大值lambda abs Pc（平行）中的λ在832nm处，而荧光最大值的光谱位置在λdaf1 ＝ 837nm处。第二个NH互变异构体Pc（垂直）（lambdaabs = 853 nm，lambdafl = 860 nm）呈现两对垂直于共价轴取向的氢原子，第三个NH P互变异构体Pc（mix）（lambdaabs = 864 nm， Lambdaf1
• Preparation and Optical and Electrochemical Properties of Diphthalocyanine Linked with a TTF Unit
  作者：Takeshi Kimura、Shiduko Nakajo、Shomu Sasaki

  DOI：10.3987/com-16-s(s)55

  日期：——

  4,4',7,7 '-Tetrabuty1-5,5',6,6'-tetracyano-2,2'-bis(benzo-1,3-dithio12-ylidene) (3-Bu) was prepared and mixed with 4,5-bis(2,6-dimethylphenoxy)-phthalonitrile (4), which was treated with lithium alkoxide at 120 C to produce diphthalocyanine linked with a TTF unit. The structure of the product was determined by NMR and MALDI-TOF-MS. The optical and electrochemical properties were examined by UV-vis spectra and cyclic voltammetry.