Synthesis and characterization of three covalently linked porphyrin-phthalocyanine pentamers with nucleophilic substitution

Osati, Samira; Safari, Nasser; Jamaat, Parisa Rajabali

doi:10.1016/j.ica.2010.03.022

Cited by 18 publications

(7 citation statements)

References 27 publications

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“…The synthetic route of H 2 TeCPp used in our study was the well-known Adler–Longo method: propionic acid (150 mL) was refluxed together with methyl 4-formylbenzoate (6.0 g, 36 mmol) at 140 °C, and excess distilled pyrrole (2.5 mL, 36 mmol) in propionic acid (12.5 mL) was added dropwise in 30 min. Then the mixture was stirred with a magnetic stirrer bar for another 1 h. Evaporation of the solvent gave a crude product after cooling to room temperature and adding EtOH (20 mL).…”

Section: Methodsmentioning

confidence: 99%

“…Tetrakis(4-carboxyphenyl)porphyrin (H 2 TeCPp). The synthetic route of H 2 TeCPp used in our study was the well-known Adler− Longo method: 51 propionic acid (150 mL) was refluxed together with methyl 4-formylbenzoate (6.0 g, 36 mmol) at 140 °C, and excess S1a, Table S1 entry In a typical synthesis route as above, methyl 4-formylbenzoate (4.5 g, 27 mmol) and benzaldehyde (1.0 mL, 9 mmol) were dissolved in a certain ratio with 150 mL of propionic acid. Then the mixture was heated to reflux at 140 °C, and freshly distilled pyrrole (2.5 mL, 36 mmol) in propionic acid (12.5 mL) was added to the solution dropwise in 30 min.…”

Section: Introductionmentioning

confidence: 99%

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Synthetic Methodology for the Fabrication of Porous Porphyrin Materials with Metal–Organic–Polymer Aerogels

et al. 2016

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A promising fabrication strategy used for designing porous porphyrin materials and a group of rigid carboxyl porphyrins based metal-organic-polymer aerogels (MOPAs) has been proposed recently. These newly synthesized MOPAs were exemplarily characterized by FT-IR, UV-vis-DRS, EDS, PXRD, TGA, SEM, TEM, and gas sorption measurements. A gelation study has shown that solvents, molar ratio, temperature, and peripheral carboxyl number in porphyrins all affect gel generation. The MOPA series exhibit eminent thermal stability, high removal efficiency in dye adsorption, versatile morphologies, and permanent tunable porosity; also the BET surface areas fall within the range 249-779 m(2) g(-1). All of the mentioned properties are significantly superior to some other porous materials, which enable these compounds to be potential candidates for dye uptake, gas storage, and separation.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthetic Methodology for the Fabrication of Porous Porphyrin Materials with Metal–Organic–Polymer Aerogels

et al. 2016

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“…The mixture was cooled overnight and filtered off under vacuum. Purification was done by column chromatography (silica-gel) using dichloromethane as eluant, the purple solid of compound 1 (1.2 g) was obtained in the yield of 4.9 per cent, mp > 300°C; 1 H NMR (500 MHz, CDCl 3 , d /ppm): -2.77 (s, 2H, pyrrole), 7.15 (d, J = 8.0 Hz, 2H, Ph), 7.73-7.77 (m, 9H, Ph), 8.06 (d, J = 8.0 Hz, 2H, Ph), 8.20-8.22 (m, 6H, Ph), 8.84-8.87 (m, 8H, pyrrole) (Osati et al, 2010;Sun et al, 2006;Tomé et al, 2005).…”

Section: Expermentalmentioning

confidence: 99%

Synthesis of novel zinc porphyrins and their photocatalytic activity

Chen

2018

PRT

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Purpose The purpose of this study is to investigate the effect of the spacer length of zinc porphyrin-TiO2 hybrids by photodegradation of methyl orange (MO) in aqueous solution under visible light. Design/methodology/approach 5-Mono-[4-hydroxyphenyl]-10,15,20-triphenylporphyrin was synthesized using Alder method. A new series of porphyrins and their corresponding zinc complexes (ZnPp) were obtained from 5-mono-[4-hydroxyphenyl]-10,15,20-triphenylporphyrin via nucleophilic substitution reaction. The ZnPp-TiO2 photocatalysts were prepared by loading ZnPp onto TiO2 and characterized by scanning electron microscope, X-ray diffraction, UV-vis diffuse reflectance spectrum and X-ray photoelectron spectroscopy. Findings The results indicated that zinc porphyrins were successfully loaded on the surface of TiO2 microsphere, which is crucial to enhance the activity of the catalytic composite under visible light. All the novel photocatalysts showed much enhanced photoactivity than bare TiO2. Among all the prepared ZnPp-TiO2, 5,10,15-triphenyl-20-[4-(4-naphthoxy)-butoxy]phenyl zinc porphyrin-TiO2 (4b) showed the highest photocatalytic activity for the degradation of MO. Research limitations/implications Synthesis of these zinc porphyrins had never been reported previously. Originality/value Four novel zinc porphyrin-TiO2 photocatalysts which could response to visible light in degradation of MO were synthesized using Alder method. The results show that the photocatalytic activity of 5,10,15-triphenyl-20-[4-(4-naphthoxy)butoxy] phenyl zinc porphyrin- TiO2 is higher than others.

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“…The synthetic method used in our study was the well-known Adler-Longo method . 4-(4-Formylphenoxy)ethylbenzoate (12 mmol) and pyrrole (12 mmol) were reacted in refluxing propionic acid for 50 min.…”

Section: Methodsmentioning

confidence: 99%

Permanently Porous Co(II) Porphyrin-Based Hydrogen Bonded Framework for Gas Adsorption and Catalysis

Zhang

Yao

et al. 2015

Crystal Growth & Design

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A new microporous hydrogen-bonded organic framework (HOF) based on a cobalt(II) porphyrin, namely, Co(II) 5,10,15,20-tetra(4-(4-acetateethyl)phenoxy)phenylporphyrin (1), has been synthesized and structurally characterized. Single crystal X-ray diffraction analysis reveals that porphyrin molecules connect each other by intermolecular hydrogen bonds to form 2D layer, and the 2D layer further links though π···π interactions to form 3D supramolecular structure, exhibiting one kind of micropore with 3.98 × 6.47 Å2. The HOF of 1 exhibits not only a permanent porosity with the Langmuir surface areas of 158.79 m2·g–1, and the Brunauer–Emmett–Teller surface areas of 97.70 m2·g–1, but also, more importantly, high catalytic efficiency and selectivity for oxidation of ethylbenzene to acetophenone in quantitative 83.1% yield.

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Synthesis and characterization of three covalently linked porphyrin-phthalocyanine pentamers with nucleophilic substitution

Cited by 18 publications

References 27 publications

Synthetic Methodology for the Fabrication of Porous Porphyrin Materials with Metal–Organic–Polymer Aerogels

Synthetic Methodology for the Fabrication of Porous Porphyrin Materials with Metal–Organic–Polymer Aerogels

Synthesis of novel zinc porphyrins and their photocatalytic activity

Permanently Porous Co(II) Porphyrin-Based Hydrogen Bonded Framework for Gas Adsorption and Catalysis

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