Synthesis, photophysical and electrochemical properties of novel hexadeca-substituted phthalocyanines bearing naphthoxy groups

Kurt, Özge; Özçeşmeci, İbrahim; Koca, Atıf; Gül, Ahmet; Koçak, Makbule Burkut

doi:10.1016/j.dyepig.2016.10.014

Cited by 23 publications

(21 citation statements)

References 40 publications

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“…From the results of the experiment, it is clearly seen from Figure 2 that the absorption intensity of the main Q band of 3 and 4 increased by increasing the concentration of the solution containing Pc compounds. These results confirmed that there were no new bands blue-shifted due to the presence of aggregated species for Pc compounds 3 and 4 [29].…”

Section: Scheme Syntheses Of Phthalonitrile Derivative 2 and Metallosupporting

confidence: 78%

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

Gök¹,

Yılmaz²

2019

Turk J Chem

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In this study, the synthesis of a novel 1,2-dinaphthyl ethanediol substituted phthalonitrile (2) together with tetra-substituted zinc(II) phthalocyanine (Pc) (3) and cobalt(II) Pc (4) bearing 1,2-dinaphthyl ethanediol at peripheral positions was described. The aggregation behaviors of metallophthalocyanines 3 and 4 in solution were investigated by carrying out Beer-Lambert experiments at different concentrations. In addition, the catalytic activity of new cobalt(II) Pc 4 was investigated for benzyl alcohol oxidation. Benzyl alcohol was converted to benzaldehyde using cobalt(II) Pc 4 as a catalyst by a conversion of 99% with selectivity of 100% at room temperature in 1 h. Several spectroscopic techniques such as FT-IR, UV-Vis, 1 H and 13 C NMR, and MALDI-TOF MS were used for the characterization of the newly synthesized compounds.

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Section: Scheme Syntheses Of Phthalonitrile Derivative 2 and Metallosupporting

confidence: 78%

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

Gök¹,

Yılmaz²

2019

Turk J Chem

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“…In these studies, long alkyl chains, such as butoxy or hexyloxy, are attached to the non-peripheral positions of phthalocyanines to improve their solubility. Furthermore, if α-positions of Pcs were substituted with alkoxy substituents, a red-shifted Q band from 650 nm to 750 nm was observed, reducing the highest occupied molecular orbital/lowest unoccupied molecular orbital (HOMO-LUMO) gap [7,19,[22][23][24][25][26][27][28]. With respect to Kobayashi's papers from 2011 and 2014, non-peripherally S-, Se-, or Te-substituted Pcs exhibited Q bands beyond 1000 nm [29,30].…”

Section: Introductionmentioning

confidence: 90%

α- and β-Substituted Metal-Free Phthalocyanines: Synthesis, Photophysical and Electrochemical Properties

Karaoğlu

Burat

2020

Molecules

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Two novel phthalonitrile derivatives, bearing two hexyloxy groups and a benzodioxin (or a naphthodioxin) annulated ring, along with their corresponding metal-free phthalocyanines (H2Pc) were prepared. FT-IR, mass, electronic absorption, 1H NMR, and 13C NMR spectroscopy were employed for the characterization of all compounds. The effect of hexadeca substituents on the photophysical properties of metal-free Pcs was investigated. Photophysical properties of H2Pc were studied in tetrahydrofuran (THF). Fluorescent quantum yields of phthalocyanines (Pcs) were calculated and compared with the unsubstituted phthalocyanine. 1,4-Benzoquinone effectively quenched the fluorescence of these compounds in THF. Cyclic and square wave voltammetry methods were applied to metal-free phthalocyanines and Pc-centered oxidation and reduction processes were obtained.

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“…Therefore, one of the most important purposes of phthalocyanine chemistry is to increase their solubility in different polar and apolar organic solvents. The solubility of phthalocyanines can be improved by adding various substituents such as long alkyn chain or bulky groups to the peripheral, non‐peripheral and axial positions of the molecule, since these substituents increase the space between the stacked phthalocyanine rings . The nature and size of the substituents in the phthalocyanines solubility are not the only criteria; it is also important that the substituents alter the symmetries of the phthalocyanine molecules.…”

Section: Introductionmentioning

confidence: 99%

“…The solubility of phthalocyanines can be improved by adding various substituents such as long alkyn chain or bulky groups to the peripheral, non-peripheral and axial positions of the molecule, since these substituents increase the space between the stacked phthalocyanine rings. [13,14] The nature and size of the substituents in the phthalocyanines solubility are not the only criteria; it is also important that the substituents alter the symmetries of the phthalocyanine molecules. Generally, tetra-substituted phthalocyanines are more soluble than octa-substituted phthalocyanines containing the same groups, owning to the formation of four positional isomers and the high dipole moment resulting from the non-symmetrical arrangement of the substituents on the periphery or non-periphery.…”

Section: Introductionmentioning

confidence: 99%

Investigation of Time‐Kill Evaluation and Antioxidant Activities of New Tetra‐Substituted Metallophthalocyanines Bearing 4‐(Trifluoromethoxy)thiophenyl Groups

et al. 2020

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In the present work, a new phthalonitrile derivative bearing 4‐(trifluoromethoxy)‐thiophenyl group at the 4‐position (2) has been synthesized. Cyclotetramerization of 4‐[4‐(trifluoromethoxy)‐thiophenyl] phthalonitrile (2) in appropriate high‐boiling solvents gave the desired peripherally tetra‐substituted zinc ({2(3),9(10),16(17),23(24)‐tetrakis‐[4‐(trifluoromethoxy)‐thiophenyl]‐phthalocyaninato} zinc(II) (3)) and cobalt phthalocyanines ({2(3),9(10),16(17),23(24)‐tetrakis‐[4‐(trifluoromethoxy)‐ thiophenyl]‐phthalocyaninato} cobalt(II) (4)). The resulting phthalonitrile and phthalocyanine derivatives were characterized by the 1H NMR, 13C NMR, 19F NMR, elemental analysis, UV‐Vis, FT‐IR and mass spectrometric methods. Aggregation properties of macrocycle 3 were investigated in the different concentrations and various solvents. The biological activities of the newly synthesized compounds were investigated by using well diffusion and growth curve kinetic assay. In both methods, the molecules exhibited inhibition effect only on gram negative bacteria. According to the results; molecule 4 showed the highest inhibition activity at both tested concentrations. Antioxidant activities were also evaluated by using 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) and reducing power assays and the molecules performed moderate antioxidant activity.

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Synthesis, photophysical and electrochemical properties of novel hexadeca-substituted phthalocyanines bearing naphthoxy groups

Cited by 23 publications

References 40 publications

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

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

α- and β-Substituted Metal-Free Phthalocyanines: Synthesis, Photophysical and Electrochemical Properties

Investigation of Time‐Kill Evaluation and Antioxidant Activities of New Tetra‐Substituted Metallophthalocyanines Bearing 4‐(Trifluoromethoxy)thiophenyl Groups

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