<i>meso</i>‐Pyrrole‐Substituted 22‐Oxacorroles: Building Blocks for the Synthesis of BODIPY‐Bridged 22‐Oxacorrole Dyads

Kalita, Hemanta; Ravikanth, Mangalampalli

doi:10.1002/chem.201500702

Cited by 9 publications

(7 citation statements)

References 16 publications

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“…This effect is predominantly observed to be caused by the effect of a Lewis acidic cobalt chloride salt on decomposition. 45 In addition, the minima of endothermic peaks for the decomposition shifts toward lower temperature (from 303 to 260 °C). Thus, in the presence of metal salts, this endoeffect of thermodestruction decreases by 2-fold and occurs at a low temperature.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Dual Role of Deep Eutectic Solvent as a Solvent and Template for the Synthesis of Octahedral Cobalt Vanadate for an Oxygen Evolution Reaction

Thorat

Jadhav

Roy

et al. 2018

ACS Sustainable Chem. Eng.

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In this study, the deep eutectic solvent (DES)-aided synthesis of γ-CoV 2 O 6 under modest reaction conditions using 1:1 choline chloride−malonic acid was reported. In the presence of DES, the reaction occurred at a lower temperature (500 °C) compared with that of the respective conventional solid-state synthesis of metal oxides and also with the calcination process involving the metal salts, thereby decreasing the overall formation energy. Differential scanning calorimetry revealed a 2-fold decrease in the endo effect of the thermodestruction of DES, which was observed at a low temperature. The structural pathway taken during the phase and morphology formation was investigated by in situ and ex situ X-ray diffraction (XRD) analysis, Raman spectroscopy, and scanning electron microscopy. The in situ XRD results confirmed the presence of high-temperature α-CoV 2 O 6 , which was finally converted to γ-CoV 2 O 6 . On account of the metal speciation in DES similar to the biotemplate, well-defined octahedral CoV 2 O 6 nanocrystals were obtained, which exhibited a remarkable OER catalytic activity at current density of 10 mA/cm 2 with an overpotential of a mere 324 mV, with excellent durability for greater than 24 h. Thus, a designer DES solvent with characteristics of biodegradability, cost-effectiveness, and renewability demonstrates potential for the synthesis of noble-metal-free oxygen evolution reaction (OER) catalysts, which allows the present synthesis route to fit well within the merits of green chemistry.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Dual Role of Deep Eutectic Solvent as a Solvent and Template for the Synthesis of Octahedral Cobalt Vanadate for an Oxygen Evolution Reaction

Thorat

Jadhav

Roy

et al. 2018

ACS Sustainable Chem. Eng.

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“…The iron corroles containing halogen axial ligand 48-51 showed porphyrinoid like absorption features such as intense Soret band and several minor Q-bands. Most of these iron corroles (48-50, 52-54) displayed elongated Fe-axial ligand and short equatorial Fe- (35)(36)(37) to understand macrocycle's adaptability towards metal ions of different sizes while forming complexes. The synthesis of Ni, Cu, and Pd derivatives of these corroles is shown in Scheme 15.…”

Section: -Azacorrolesmentioning

confidence: 99%

“…Kalita and Ravikanth further extended this synthetic strategy to prepare meso-free mono-meso-pyrrolyl 22-oxacorroles 101, 102 as shown in Scheme 25. 35 Chandrashekar and co-workers 36 obtained meso-ferrocenyl 22-oxacorroles 113-117 as minor products ($3% yield) along with meso-ferrocenyl 25-oxasmaragdyrins 108-112 ($20% yield) by condensing appropriate 16-oxatripyrranes 88, 104-107 with meso-ferrocenyl dipyrromethane 103 under TFA-catalyzed conditions (Scheme 26).…”

Section: -Oxacorrolesmentioning

confidence: 99%

“…Kalita and Ravikanth further extended this synthetic strategy to prepare meso -free mono- meso -pyrrolyl 22-oxacorroles 101, 102 as shown in Scheme 25 . 35 …”

Section: Corroles Containing Heteroatom(s) At Their Core (Core Modifi...mentioning

confidence: 99%

“…Kalita and Ravikanth 35 reported the synthesis of novel boron-dipyrromethene (BODIPY)-bridged 22-oxacorrole dyads 132, 133 by using meso -pyrrolyl 22-oxacorrole 101 as a key synthon as shown in Scheme 30 . The BODIPY-bridged corrole dyads 132, 133 showed an absorption band at 520 nm due to the BODIPY moiety and three bands at 399, 572 and 618 nm due to corrole units ( Fig.…”

Section: Corroles Containing Heteroatom(s) At Their Core (Core Modifi...mentioning

confidence: 99%

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Heterocorroles: corrole analogues containing heteroatom(s) in the core or at a meso-position

2018

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One‐Pot Preparation of Non‐Symmetric meso‐Aryl‐BODIPYs: Functional Derivatives with Unusual Reactivity

et al. 2016

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The formation of meso‐aryl‐BODIPYs (boron dipyrrins) through the acidic condensation of 3,4‐dialkylpyrroles with aromatic aldehydes, followed by 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) oxidation and BF2 complexation, has been reviewed. Surprisingly, it was found that the major products from these reactions were not the anticipated symmetric BODIPYs, but non‐symmetric derivatives carrying one benzyl substituent at the BODIPY α position. The best yields and simple purification conditions were be achieved if the oxidant was not employed in the one‐pot reaction sequence. Electron‐rich benzaldehydes provided the best results, whereas precursors with electron‐withdrawing substituents gave significant amounts of the symmetric BODIPYs as side‐products. This unexpected result can be rationalized mechanistically on the basis of two reaction pathways that diverge from a common intermediate at an early step in the condensation sequence. Preliminary reactivity investigations showed chlorination to give unexpected results, but a typical substitution and coupling chemistry.

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meso‐Pyrrole‐Substituted 22‐Oxacorroles: Building Blocks for the Synthesis of BODIPY‐Bridged 22‐Oxacorrole Dyads

Cited by 9 publications

References 16 publications

Dual Role of Deep Eutectic Solvent as a Solvent and Template for the Synthesis of Octahedral Cobalt Vanadate for an Oxygen Evolution Reaction

Dual Role of Deep Eutectic Solvent as a Solvent and Template for the Synthesis of Octahedral Cobalt Vanadate for an Oxygen Evolution Reaction

Heterocorroles: corrole analogues containing heteroatom(s) in the core or at a meso-position

One‐Pot Preparation of Non‐Symmetric meso‐Aryl‐BODIPYs: Functional Derivatives with Unusual Reactivity

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