Further insight into aryl nitration of tetraphenylporphyrin

Xue, Zhi; Lee, Priscilla P. S.; Wang, Yanming; Kwong, Daniel W. J.; Li, Jing; Xin, John Haozhong; Wong, Wai Kwok; Cheuk, Kevin Ka Leung

doi:10.1016/j.tet.2011.06.031

Cited by 8 publications

(6 citation statements)

References 36 publications

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“…Porphyrins bearing aryl moieties in meso ‐positions (5, 10, 15, 20) can also be successfully nitrated in these rings. In this case, the only mechanism described in the literature was the electrophilic one [21,88–92,95–101,103] . For the first time, this type of nitration taking place on meso ‐phenyl rings was reported by Kruper et al [88] .…”

Section: Nitration Of Porphyrins In Meso‐aryl Ringsmentioning

confidence: 80%

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Nitration of Porphyrin Systems: A Toolbox of Synthetic Methods

Mikus

Łopuszyńska

2020

Chemistry An Asian Journal

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This review addresses nitration reactions of porphyrin derivatives. Simple porphyrins modifications afford valuable intermediates in this area of chemistry. They are useful materials for further transformations, as the NO2 group introduced into parent porphyrin system increases its electrophilic character, thus allowing a broad spectrum of subsequent reactions, e. g. reduction of NO2 to NH2, subsequent diazotisation, nucleophilic substitution of hydrogen (in ortho‐position to NO2), a variety of cyclizations, etc. Such reactions are often utilized in the first steps of the designed syntheses, leading to attractive and useful target porphyrin molecules. This approach (via nitro‐derivatives) allows synthesizing numerous porphyrin‐like compounds of a high degree of complexity, and has thus become one of the methods choice. The substitution by NO2 group can take place at all positions of the porphyrin systems: four meso‐positions (5, 10, 15, 20) and eight positions β (2, 3, 7, 8, 12, 13, 17, 18). The third possibility includes the nitration in meso‐aryl rings attached to positions 5, 10, 15, and 20. The latter derivatives (meso‐aryl substituted ones) are a large, well‐known group of synthetic porphyrins. The nitration reactions described herein follow three various mechanisms: (a) radical, (b) via π‐cation radicals and π‐dications, and (c) electrophilic. All the above cases are discussed in detail. According to our knowledge, this is the first such systematic account concerning these reactions.

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Section: Nitration Of Porphyrins In Meso‐aryl Ringsmentioning

confidence: 80%

“…In 2011 Xue et al. described the synthesis of moderately soluble 5,10,15,20‐tetrakis( p ‐nitrophenyl)porphyrin ( 100 ) with very good yield (87%) [99] . In this case the red fuming nitric acid was used.…”

Section: Nitration Of Porphyrins In Meso‐aryl Ringsmentioning

confidence: 99%

Nitration of Porphyrin Systems: A Toolbox of Synthetic Methods

Mikus

Łopuszyńska

2020

Chemistry An Asian Journal

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“…All reagents were supplied from commercial source and used without further purification. 5,10,15,20-Tetrakis(4-aminophenyl) porphyrin (TAP) was synthesized by previously reported procedure 44 which is described in Section S1 in the Supporting Information. 1,3,6,8-Tetrakis(4-formylphenyl) pyrene (TFFPy) was synthesized via new synthetic route for better yield.…”

Section: Methodsmentioning

confidence: 99%

Electrochemical Stimuli-Driven Facile Metal-Free Hydrogen Evolution from Pyrene-Porphyrin-Based Crystalline Covalent Organic Framework

Bhunia¹,

Das²,

Jana

et al. 2017

ACS Appl. Mater. Interfaces

202

141

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A [2 + 2] Schiff base type condensation between 5,10,15,20-tetrakis(4-aminophenyl)porphyrin (TAP) and 1,3,6,8-tetrakis (4-formylphenyl) pyrene (TFFPy) under solvothermal condition yields a crystalline, quasi-two-dimensional covalent organic framework (SB-PORPy-COF). The porphyrin and pyrene units are alternatively occupied in the vertex of 3D triclinic crystal having permanent microporosity with moderately high surface area (∼869 m g) and promising chemical stability. The AA stacking of the monolayers give a pyrene bridged conducting channel. SB-PORPy-COF has been exploited for metal free hydrogen production to understand the electrochemical behavior using the imine based docking site in acidic media. SB-PORPy-COF has shown the onset potential of 50 mV and the Tafel slope of 116 mV dec. We expect that the addendum of the imine based COF would not only enrich the structural variety but also help to understand the electrochemical behavior of these class of materials.

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“…Synthesis and functionalization of porphyrins [1] have long been of great interest in the chemistry community because of the vast potentials and demands for porphyrin derivatives in diverse fields, such as materials [2, 3], supramolecular chemistry [4, 5], biomimetic models [6], catalysis [7, 8], photodynamic therapy [9], and ionophores [10]. Porphyrins were reported to exhibit a variety of biological activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectroscopic, and Biological Studies on New Zirconium(IV) Porphyrins with Axial Ligand

Bajju

Devi²,

Katoch³

et al. 2013

Bioinorganic Chemistry and Applications

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A series of parasubstituted tetraphenylporphyrin zirconium(IV) salicylate complexes (SA/5-SSAZr(IV)RTPP, R = p-H, p-CH3, p-NO2, p-Cl, SA = salicylate, and 5-SSA = 5-sulfosalicylate) have been synthesized, and the spectral properties of free base porphyrins, their corresponding metallated, and axially ligated zirconium(IV) porphyrin compounds were compared with each other. A detailed analysis of ultraviolet-visible (UV-vis), proton nulcear magnetic resonance (1H NMR) spectroscopy, infrared (IR) spectroscopy, and elemental analysis suggested the transformation from free base porphyrins to zirconium(IV) porphyrins. The ability of the metal in this complex for extra coordination of solvent molecules was confirmed by ESI-MS spectra. Besides the fluorescence, cyclic voltammetry, and thermogravimetric studies, the complexes were also screened for antimicrobial and anticancer activities. Among all the complexes, 5-SSAZr(p-NO2TPP) shows high antibacterial activity.

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Further insight into aryl nitration of tetraphenylporphyrin

Cited by 8 publications

References 36 publications

Nitration of Porphyrin Systems: A Toolbox of Synthetic Methods

Nitration of Porphyrin Systems: A Toolbox of Synthetic Methods

Electrochemical Stimuli-Driven Facile Metal-Free Hydrogen Evolution from Pyrene-Porphyrin-Based Crystalline Covalent Organic Framework

Synthesis, Spectroscopic, and Biological Studies on New Zirconium(IV) Porphyrins with Axial Ligand

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