zinc naphthalocyanine | 26603-12-3

• 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: zinc naphthalocyanine
• 英文别名: ZINC;2,15,28,41,53,55-hexaza-54,56-diazanidatridecacyclo[40.10.1.13,14.116,27.129,40.04,13.06,11.017,26.019,24.030,39.032,37.043,52.045,50]hexapentaconta-1,3,5,7,9,11,13,15,17,19,21,23,25,27(55),28,30,32,34,36,38,40,42(53),43,45,47,49,51-heptacosaene
• CAS: 26603-12-3
• 化学式: C₄₈H₂₄N₈Zn
• 分子量: 778.162
• InChiKey: SYCPYCVMPWZYHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.74
• 重原子数：
  57
• 可旋转键数：
  0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  四溴对烯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 作用下， 以 戊醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 zinc naphthalocyanine
  参考文献：
  名称：

  Photophysical and Photochemical Properties and Aggregation Behavior of Phthalocyanine and Naphthalocyanine Derivatives

  摘要：

  The photophysical and photochemical properties of phthalocyanine and naphthalocyanine with similar structures were studied in solution and with density-functional theory (DFT) computational method. The extended pi-conjugated system in naphthalocyanines causes a bathochromic shift in UV-Vis, emission and excitation bands, and promotes lesser generation of singlet oxygen in solution when compared to phthalocyanines. Time dependent DFT (TD-DFT) calculations point out the molecular orbitals involved in Q-band transition, corresponding to highest occupied molecular orbital (HOMO) to lowest unoccupied molecular orbital (LUMO) transition with a concentration of charge along x-axis, while the transition to LUMO+1 is in y-axis direction. The presence of tert-butyl substituents does not affect the molecular orbitals shape. but affect their energies. Aggregation studies in dimethyl sulfoxide (DMSO):water solutions showed that naphthalocyanines studied have more aggregation tendency than the phthalocyanines. DFT studies indicated that stacked-dimers are preferred to rotated-stacked conformation due the interaction between Zn-II and nitrogen atom from different monomers.

  DOI：

  10.21577/0103-5053.20170215

文献信息

• The impact of the extended π-conjugation in photophysical, photochemical and aggregation behavior of new phthalocyanine–naphthalocyanine hybrids
  作者：Thalita F.M. de Souza、Anderson O. Ribeiro

  DOI：10.1016/j.jphotochem.2017.02.025

  日期：2017.5

  We report the synthesis and characterization of phthalocyanine–naphthalocyanine hybrids and the impact of the extended π-conjugation on the macrocycles aggregation, singlet oxygen production, fluorescence lifetime and quantum yields in solution. We observed that the addition of naphthalol units in the structure causes a bathochromic shift in UV-vis, emission and excitation bands and decreases the quantum

  我们报告了酞菁-萘酞菁杂化物的合成和表征，以及扩展的π-共轭对大环聚集，单线态氧产生，荧光寿命和溶液中量子产率的影响。我们观察到，在结构中添加萘单元会导致UV-vis，发射和激发带发生红移，并降低溶液中单重态氧的量子产率。
• Novel Efficient Preparative Method for Phthalocyanines from Phthalimides and Phthalic Anhydride with HMDS
  作者：Hitoshi Uchida、Paidi Yella Reddy、Shuichi Nakamura、Takeshi Toru

  DOI：10.1021/jo030201w

  日期：2003.10.1

  A convenient synthesis of peripherally substituted or unsubstituted phthalocyanines having a variety of metals is described. Phthalocyanines can be obtained by heating phthalimides or phthalic anhydride with metal salts, hexamethyldisilazane, a catalytic amount of p-TsOH, and DMF at 150 degrees C.

  描述了具有多种金属的周边取代或未取代的酞菁的方便合成。酞菁可通过在150摄氏度下将邻苯二甲酰亚胺或邻苯二甲酸酐与金属盐，六甲基二硅氮烷，催化量的p-TsOH和DMF加热而获得。
• Novel Synthesis of Phthalocyanines from Phthalonitriles under Mild Conditions
  作者：Takeshi Toru、Hitoshi Uchida、Hirokazu Tanaka、Hideyuki Yoshiyama、Paidi Yella Reddy、Shuichi Nakamura

  DOI：10.1055/s-2002-34237

  日期：——

  A convenient preparation of phthalocyanines from phthalonitriles was accomplished by treatment with metal salts and hexamethyldisilazane (HMDS) in DMF at 100 °C. This reaction provides a new preparative method under mild conditions for phthalocyanines having a variety of metals and substituted phthalocyanines as well as Zn-naphthalocyanine.

  通过在 100 °C 的 DMF 中使用金属盐和六甲基二硅氮烷 (HMDS) 进行处理，可以方便地从邻苯二腈中制备酞菁。该反应提供了一种在温和条件下制备多种金属酞菁和取代酞菁以及锌萘酞菁的新方法。
• プラスチック用緑色顔料、それを用いた着色組成物および成形品
  申请人：東洋インキＳＣホールディングス株式会社

  公开号：JP2020180180A

  公开（公告）日：2020-11-05

  【課題】 優れた耐熱性、優れた耐マイグレーション性、および環境衛生性を全て備えたハロゲンフリーのプラスチック用緑色顔料、それを用いた緑色着色組成物、およびプラスチック成形品を提供すること。【解決手段】上記課題は、一般式（１）で示されるナフタロシアニン化合物を必須成分とするプラスチック用緑色顔料により解決される。また、一般式（１）で示されるナフタロシアニン化合物を用いた着色組成物および成形品により解決される。【選択図】なし

  【问题】提供具有卓越耐高温性、卓越耐迁移性和环境卫生性的无卤塑料用绿色颜料，使用该颜料的绿色着色组合物和塑料成型品。 【解决方案】以上问题可通过以一般式（1）表示的萘酰氰化合物作为必需成分的塑料用绿色颜料来解决。此外，使用一般式（1）表示的萘酰氰化合物的着色组合物和成型品也可解决该问题。 【选择图】无
• Synthesis of Non-Symmetrically Benzo-Substituted Phthalocyanines and Their Electronic Spectra
  作者：Yoshihito Ikeda、Hideo Konami、Masahiro Hatano、Katsura Mochizuki

  DOI：10.1246/cl.1992.763

  日期：1992.5

  benzo-substituted phthalocyanine-Zn complexes was isolated from a mixed product of two nitriles(o-phthalonitrile and 2,3-dicyanonaphthalene) and metal salt by chromatographic techniques. The UV-Visible absorption spectra of these compounds showed a schematic variation with the mode of substitution. The “D2h” type complex showed strong anisotropy.

  通过色谱技术从两种腈（邻苯二甲腈和2,3-二氰萘）和金属盐的混合产物中分离出一系列苯并取代酞菁-锌配合物。这些化合物的紫外-可见吸收光谱显示出随取代模式的示意性变化。“D2h”型配合物表现出很强的各向异性。