147-14-8Relevant articles and documents
Facile one-pot preparation of thermally and photochemically convertible soluble precursors of copper phthalocyanine and naphthalocyanine
Kikukawa, Yuu,Fukuda, Takamitsu,Fuyuhiro, Akira,Ishikawa, Naoto,Kobayashi, Nagao
, p. 8518 - 8520 (2011)
Soluble copper phthalocyanine (CuPc) and naphthalocyanine (CuNc) precursors which can be converted thermally and photochemically into insoluble CuPc and CuNc, respectively, have been synthesized by a one-step reaction using commercially available chemicals. The Royal Society of Chemistry 2011.
Effect of chain length on thermal conversion of alkoxy-substituted copper phthalocyanine precursors
Fukuda, Takamitsu,Kikukawa, Yuu,Tsuruya, Ryota,Fuyuhiro, Akira,Ishikawa, Naoto,Kobayashi, Nagao
, p. 11832 - 11837 (2011)
A series of dialkoxy-substituted copper phthalocyanine (CuPc) precursors (4a-4d) have been prepared by treating phthalonitrile with the corresponding lithium alkoxide under mild conditions. The precursors exhibited high solubilities in common organic solvents, including acetone, toluene, tetrahydrofuran (THF), CH2Cl2, and CHCl3. Elongation of the alkoxy chains improved the solubilities of the precursors effectively, and accordingly, the butoxy-substituted derivative (4d) showed the highest solubility among 4a-4d. X-ray crystallography clarified that the conjugated skeletons of 4a-4d are all isostructural, and have two alkoxy groups in a syn-conformation fashion, leading to highly bent structures. Thermal conversions of the precursors examined by thermogravimetry (TG) and differential thermal analysis (DTA) demonstrate that 4a was converted into CuPc via two distinct exothermic processes in the 200-250 °C temperature range, while 4d exhibits only one exothermic signal in the DTA. In the field emission scanning electron microscopy (FESEM) images of 4a, the presence of two types of distinct crystal morphology (prismatic and plate-like crystals) can be recognized, implying that the two observed exothermic processes in the DTA can be attributed to the different crystal morphologies of the samples rather than the step-by-step elimination of the alkoxy groups. The thermal formation of CuPc from the precursors has been unambiguously confirmed by X-ray powder diffraction, UV-vis spectroscopy, and elemental analysis. The precursors were converted into CuPc at lower temperature with increasing chain length, presumably because of the increased void volume in the crystals. Thermal conversion performed in the solution phase results in a bright blue-colored solution with prominent absorption bands in the 650-700 nm region, strongly supporting the formation of CuPc.
(Phthalocyaninato)copper(II) complexes fused with different numbers of 15-crown-5 moieties - Synthesis, spectroscopy, supramolecular structures, and the effects of substituent number and molecular symmetry
Sheng, Ning,Zhang, Yuexing,Xu, Hui,Bao, Meng,Sun, Xuan,Jiang, Jianzhuang
, p. 3268 - 3275 (2007)
Symmetrical (phthalocyaninato)copper(II) complexes Cu(Pc′) [Pc′ = Pc(15C5), Pc(opp-15C5)2, Pc(adj-15C5)2, Pc(15C5) 3; Pc = unsubstituted phthalocyaninate, Pc(15C5) = 2,3-(15-crown-5)phthalocyaninate, Pc(opp-15C5)2 = 2,3,16,17-bis(15-crown-5)phthalocyaninate, Pc(adj-15C5)2 = 2,3,9,10-bis(15-crown-5)phthalocyaninate, Pc(15C5)3 = 2,3,9,10,16,17-tris(15-crown-5)phthalocyaninate] (2-5) have been prepared by the reaction of corresponding heteroleptic bis(phthalocyaninato)europium complexes Eu(Pc)(Pc′) [Pc′ = Pc(15C5), Pc(opp-15C5)2, Pc(adj-15C5)2, Pc(15C5)3, Pc(15C5)4; Pc = unsubstituted phthalocyaninate] with Cu(OAc)2 in dry dmf at 100°C. For the purpose of comparative studies, the symmetrical counterparts CuPc (1) and CuPc(15C5)4 [Pc(15C5)4 = 2,3,9,10,16,17,24, 25-tetrakis(15-crown-5)phthalocyaninate] (7) have also been prepared. These monomeric complexes have been characterized by spectroscopic methods in addition to elemental analysis. Having a series of closely related phthalocyanines with a different number and/or disposition of 15-crown-5 groups at the peripheral positions, the effects of 15-crown-5 substituent number and molecular symmetry on the electronic absorption spectra, infra-red (IR) spectra, and supramolecular structure formation induced by K+ ions have been investigated. Systematic studies on the formation of dimeric supramolecular structures of the series of monomers 2-6 reveal and confirm the previously proposed two-step three-stage process of K+-induced dimerization of phthalocyanines with three or four 15-crown-5 moieties. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
A Bipolar and Self-Polymerized Phthalocyanine Complex for Fast and Tunable Energy Storage in Dual-Ion Batteries
Wang, Heng-guo,Wang, Haidong,Si, Zhenjun,Li, Qiang,Wu, Qiong,Shao, Qi,Wu, Lanlan,Liu, Yu,Wang, Yinghui,Song, Shuyan,Zhang, Hongjie
, p. 10204 - 10208 (2019)
Bipolar redox organics have attracted interest as electrode materials for energy storage owing to their flexibility, sustainability and environmental friendliness. However, an understanding of their application in all-organic batteries, let alone dual-ion batteries (DIBs), is in its infancy. Herein, we propose a strategy to screen a variety of phthalocyanine-based bipolar organics. The self-polymerizable bipolar Cu tetraaminephthalocyanine (CuTAPc) shows multifunctional applications in various energy storage systems, including lithium-based DIBs using CuTAPc as the cathode material, graphite-based DIBs using CuTAPc as the anode material and symmetric DIBs using CuTAPc as both the cathode and anode materials. Notably, in lithium-based DIBs, the use of CuTAPc as the cathode material results in a high discharge capacity of 236 mAh g?1 at 50 mA g?1 and a high reversible capacity of 74.3 mAh g?1 after 4000 cycles at 4 A g?1. Most importantly, a high energy density of 239 Wh kg?1 and power density of 11.5 kW kg?1 can be obtained in all-organic symmetric DIBs.
Magneto-modified catalyst on the base of nanocrystalline CuO
Yermakov,Feduschak,Sedoi,Uimin,Mysik
, p. 2445 - 2447 (2004)
The weakly oxidized nanocrystalline copper powders of different sizes (average particle size of 30 and 100nm) were used as the reactants at copper phthalocyanine (PcCu) formation. The nanocrystalline cupric oxide located at the particles surface serves as a heterogeneous magneto-controlled catalyst. A new effect of acceleration of chemical reaction rate controlled by low external steady magnetic field (～2 kOe) at room temperature was revealed and investigated on an example of formation of a coordination compound of PcCu. The rate of PcCu formation accelerated by 7-8 times after applying of a magnetic field.
X-ray analysis of phthalocyanines formed in the reaction of Au-Cu and Au-Sn alloys with 1,2-dicyanobenzene
Kubiak, Ryszard,Janczak, Jan
, p. 107 - 112 (1992)
X-ray investigations of the reactions of copper, tin and their alloys with gold, with 1,2-dicyanobenzene at 210°C have been performed. It was found that under the conditions used, gold does not take part in the reaction with 1,2-dicyanobenzene, but separates from the alloys. Copper and tin phthalocyanines are formed as the main products of the above reactions. The crystal structure of tin phthalocyanine (SnPC) has been determined. SnPc crystallizes in the triclinic system (a = 12.048(3) A, b = 12.630(3) A, c = 8.671(3) A, α = 95.85(5)°, β = 95.10(5)°, γ = 68.25(5)°), space group P1, Z = 2. The refined structure with anisotropic temperature factors have R = 0.041. The Sn atom is coordinated by four isoindole N atoms, the average Sn-N distance being 2.267(6) A. The SnPc molecule is not planar. The Sn atom is 1.1286 A out of the plane of the four coordinating N atoms.
Synthesis and characterization of copper phthalocyanine and tetracarboxamide copper phthalocyanine deposited mica-titania pigments
Topuz, Berna Burcu,Guenduez, Guengoer,Mavis, Bora,Colak, Uener
, p. 31 - 37,7 (2013)
Combination pigments were synthesized by the deposition of copper phthalocyanine and tetracarboxamide copper phthalocyanine on a mica-titania pigment in dimethyl formamide solvent to improve color properties. The FT-IR and XRD analyses were performed to observe the crystal transformations of the pigments on the substrate. The stable beta form of copper phthalocyanine normally preferred in paint applications was obtained at 90 °C and 120°C, while tetracarboxamide copper phthalocyanine remained amorphous at all temperatures experimented. Pigment surface morphologies were investigated by SEM analysis. Copper phthalocyanine crystalline rods were observed on the mica-titania substrate, however, the tetracarboxamide copper phthalocyanine pigment did not exhibit any such crystalline structure due to its amorphous structure, which was confirmed by XRD analysis. Furthermore, nitrogen elemental analysis was performed to determine the amount of copper phthalocyanines adsorbed to the mica-titania surfaces at different temperatures. The resulting combination pigments showed enhanced luster, good dispersion, hue, and high color intensity.
Facile, liquid phase preparation of copper phthalocyanine microcrystals by means of thermal conversion of the dimethoxy-substituted solvent soluble phthalocyanine precursors
Fukuda, Takamitsu,Ishikawa, Naoto
, p. 151 - 154 (2014)
A simple procedure for the preparation of microcrystals of insoluble copper phthalocyanine (CuPc) by thermolysis of a dimethoxy-substituted precursor has been developed. Although the morphologies of the resultant microcrystals are practically independent from initial solution concentrations higher than ca. 0.03 mM of the dimethoxy-precursor, crystals with increased width are obtained with increasing the initial concentration of the precursor.
Improvement in the synthesis of metallophthalocyanines using microwave irradiation
Burczyk, Aleksandra,Loupy, André,Bogdal, Dariusz,Petit, Alain
, p. 179 - 188 (2005)
A successful application of microwave irradiation, in which phthalocyanines were synthesized under solventless conditions from 1,2-phthalonitrile or phthalic anhydride and urea in the presence of metal templates is described. It was found that in comparison with conventional heating, the microwave process is a very useful alternative for cyclotetramerization processes because of reduction of the reaction time, better yield, and easy-to-perform procedure. Graphical Abstract.
SYNTHESIS OF PHTHALOCYANINES FROM PHTHALONITRILE WITH ORGANIC STRONG BASES
Tomoda, Haruhiko,Saito, Shojiro,Ogawa, Shojiro,Shiraishi, Shinsaku
, p. 1277 - 1280 (1980)
In the presence of 1,8-diazabicycloundec-7-ene or 1,5-diazabicyclonon-5-ene, metal-free phthalocyanine was obtained by heating phthalonitrile in alcohols.Addition of a copper(II) salt in the reaction gave copper phthalocyanine in a good yield.
