14320-04-8Relevant articles and documents
The solid phase, room-temperature synthesis of metal-free and metallophthalocyanines, particularly of 2,3,9,10,16,17,23,24-octacyanophthalocyanines
Nemykin, Victor N.,Kobayashi, Nagao,Mytsyk, Vladislav M.,Volkov, Sergey V.
, p. 546 - 547 (2000)
Room-temperature synthesis of phthalocyanines (pcs) by condensation of phthalonitriles in the presence of solid sodium methoxide in THF is proposed for the synthesis of metal-free pcs with temperature- and/or base-sensitive substituents. The addition of metal salts after metal-free pc formation in the same vessel produces metallopcs in moderate to high (ca. 30-90%) yields.
Synthesis and Aggregation Studies of Functional Binaphthyl-Bridged Chiral Phthalocyanines
Revuelta-Maza, Miguel á.,Torres, Tomás,Torre, Gema De La
, p. 8183 - 8186 (2019)
We describe the preparation of a battery of chiral Zn(II) phthalocyanines with an AABB substitution pattern through cross-condensation of different chiral, binaphthyloxy-linked bisphthalonitriles and (non)functionalized single phthalonitriles. All the compounds are endowed with reactive groups (halogen and/or ethynyl moieties) that will allow us to prepare customized amphiphilic phthalocyanines. Preliminary self-assembly studies in solution have been performed by UV-vis and circular dichroism experiments.
Novel synthesis of phthalocyanines from phthalonitriles under mild conditions
Uchida, Hitoshi,Tanaka, Hirokazu,Yoshiyama, Hideyuki,Reddy, Paidi Yella,Nakamura, Shuichi,Toru, Takeshi
, p. 1649 - 1652 (2002)
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.
Synthesis, crystal structure and characterization of a new zinc phthalocyanine complex
Cui, Li-Ying,Yang, Jin,Fu, Qiang,Zhao, Bao-Zhong,Tian, Lei,Yu, Hai-Ling
, p. 149 - 154 (2007)
A new complex [ZnPc(H2O)]·2DMF (1), where Pc = phthalocyanine and DMF = N,N-dimethylformamide, has been synthesized and its crystal has been determined by single-crystal X-ray diffraction method. The compound crystallizes in the triclinic space group P - 1. The lattice parameters are a = 11.668(5) A?, b = 12.186(5) A?, c = 13.939(6) A?, α = 78.697(7)°, β = 88.045 (7)°, γ = 62.949(7)°, V = 1727.4(12) A?3 and Z = 2. The Zn(II) ion is five-coordinated by four nitrogen atoms from Pc ligands and one oxygen atom from one water molecule. Notably, there are strong π-π interactions between Pc ligands, leading to 1D superamolecular structure. Moreover, the elemental analyses, FT-IR, UV-vis and Fluorescence spectra for this complex were also determined.
Electrochemistry of metal phthalocyanines in organic solvents at variable pressure
Yu, Bazhang,Lever,Swaddle, Thomas W.
, p. 4496 - 4504 (2004)
High-pressure electrochemical investigations of representative metallophthalocyanines in solution are reported. The selected systems were ZnPc, CoPc, FePc, and CoTNPc (Pc = phthalocyanine, TNPc = tetraneopentoxyphthalocyanine) in several donor solvents and (for CoTNPc) dichlorobenzene, with [Bu4N][ClO4] as supporting electrolyte and a conventional Pt electrode referred to Ag+(CH 3CN)/Ag. Electrode reaction volumes ΔVcell for CoTNPc and ZnPc show that consecutive ring reductions result in progressive increases in electrostriction of solvent in accordance with Drude-Nernst theory. Reductions of the metal center in CoTNPc and CoPc, however, result in much less negative values of ΔVcell than would be expected by analogy with ring reductions of the same charge type. This is attributable to loss of axial ligands following the insertion of antibonding 3dz2 electrons on going from CoIII to low-spin CoII and then CoI. In the same vein, rate constants for reduction of Co III centers to CoII were an order of magnitude slower than those for other metal center or phthalocyanine ring reductions because of Franck-Condon restrictions. The volumes of activation ΔV el? were invariably positive for all the electrode reactions and in most cases were roughly equal to the volumes of activation for reactant diffusion ΔVdiff?, indicating predominant rate control by solvent dynamics rather than by activation in the manner of transition-state theory for which negative ΔVel? values are expected. For CoTNPc and CoPc in donor solvents, the ΔVcell and ΔVel? data are consistent with the assignments of the successive reduction steps made for CoTNPc in DMF by Nevin et al. (Inorg. Chem. 1987, 26, 570).
Electronic energy levels of organic dyes on silicon: A photoelectron spectroscopy study of ZnPc, F16ZnPc, and ZnTPP on p-Si(111):H
Weiler, Ulrich,Mayer, Thomas,Jaegermann, Wolfram,Kelting, Christian,Schlettwein, Derck,Makarov, Sergey,Woì?hrle, Dieter
, p. 19398 - 19403 (2004)
Alignment of energy levels and chemical interaction of the organic pigments ZnPc, substituted F16ZnPc, and ZnTPP on H-terminated Si(111) have been deduced from valence band and core level photoelectron spectroscopy with high surface sensitivity for coverage below and in the monolayer region. Hydrogen-terminated Si(111) was prepared in UHV. The dyes have been purified by zone sublimation and were deposited at room temperature by PVD. SXPS taken at the synchrotron BESSY shows physisorption of the dye molecules; chemical shifts indicating strong interactions with the substrate have not been observed. The maxima of the HOMO photoemission of ZnPc, F16ZnPc, and ZnTPP are measured at 0.45, 1.55, and 1.0 eV below the Si valence band maximum. These experimental values are compared to theoretical values and are related to the position of the optical gap, the transport gap, and the redox potentials of the ground and excited state.
Zn phthalocyanine/carbon nitride heterojunction for visible light photoelectrocatalytic conversion of CO2 to methanol
Zheng, Jingui,Li, Xiaojie,Qin, Yuhu,Zhang, Shuqin,Sun, Mingsheng,Duan, Xiaoguang,Sun, Hongqi,Li, Peiqiang,Wang, Shaobin
, p. 214 - 223 (2019)
Zinc phthalocyanine/carbon nitride nanosheets photoelectrocatalysts were obtained by evaporation and calcination of the mixture of ZnPc and carbon nitride. It exhibits highly efficient synergistic function between PC-CO2RR and EC-CO2RR. The energy band matching between the ZnPc and carbon nitride results in the faster electrons transfer and less electron-hole pairs recombination. The optimized ZnPc/carbon nitride at a ratio of 0.1 wt% demonstrates high efficiency in photoelectrocalytic reduction of CO2 under visible light, generating a major product of methanol at a yield of 13 μmol·cm?2 after 8 h. The efficiency of photoelectrocalytic reduction of CO2 to methanol is 2.6 times as high as that of electrocatalytic CO2 reduction reaction, and 5.9 times as high as that of photocatalytic CO2 reduction reaction. The mechanism of the photoelectrocatalytic CO2 reduction reaction to methanol was discussed in detail.
Preparation of non-substituted metal phthalocyanines at low temperature using activated Rieke zinc and magnesium
Kharisov,Garza-Rodriguez,Leija Gutierrez,Ortiz Mendez,Garcia Caballero,Tsivadze
, p. 755 - 760 (2005)
Synthesis of non-substituted metal phthalocyaninates starting from phthalonitrile in various alcohols in presence of chemically activated Rieke zinc and magnesium in three forms (ordinary magnesium turnings, activated Rieke magnesium and complex Mg(anthracene)·3THF) at low temperatures (20-50°C) is described. It is shown that the presence of active elemental metal causes a rapid PcM formation in low-weight alcohols. Copyright
Chemically reversible reactions of hydrogen sulfide with metal phthalocyanines
Hartle, Matthew D.,Sommer, Samantha K.,Dietrich, Stephen R.,Pluth, Michael D.
, p. 7800 - 7802 (2014)
Hydrogen sulfide (H2S) is an important signaling molecule that exerts action on various bioinorganic targets. Despite this importance, few studies have investigated the differential reactivity of the physiologically relevant H2S and
Zinc phthalocyanine coupled with UIO-66 (NH2) via a facile condensation process for enhanced visible-light-driven photocatalysis
Liang, Qian,Zhang, Miao,Zhang, Zhihui,Liu, Changhai,Xu, Song,Li, Zhongyu
, p. 123 - 130 (2017)
Metal-organic frameworks (MOFs) have shown a great potential for water treatment as an environmentally friendly photocatalyst. In this work, a zirconium based MOF, UIO-66 (NH2) covalently coupled with zinc phthalocyanine (ZnTCPc) was prepared via a facile condensation process. Compared with the mixture of ZnTCPc and UIO-66 (Zr) by impregnation, ZnTCPc/UIO-66 (NH2) presented an enhanced photocatalytic activity for the degradation of methylene blue (MB) under visible-light irradiation. The formation of strong covalent bonds and synergistic integration between ZnTCPc and UIO-66 (NH2) was proved by characterization results such as transmission electron microscopy, X-ray photoelectron spectra and Fourier transform infrared spectroscopy. Additionally, ZnTCPc/UIO-66 (NH2) photocatalyst retained excellent stability after five recycles, and the photocatalytic mechanism was investigated systematically. This work demonstrates a high potential of using porous MOFs-based materials not only as supports but as electron acceptors to trigger the reaction for coupling MOFs with dye, fabricating novel MOFs-dye nanocomposite systems and enhancing their photostability and photocatalytic activity.
