Novel peripherally and non-peripherally hydrobenzoin substituted optically active phthalocyanines: Synthesis, characterization, aggregation, electrochemical properties and catalytic applications

Oxidation of benzyl alcohol by novel peripherally and non‐peripherally modular C2‐symmetric diol substituted cobalt (II) phthalocyanines

“…The existence of C N group in the case of phthalonitriles was characterized carbon resonances at around δ = 115.00 ppm. [33] The observation of two carbon resonances at around δ = 115.00 ppm for all the synthesized phthalonitriles in their 13 C NMR spectra is consistent with the general expectation for the structures of 5, 7, 9 and 11. The rest of the aromatic carbons was observed between δ = 105-160 ppm.…”

“…The synthesis of four phthalonitriles among them was reported before in literature. [33,34] The syntheses of new phthalonitriles 5, 7, 9 and 11 were performed by the reaction of 3-nitrophthalonitrile or 4-nitrophthalonitrile with the corresponding phenyl-substituted C 2 symmetric diol in the presence of potassium carbonate in DMSO at room temperature. These reactions gave the desired phthalonitriles 5, 7, 9 and 11 with the yield of around 70%.…”

“…The solubility of phthalocyanine compounds can be improved by incorporation of various substituents to the either non-peripheral or peripheral positions of phthalocyanine skeleton. [1,10,27,28,33,34] We have recently focused on synthesizing of phthalocyanines with bulky C 2 -symmetric diols either peripheral or nonperipheral positions of phthalocyanine skeleton to overcome the solubility and aggregation problems of phthalocyanines. [33,34] The results showed that the phthalocyanines substituted with C 2 -symmteric diols have good solubility in common organic solvents such as diethyl ether, chloroform, dichloromethane, tetrahydrofuran, acetonitrile etc.…”

“…[1,38] Very recently, we reported two cobalt (II) phthalocyanine complexes having both nonsubstituted hydrobenzoin moieties at the peripheral (16) and non-peripheral (20) positions and the catalytic activity of these complexes for the selective oxidation of benzyl alcohol to benzaldehyde were studied in detail. [33] For this purpose, we made a conscious effort to optimize the selective oxidation process of benzyl alcohol and the efficiency of several oxidants (tertiary butyl hydroperoxide; TBHP, m-chloroperoxybenzoic acid; m-CPBA, and hydrogen peroxide; H 2 O 2 ), solvents (dimethylformamide; DMF and acetonitrile; ACN), reaction temperature (25 and 80 C) and the effect of using an additive (potassium bromide; KBr, N-bromosuccinimide; NBS and tetrabutylammonium bromide; Bu 4 NBr) on the catalyst activity was explored for 5 hours of the reaction. We found that the reaction gave the best conversion (94%) and benzaldehyde selectivity (82%) for both nonsubstituted catalysts (16 and 20) in the presence of the catalytic amount of NBS as an additive with TBHP as the source of oxidant in ACN solvent at 80 C. It should also be noted that no oxidation product was observed in the blank experiment which was carried out in the absence of any catalyst under optimized conditions.…”

Peripherally 1,2-dinaphthyl ethanediol substituted phthalocyanine complexes:synthesis, characterization, aggregation, and application in benzyl alcoholoxidation at room temperature

“…The solubility of Pc compounds can be improved by incorporation of various substituents to either the nonperipheral or peripheral positions of the Pc skeleton. This appropriation is one of the most used synthetic strategies to obtain highly soluble and nonaggregated Pc metal complexes [10][11][12][13][14][15][16][17][18].…”