cobalt phthalocyanine tetracarboxamide | 69934-87-8

• 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: cobalt phthalocyanine tetracarboxamide
• 英文别名: (2,9,16,23-tetracarboxamidophthalocyanato)cobalt(II)；Cobalt(2+);2,11,20,29,37,39-hexaza-38,40-diazanidanonacyclo[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(18),14,16,19(39),20,22(27),23,25,28,30(37),31(36),32,34-nonadecaene-6,15,24,33-tetracarboxamide；cobalt(2+);2,11,20,29,37,39-hexaza-38,40-diazanidanonacyclo[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(18),14,16,19(39),20,22(27),23,25,28,30(37),31(36),32,34-nonadecaene-6,15,24,33-tetracarboxamide
• CAS: 69934-87-8
• 化学式: C₃₆H₂₀CoN₁₂O₄
• 分子量: 743.626
• InChiKey: VVXNISPTVYJSFM-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  53
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  249
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  cobalt phthalocyanine tetracarboxamide 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到(2,9,16,23-tetracyanophthalocyanato)cobalt(II)
  参考文献：
  名称：

  Crown Ether Substituted Monomeric and Cofacial Dimeric Metallophthalocyanines. 2. Photophysical Studies of the Cobalt(II) and Nickel(II) Variants

  摘要：

  Metallophthalocyanines have been prepared with 18-crown-6 residues at the peripheral benzo sites (McrPc). Metal centers employed have been H-2 (free base), Zn(II), Cu(LT), Co(II), and Ni(II). In the present report, the Co(II) and Ni(II) systems are considered; the other three compounds were considered in part 1 of this series of papers. Ultrafast transient absorption spectrography was employed to examine the dynamic properties of the excited electronic states of the monomers and dimers. Under pulsed photoexcitation conditions, the most prominent feature in the transient absorption spectrum of all systems studied was a transient bleaching at the ground-state absorption maxima. The time profiles for ground-state repopulation of photoexcited McrPc and McrPcD where M = Co(II) and Ni(II) were best described with double-exponential kinetics with lifetimes of 1.3 and 7.6 ps for CocrPc; 0.8 and 7.2 ps for CocrPcD; 3.2 and 12.8 ps for NicrPc; 2.2 and 24.2 ps for NicrPcD, respectively. An analysis of the kinetic data in the case of the Co(II) and Ni(II) Pc monomers and dimers indicated that the initially formed (1)pi,pi*-singlet state decayed via parallel processes into either a short-lived (3)pi,pi*-triplet state (absorbing maximally around 540 nm) or a vibrationally hot, electronically excited, metal-centered (d,d) state. A rapid blue spectral shift (tau = 1.3 ps) at the red side of the ground-state bleaching band was attributed to vibrational cooling of this latter state. This very rapid rate of cooling of the vibrationally hot metal state indicates that it may be determined by the rate of energy translocation through the M-N bonds to the sc-system, and not into the solvent, viz., an intramolecular process. The repopulation dynamics were shown to be independent of whether excitation was at 400 nm (initial formation of an upper excited state) or at 645 nm (initial formation of the lowest excited state), thus indicating that the internal conversion process, S-2(pi,pi*) --> S-1(pi,pi*), was occurring within the time resolution of the instrument (ca. 500 fs).

  DOI：

  10.1021/jp991166t
• 作为产物：
  描述：

  尿素 、 cobalt(II) chloride 、 偏苯三酸酐 在 hexaammonium heptamolybdate tetrahydrate 作用下， 以 硝基苯 为溶剂， 反应 3.0h， 以86%的产率得到cobalt phthalocyanine tetracarboxamide
  参考文献：
  名称：

  金属酞菁在有机-无机杂化囊泡“Cerasome”中催化硫代乙二醇的好氧氧化

  摘要：

  摘要 嵌入陶瓷体中的疏水化金属酞菁衍生物的分子组装体是一种具有脂质双层和二氧化硅表面的有机-无机杂化囊泡，是硫甘醇有氧氧化的有效催化剂。催化活性高于十六烷基2-羟基-3-氯丙基磷酸酯囊泡、十二烷基硫酸钠胶束、乙醇和苯。

  DOI：

  10.1016/j.inoche.2020.107866
• 作为试剂：
  描述：

  对二甲苯 在 N-羟基邻苯二甲酰亚胺 、 cobalt phthalocyanine tetracarboxamide 、 氧气 、 溶剂黄146 作用下， 以83.6 %的产率得到对甲基苯甲酸
  参考文献：
  名称：

  一种协同催化体系氧化对二甲苯制备对甲基苯甲酸的方法

  摘要：

  本发明涉及一种协同催化体系氧化对二甲苯制备对甲基苯甲酸的方法，包括：取对二甲苯、NHPI以及CoPc(CONH2)4分散于有机溶剂中，然后在氧气条件下反应得到目的产物。本发明是在NHPI/CoPc(CONH2)4的协同催化作用下，以及分子氧存在下催化氧化对二甲苯制备对甲基苯甲酸，该反应使用NHPI/CoPc(CONH2)4的协同催化体系作为催化剂，采用一锅合成法，制备步骤较少，此催化剂加入反应体系大大提高了对二甲苯的转化率，且反应几乎无副产物生成，且所用氧化剂氧气来源广泛、廉价易得，降低了反应成本，实现了该反应的绿色化学过程。与现有技术相比，本发明使用的催化剂对环境友好，成本较低，且催化效果良好，对甲基苯甲酸的产率较高，反应条件较温和。

  公开号：

  CN115215739A

文献信息

• Improved Synthesis of Soluble Metal-Free/Metal Phthalocyanine Tetracarboxylic Acids and Their Application in the Catalytic Epoxidation of Cyclohexene
  作者：Xiaoling Sun、Li Wang、Zhi Tan

  DOI：10.1007/s10562-015-1500-0

  日期：2015.4

  selectivity of cyclohexene oxide. Metal-free phthalocyanine tetracarboxylic acid (5) and metal (copper (II), iron (III), and cobalt (II)) phthalocyanine tetracarboxylic acids (6–8, respectively) were compared. Complexes 6–8 exhibited higher catalytic activity than compound 5 under the optimal conditions.Graphical AbstractFour soluble metal-free and metal PTCs were synthesized using a novel method, and were

  摘要 使用基于重氮反应改进水解的新方法合成了不含可溶性金属和金属（铜 (II)、铁 (III) 和钴 (II)）酞菁四羧酸 (5-8)。所得化合物（5-8）通过 X 射线衍射、紫外-可见光谱和 FT-IR 光谱表征，然后用作催化剂以分子氧为氧化剂进行环己烯的环氧化。优化反应条件，包括反应时间、温度、催化剂用量和异丁醛/环己烯比，以实现最高的氧化环己烯选择性。比较了不含金属的酞菁四羧酸 (5) 和金属（铜 (II)、铁 (III) 和钴 (II)）酞菁四羧酸（分别为 6–8）。配合物6-8在最佳条件下表现出比化合物5更高的催化活性。图文摘要采用新方法合成了四种可溶性无金属和金属PTCs，并将其用作环己烯环氧化反应的催化剂，分子氧为氧化剂。在最佳条件下，共实现了58.1%的氧化环己烯选择性和收率。
• Cobalt phthalocyanine tetracarboxylic acid modified reduced graphene oxide: a sensitive matrix for the electrocatalytic detection of peroxynitrite and hydrogen peroxide
  作者：Ioana S. Hosu、Qian Wang、Alina Vasilescu、Serban F. Peteu、Valentin Raditoiu、Svetlana Railian、Vladimir Zaitsev、Kostiantyn Turcheniuk、Qi Wang、Musen Li、Rabah Boukherroub、Sabine Szunerits

  DOI：10.1039/c4ra09781e

  日期：——

  peroxynitrite (ONOO−, PON) and hydrogen peroxide (H2O2) is intrinsically difficult as both species show similar oxidative features located within a narrow potential. The sub-second lifetime of ONOO− at neutral pH further complicates the analysis. In this paper, we examine the electrocatalytic activity of cobalt phthalocyanine tetracarboxylic acid (CoPc–COOH) loaded reduced graphene oxide (rGO) films towards

  过氧亚硝酸盐的定量（ONOO -，PON）和过氧化氢（H 2 ö 2）在本质上是困难的，因为这两个物种显示出类似的氧化位于一个窄的潜在内的特征。亚秒级生命周期-在中性pH下进一步使分析复杂化。在本文中，我们研究了负载钴酞菁四羧酸（CoPc–COOH）的还原氧化石墨烯（rGO）膜对过氧亚硝酸盐和过氧化氢检测的电催化活性。rGO / CoPc-COOH基质是通过氧化石墨烯（GO）和CoPc-COOH在90°C下超声处理5 h合成的。X射线光电子能谱，FTIR，拉曼光谱，紫外可见光谱和电化学证实了CoPc-COOH的整合以及GO还原为rGO的作用。所述RGO /酞菁钴-COOH膜表现出对ONOO高的电催化活性和特异性-在阳极电势与≈11.5±1 nA的nM的灵敏度-1过氧亚硝酸盐的检出限约为1.7 nM。rGO / CoPc-COOH薄膜进一步表现出H 2 O 2的电催化还原，灵敏度为14.5μAmM
• Highly Efficient, Mild, Bromide-Free and Acetic Acid-Free Dioxygen Oxidation of <i>p</i>-Nitrotoluene to <i>p</i>-Nitrobenzoic Acid with Metal Phthalocyanine Catalysts
  作者：Xufeng Song、Yuanbin She、Hongbing Ji、Yanhui Zhang

  DOI：10.1021/op049810b

  日期：2005.5.1

  and characterized by elemental analysis and mass spectrometry. p-Nitrobenzoic acid was efficiently prepared in high yield from bromide-free and acetic acid-free aerobic oxidation of p-nitrotoluene using metal phthalocyanines as catalysts under mild conditions in alkali−methanol solution. Up to 88.8% isolated yield of p-nitrobenzoic acid was obtained with the catalysis of tetracarboxyl phthalocyanine

  合成了四种金属四羧基酞菁，并通过元素分析和质谱表征。在碱性甲醇溶液中，在温和条件下，使用金属酞菁作为催化剂，由对硝基甲苯的无溴和无乙酸好氧氧化反应，可以高效，高产率地制备对硝基苯甲酸。通过四羧基酞菁钴（0.13 mol％，基于p的摩尔数）的催化，获得高达88.8％的对硝基苯甲酸的分离产率。-硝基甲苯）任选与少量二甲基甲酰胺在2.0 MPa二氧存在下于30-60°C混合。基于金属配位化学理论，进一步讨论了引入酞菁环中的羧基对催化性能的影响。
• Aerobic oxidation of thioglycol catalysed by metallophthalocyanine in an organic-inorganic hybrid vesicle “cerasome”
  作者：Guolin Zhang、Li Zhang、Dan Zhang、Qiuhua Wu、Yoshihiro Sasaki、Yoshio Hisaeda、Kazuma Yasuhara、Jun-ichi Kikuchi、Xi-Ming Song

  DOI：10.1016/j.inoche.2020.107866

  日期：2020.5

  Abstract A molecular assembly of a hydrophobized metallophthalocyanine derivative embedded in a cerasome, an organic–inorganic hybrid vesicle with a lipid bilayer and silica surface, was a potent catalyst for aerobic oxidation of thioglycol. The catalytic activity was higher than those in hexadecyl 2-hydroxy-3-chloropropyl phosphate vesicles, sodium dodecylsulfate micelles, ethanol, and benzene.

  摘要 嵌入陶瓷体中的疏水化金属酞菁衍生物的分子组装体是一种具有脂质双层和二氧化硅表面的有机-无机杂化囊泡，是硫甘醇有氧氧化的有效催化剂。催化活性高于十六烷基2-羟基-3-氯丙基磷酸酯囊泡、十二烷基硫酸钠胶束、乙醇和苯。
• Crown Ether Substituted Monomeric and Cofacial Dimeric Metallophthalocyanines. 2. Photophysical Studies of the Cobalt(II) and Nickel(II) Variants
  作者：A. V. Nikolaitchik、M. A. J. Rodgers

  DOI：10.1021/jp991166t

  日期：1999.9.1

  Metallophthalocyanines have been prepared with 18-crown-6 residues at the peripheral benzo sites (McrPc). Metal centers employed have been H-2 (free base), Zn(II), Cu(LT), Co(II), and Ni(II). In the present report, the Co(II) and Ni(II) systems are considered; the other three compounds were considered in part 1 of this series of papers. Ultrafast transient absorption spectrography was employed to examine the dynamic properties of the excited electronic states of the monomers and dimers. Under pulsed photoexcitation conditions, the most prominent feature in the transient absorption spectrum of all systems studied was a transient bleaching at the ground-state absorption maxima. The time profiles for ground-state repopulation of photoexcited McrPc and McrPcD where M = Co(II) and Ni(II) were best described with double-exponential kinetics with lifetimes of 1.3 and 7.6 ps for CocrPc; 0.8 and 7.2 ps for CocrPcD; 3.2 and 12.8 ps for NicrPc; 2.2 and 24.2 ps for NicrPcD, respectively. An analysis of the kinetic data in the case of the Co(II) and Ni(II) Pc monomers and dimers indicated that the initially formed (1)pi,pi*-singlet state decayed via parallel processes into either a short-lived (3)pi,pi*-triplet state (absorbing maximally around 540 nm) or a vibrationally hot, electronically excited, metal-centered (d,d) state. A rapid blue spectral shift (tau = 1.3 ps) at the red side of the ground-state bleaching band was attributed to vibrational cooling of this latter state. This very rapid rate of cooling of the vibrationally hot metal state indicates that it may be determined by the rate of energy translocation through the M-N bonds to the sc-system, and not into the solvent, viz., an intramolecular process. The repopulation dynamics were shown to be independent of whether excitation was at 400 nm (initial formation of an upper excited state) or at 645 nm (initial formation of the lowest excited state), thus indicating that the internal conversion process, S-2(pi,pi*) --> S-1(pi,pi*), was occurring within the time resolution of the instrument (ca. 500 fs).