Corroles in 1,3-dipolar cycloaddition reactions

Vale, Luís S.H.P.; Barata, Joana F. B.; Santos, Carla I. M.; Neves, Maria G. P. M. S.; Faustino, Maria A. F.; Tomé, Augusto C.; Silva, Artur M. S.; Paz, Filipe A. A.; Cavaleiro, José A. S.

doi:10.1142/s1088424609000371

Cited by 29 publications

(20 citation statements)

References 31 publications

(43 reference statements)

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“…[3] A particular type of corrole modification through the pyrrolic units involves cycloaddition reactions. [5] Only a few groups have reported post-macrocyclization elaborations by means of the meso positions of the contracted porphyrin framework.…”

Section: Introductionmentioning

confidence: 99%

Synthetic, Structural, and Photophysical Exploration of meso‐Pyrimidinyl‐Substituted AB₂‐Corroles

Ngo

Puntoriero²,

Nastasi³

et al. 2010

Chemistry A European J

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meso-Pyrimidinyl-substituted AB(2)-corroles were efficiently synthesized starting from 5-mesityldipyrromethane and various 2-substituted 4,6-dichloropyrimidine-5-carbaldehydes. The corrole yield was significantly enhanced by optimization of the amount of Lewis acid catalyst (BF(3).OEt(2)). The main advantage of pyrimidinylcorroles over other meso-triarylcorroles is their wide range of functionalization possibilities, which has been explored by nucleophilic and electrophilic aromatic substitution, and Pd-catalyzed cross-coupling reactions. Stepwise substitution of the chlorine functions afforded asymmetrically substituted pyrimidinylcorroles. Due to the lability of the free-base corrole macrocycles, functionalization of the corrole periphery was preferentially performed on the Cu-metalated counterparts. Functionalized free-base AB(2)-pyrimidinylcorroles were, however, readily accessible by the reversible sequence Cu insertion and subsequent reductive demetalation. AB(2)-pyrimidinylcorroles can hence be regarded as highly versatile platforms towards more sophisticated corrole systems. X-ray analysis of a bis(4-tert-butylphenoxy)-substituted Cu-pyrimidinylcorrole showed the typical features of a Cu-corrole: short N-Cu distances and a saddled corrole plane. The absorption spectra and photophysical properties of some representative free-base AB(2)-pyrimidinylcorroles were examined in depth. The absorption spectra displayed typical corrole features: intense spin-allowed pi-pi* bands, which can be classified as Soret- and Q-type bands. The photophysical properties, investigated both in fluid solution at room temperature and in rigid matrix at 77 K, were governed by the lowest-lying pi-pi* singlet state; however, in most cases, a state with partial charge-transfer character (from the corrole ring to the pyrimidinyl group) was proposed to contribute to the dynamic properties of the emissive level.

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Section: Introductionmentioning

confidence: 99%

Synthetic, Structural, and Photophysical Exploration of meso‐Pyrimidinyl‐Substituted AB₂‐Corroles

Ngo

Puntoriero²,

Nastasi³

et al. 2010

Chemistry A European J

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“…Moreover, the efficiency of the Vilsmeier-Haack reaction is well established, giving access to functionalized species in excellent yields. [20][21][22] We present in this work details of the efficiency of this reaction coupled with the subsequent Knoevenagel condensation, to obtain corrole derivatives functionalized with grafting substituents. This synthetic pathway provides an effective monodentate anchoring group and increases the distance of the corrole macrocycle from the metal surface.…”

Section: Introductionmentioning

confidence: 99%

Grafting Copper and Gallium Corroles onto Zinc Oxide Nanoparticles

et al. 2019

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Two different copper and gallium arylcorroles have been functionalized using the Vilsmeier–Haack reaction. A further Knoevenagel reaction with cyanoacetic acid was performed on both complexes, affording the desired products with yields above 90 %. The newly synthesized compounds have been thoroughly characterized by a combination of spectroscopic methods, optical analyses, and X‐ray crystallography. Moreover, they have been tested as anchoring groups for the hydrothermal synthesis of ZnO nanoparticles. The morphology of the heterogeneous composites has been studied by SEM, EDS and fluorescence microscopy analyses, thus confirming the presence of the corrole macrocycle in the hybrid material.

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“…39,40,[43][44][45] Nowadays, its functionalization and further applications as catalysts, dyes for solar energy conversion and in medicine are attracting increasing interest. 39,43,46,47 However, up to date, there are no reports on using Corroles to modify Fe 3 O 4 magnetic nanoparticles, which can be employed as colorimetric sensing materials to detect H 2 O 2 and glucose.…”

Section: Introductionmentioning

confidence: 99%

Corrole functionalized iron oxide nanocomposites as enhanced peroxidase mimic and their application in H2O2 and glucose colorimetric sensing

Gao¹,

Zhang²,

Lyu³

et al. 2018

Eng. Sci.

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For the first time, functional Corrole molecules modified iron oxide (Fe 3 O 4) magnetic nanoparticles (MNPs) were prepared by a facile two-step method. The Corrole-Fe 3 O 4 nanocomposites exhibited a higher peroxidase-like activity than that of pure Fe 3 O 4 nanoparticles, and accelerated the oxidation of peroxidase substrate 3,3',5,5'-tetramethylbenzidine (TMB) with the help of hydrogen peroxide (H 2 O 2) only in 5 min, attributing to hydroxyl radicals (•OH) generated in the process of oxidation of TMB. Kinetic analysis showed that the catalytic behaviors followed the typical Michaelis-Menten kinetics. Additionally, Corrole-Fe 3 O 4 exhibits several advantages including low cost, easy separation, facile fabrication, and high catalytic efficiency. Based on the catalytic activity of Corrole-Fe 3 O 4 nanocomposites, a simple, sensitive, and selective colorimetric biosensor for H 2 O 2 and glucose determination was successfully designed. The linear relationships of absorbance of oxidized TMB at 652 nm with H 2 O 2 or glucose concentration were obtained from 10 μM to 100 μM with a detection limit of 3.6 μM and 4 μM to 40 μM with the detection limit as low as 2.46 μM, respectively. The results demonstrate that the Corrole-Fe 3 O 4 nanocomposites have potential applications in bioanalysis and biodetection.

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Corroles in 1,3-dipolar cycloaddition reactions

Cited by 29 publications

References 31 publications

Synthetic, Structural, and Photophysical Exploration of meso‐Pyrimidinyl‐Substituted AB₂‐Corroles

Synthetic, Structural, and Photophysical Exploration of meso‐Pyrimidinyl‐Substituted AB₂‐Corroles

Grafting Copper and Gallium Corroles onto Zinc Oxide Nanoparticles

Corrole functionalized iron oxide nanocomposites as enhanced peroxidase mimic and their application in H2O2 and glucose colorimetric sensing

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Corroles in 1,3-dipolar cycloaddition reactions

Cited by 29 publications

References 31 publications

Synthetic, Structural, and Photophysical Exploration of meso‐Pyrimidinyl‐Substituted AB2‐Corroles

Synthetic, Structural, and Photophysical Exploration of meso‐Pyrimidinyl‐Substituted AB2‐Corroles

Grafting Copper and Gallium Corroles onto Zinc Oxide Nanoparticles

Corrole functionalized iron oxide nanocomposites as enhanced peroxidase mimic and their application in H2O2 and glucose colorimetric sensing

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Synthetic, Structural, and Photophysical Exploration of meso‐Pyrimidinyl‐Substituted AB₂‐Corroles

Synthetic, Structural, and Photophysical Exploration of meso‐Pyrimidinyl‐Substituted AB₂‐Corroles