copper phthalocyanine | 21519-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: copper phthalocyanine
• 英文别名: CuPc
• CAS: 21519-18-6
• 化学式: C₃₆H₂₀CuN₄
• 分子量: 572.128
• InChiKey: QQDGLCXTDMOIJB-XTPDIVBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  cadmium(II) 29H,31H-tetrabenzo[b,g,l,q]porphine 在 copper(II) nitrate 作用下， 以 二甲基亚砜 为溶剂， 生成 copper phthalocyanine
  参考文献：
  名称：

  Metal exchange reactions in cadmium complexes with porphyrins of various structures

  摘要：

  The reaction kinetics of the metal exchange Cd(II)-Cu(II) and Cd(II)-Zn(II) in the cadmium complexes (CdP) with porphyrin ligands (H(2)P) differing by degree of stiffness (tetraphenylporphin, N-methyltetraphenylporphin, and tetraphenyltetrabenzoporphin) in the DMSO medium, was studied using spectrophotometric method. The rate of metal exchange reaction depends on the nature of the non-planatrity of H(2)P in the structure of CdP complexes, as well as on the additional screening of the reaction center MN(4) by the extra-ligands and substituents. The reduction of the coordinating ability of the anion X(-) in the structure of the solvate-salt of incoming metal M'X(2)(Solv) (n-2) in a series: acetylacetonate > acetate > chloride > nitrate favors the metal exchange. In the most studied cases the reaction of CdP proceeds along a combined associative-dissociative mechanism. The order of the metal exchange reaction is found to be depending on temperature indicating a change in the contributions of associative and combined routes. The "pure" associative reaction mechanism in a medium of DMSO was for the first time found for the labile complex CdTPTBP with the saddle-type nonplanar ligand.

  DOI：

  10.1134/s1070363210030254
• 作为试剂：
  描述：

  咪唑 、 3-硝基氯苯 在 copper phthalocyanine 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以77.3%的产率得到1-(3-硝基苯基)-1H-咪唑
  参考文献：
  名称：

  Recyclable hydrophobic copper (II) phthalocyanine catalyzed N-arylation of imidazoles in dimethylsulfoxide

  摘要：

  Copper (II) phthalocyanine (CuPc) was used as a catalyst for the N-arylation of imidazoles with aryl iodides or bromides. The catalyst showed high activity and could be reused 3 times without any significant loss in activity. The catalyst was characterized by Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, and ultraviolet-visible spectroscopy. (C) 2014, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s1872-2067(14)60148-0

文献信息

• 一种溶剂热法制备金属酞菁化合物的方法
  申请人：东北大学

  公开号：CN106496238B

  公开（公告）日：2018-06-26

  一种溶剂热法制备金属酞菁化合物的方法，属于有机合成技术领域。该溶剂热法制备金属酞菁化合物的方法，包括以下步骤：将邻苯二甲腈(C8H4N2)和金属物质加入高压反应釜中，加入溶剂，得到混合物料；其中，按摩尔比， ∶金属物质＝(4～8)∶1，溶剂加入量占高压反应釜内衬容积的2/3～4/5；将混合物料，在160～190℃，进行溶剂热反应2～5h，冷却至室温，倒掉澄清液，干燥，制得粉末状或棒状的金属酞菁化合物，金属酞菁化合物的纯度为98.5％以上。该方法解决现有的金属酞菁化合物晶体的合成存在生长周期长、合成纯度低、成本高等问题，提供的一种溶剂热法制备金属酞菁化合物的方法，具有方法简易，容易操作，且绿色无污染的优点。原料采用金属盐或固态金属均可制备出金属酞菁化合物，在原料选择上范围更大，原料适用性广。
• A new synthesis of benzoporphyrins using 4,7-dihydro-4,7-ethano-2H-isoindole as a synthon of isoindole
  作者：Satoshi Ito、Takashi Murashima、Noboru Ono、Hidemitsu Uno

  DOI：10.1039/a803656j

  日期：——

  Heating 4,7-dihydro-4,7-ethano-2H-isoindole at 200 °C induces the retro-Diels–Alder reaction to give isoindole in essentially quantitative yield, which can be applied to a new synthesis of tetrabenzoporphyrins and monobenzoporphyrins.

  在200℃下加热4,7-二氢-4,7-乙醇-2H-异吲哚会引发逆狄尔斯-阿尔德反应，以基本定量的产率产生异吲哚，可应用于四苯并卟啉和单苯并卟啉的新合成。
• Some peculiarities of metal exchange reactions in porphyrin and phthalocyanine complexes
  作者：D. B. Berezin、O. V. Shukhto、M. S. Nikol?skaya、B. D. Berezin

  DOI：10.1007/s11173-005-0004-7

  日期：2005.2

  The crystal and molecular structures of the K[EuIII (Edta)(H2O)3]·3.5H2O (I) (H4Edta = ethylenediaminetetraacetic acid) and K4[Eu2III(HTtha)2] · 13.5H2O (II) (H6Ttha = triethylenetetraminehexaacetic acid) complexes have been determined by single-crystal X-ray diffraction analyses. The crystal of I belongs to orthorhombic crystal system and Fdd2 space group. The crystal data are as follows: a = 1.9849(6)nm

  K [Eu III（Edta）（H 2 O）3 ]·3.5H 2 O（I）（H 4 Edta =乙二胺四乙酸）和K 4 [Eu 2 III（HTtha）2 ]·的晶体和分子结构13.5H 2 O（II）（H 6 Ttha =三亚乙基四胺六乙酸）络合物已通过单晶X射线衍射分析确定。I的晶体属于正交晶系和Fdd2空间群。晶体数据如下：a = 1.9849（6）nm，b = 3.5598（11）nm，c = 1.2222（4）nm，V = 8.636（5）nm 3，Z = 16，M = 596.37，ρ（计算）= 1.835g / cm 3，µ = 3.166mm-1和F（000）=4752。2936年（I <2.0σ（I））反射的最终R和wR值分别为0.0269和0.0692，所有7284个唯一反射的最终R和wR值分别为0.0317和0.0708。[Eu III（Edta）（H 2 O）3 ]
• Synthesis of extremely soluble precursors of tetrabenzoporphyrins
  作者：Tetsuo Okujima、Yusuke Hashimoto、Guangnan Jin、Hiroko Yamada、Hidemitsu Uno、Noboru Ono

  DOI：10.1016/j.tet.2008.01.014

  日期：2008.3

  This paper describes the preparation of dimethylbicyclo[2.2.2]octadiene-fused porphyrins as extremely soluble precursors of tetrabenzoporphyrins and thermal conversion of the precursors to tetrabenzoporphyrins.

  本文描述了作为二苯并卟啉极易溶的前体的二甲基双环[2.2.2]辛二烯稠合卟啉的制备以及该前体向四苯并卟啉的热转化。
• Effect of copper metalation of tetrabenzoporphyrin donor material on organic solar cell performance
  作者：Michele Guide、Jason D. A. Lin、Christopher M. Proctor、Jingrun Chen、Carlos García-Cervera、Thuc-Quyen Nguyen

  DOI：10.1039/c4ta01068j

  日期：——

  The effects of copper metalation of tetrabenzoporphyrin on the properties and performance of organic solar cells are studied. Tetrabenzoporphyrin (BP) and copper tetrabenzoporphyrin (CuBP) are both solution processed from soluble precursor materials and thermally converted in the thin film. Despite high field-effect hole mobility above 1 cm2 V−1 s−1, the power conversion efficiency (PCE) of solar cell devices with CuBP is severely diminished compared to those with BP. Conducting atomic force microscopy (c-AFM) is used to show that CuBP films are highly conductive in the direction perpendicular to the substrate, relative to those comprising BP. By analyzing the donor absorption characteristics as well as the external quantum efficiency and short-circuit current density of bilayer OPV devices as a function of donor layer thickness, it is determined that the differences in performance are likely due to a prohibitively short effective exciton diffusion length (LD) in the metalated derivative. By modeling the external quantum efficiency of bilayer OPV devices, we are able to approximate this difference in effective LD to be 15 nm for BP and 2 nm for CuBP.

  研究了铜金属化四苯并卟啉对有机太阳能电池特性和性能的影响。四苯并卟啉（BP）和四苯并卟啉铜（CuBP）都是由可溶性前体材料经溶液加工而成，并在薄膜中进行热转换。尽管场效应空穴迁移率高于 1 cm2 V-1 s-1，但与使用 BP 的太阳能电池相比，使用 CuBP 的太阳能电池器件的功率转换效率（PCE）严重降低。传导原子力显微镜（c-AFM）表明，与含有 BP 的薄膜相比，CuBP 薄膜在垂直于基底的方向上具有高导电性。通过分析供体吸收特性以及双层 OPV 器件的外部量子效率和短路电流密度与供体层厚度的函数关系，可以确定性能差异可能是由于金属化衍生物中有效激子扩散长度（LD）过短造成的。通过对双层 OPV 器件的外部量子效率进行建模，我们可以将有效 LD 的差异大致估算为：BP 为 15 nm，CuBP 为 2 nm。