113684-82-5Relevant academic research and scientific papers
Palladium(II) octaalkoxy- and octaphenoxyphthalocyanines: Synthesis and evaluation as catalysts in the Sonogashira reaction
Platonova, Yana B.,Volov, Alexander N.,Tomilova, Larisa G.
, p. 222 - 227 (2019)
Octaalkoxy- and octaphenoxysubstituted palladium phthalocyanines were used as a new family members of cross-coupling catalysts in the Sonogashira reaction. For the first time it was shown that terminal alkynes reacted mildly with p-substituted aryl bromides in gently conditions at room temperature under Pd and Cu-cocatalysis to give the corresponding phenylacetylenes. This protocol represents the use of palladium phthalocyanines as homogeneous catalysts in the Pd/Cu-promoted Sonogashira reaction.
Predominant effect of connecting atom and position of substituents on azomethine nitrogens' basicity in phthalocyanines
Cidlina, Antonin,Svec, Jan,Ludvová, Lucie,Kune?, Ji?í,Zimcik, Petr,Novakova, Veronika
, p. 1122 - 1133 (2016/12/16)
The basicity of azomethine nitrogens was studied on a series of phthalocyanines (Pcs) that differed in a position of substituent, i.e. peripherally (β-series) and non-peripherally substituted Pcs (a-series), and in a type of substituent (alkylsulfanyl, alkyloxy or alkyl). Appropriate 3,6-or 4,5-disubstituted phthalonitriles were prepared either by nucleophilic substitution or by Negishi coupling. Target zinc Pcs were synthesized by Linstead method. The basicity was studied by the mean of absorption and 1H NMR spectroscopies in chloroform upon titration with trifluoroacetic acid. Equilibrium constants (log K) indicated significant difference within the series. Basicity decreased as follows: α-alkyloxy > α-alkylsulfanyl > β-alkyloxy > β-alkyl > β-alkylsulfanyl ~ α-alkyl with log K higher than 7 down to 2.6 M-1. Increased basicity of a-alkyloxy and a-alkylsulfanyl Pcs is caused by the stabilization of trapped hydrogen at azomethine nitrogen via hydrogen bonding and van der Waals interactions, respectively. The basicity of b-series clearly correlated with the electronic effects of substituents. 1H NMR studies confirmed the possibility of the weak bonding interactions in a-alkyloxy and α-alkylsulfanyl Pcs, however, the position of the 1H NMR signal of azomethine-NH proton was even more influenced by the electronic effects of present substituents than by the weak interactions.
Tetraaryltetraanthra[2,3]porphyrins: Synthesis, structure, and optical properties
Filatov, Mikhail A.,Baluschev, Stanislav,Ilieva, Iliyana Z.,Enkelmann, Volker,Miteva, Tzenka,Landfester, Katharina,Aleshchenkov, Sergey E.,Cheprakov, Andrei V.
, p. 11119 - 11131 (2013/02/26)
A synthetic route to symmetrical tetraaryltetraanthra[2,3]porphyrins (Ar4TAPs) was developed. Ar4TAPs bearing various substituents in meso-phenyls and anthracene residues were prepared from the corresponding pyrrolic precursors. The synthesized porphyrins possess high solubility and exhibit remarkably strong absorption bands in the near-infrared region (790-950 nm). The scope of the method, selection of the peripheral substituents, choice of the metal, and their influence on the optical properties are discussed together with the first X-ray crystallographic data for anthraporphyrin.
Use of long-wavelength electromagnetic radiation and photoprotective tumor localizing agents for diagnosis
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, (2008/06/13)
A process of pathology or target tissue identification comprising administering an imaging material to a pathology or target tissue bearing mammalian host and irradiating the mammalian host with electromagnetic radiation having a wavelength between about
Control of the Discotic to Isotropic Transition in Alkoxy-Substituted Silicondihydroxo-Phthalocyanines by Axial Substituents
Sauer, Thomas,Wegner, Gerhard
, p. 97 - 118 (2007/10/02)
The synthesis of a homologous series of octaalkoxy-substituted silicondihydroxo-phthalocyanines is described.The mesomorphic properties of these new materials were studied by DSC, optical microscopy and X-ray investigations.Compounds with n >/= 4 (n is the number of carbon atoms in a single alkoxy side chain) show a discotic mesophase transition.A transition to the isotropic state is only observed when n >/= 8.X-ray diffraction patterns of the mesophases confirm that all compounds form a hexagonal columnar mesophase of the type Dhd.
Octabutoxyphthalocyanine, a New Electron Donor
Woehrle, Dieter,Schmidt, Volker
, p. 549 - 552 (2007/10/02)
The preparation of the 2,3,9,10,16,17,23,24-octabutoxyphthalocyanine zinc complex (1) is described.The electron-donating groups influence the properties of the compound.The oxidation-reduction potentials studied by cyclic voltammetry in solution shift by ca. 20 mV in the cathodic direction showing easier oxidation and harder reduction of the ligand of (1) compared to unsubstituted phthalocyanines.The interaction with iodine results in the formation of iodine complexes.The electrical conductivities are mentioned.
