Ionic porous organic polymer (IPOP) based on twisted biphenyl Scaffold: Green and efficient heterogeneous catalytic synthesis of β-Arylthioketones and biscoumarins

Yadav, Chetna; Payra, Soumen; Moorthy, Jarugu Narasimha

doi:10.1016/j.jcat.2022.07.012

Cited by 11 publications

(13 citation statements)

References 77 publications

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“…All the derivatives were attained by simple filtration of the resultant reaction mixture, followed by hexane wash, and drying under a vacuum afforded 7 a-7 x. Later, the formed products were characterized by 1 H NMR, 13 C NMR, and FT-IR and were confirmed identical to previous literature reports.…”

Section: Resultssupporting

confidence: 77%

“…The concentration of the cumulative filtrates, followed by dichloromethane and ether wash, furnished the desired 1,3-bis(carboxymethyl)imidazolium chloride [BCMIM][Cl] ionic liquid 4 as a white solid with 95% yield. The formed product was further characterized by 1 H, 13 C NMR and FT-IR spectral techniques.…”

Section: Resultsmentioning

confidence: 99%

“…In conclusion, we have demonstrated a novel methodology for the synthesis of bis-coumarins 7 a-7 x by employing 5 mol% [BCMIM][Cl] 4 ionic liquid in aqueous ethanol (1 : 1 v:v 5 mL) at room temperature. A series of 24 derivatives were obtained in good to excellent yields and characterized using 1 H-NMR, 13 C-NMR, and FT-IR spectral techniques. The notable features of this strategy are environmentally benign reaction conditions, an easy-workup procedure by simple filtration, metal-free synthesis, short reaction time, and a low catalyst loading mole percentage.…”

Section: Discussionmentioning

confidence: 99%

“…Bis‐coumarin synthesis involves a Knoevenagel‐Michael addition, which is vital for generating C−C bonds in synthetic organic chemistry. A detailed review of the literature discloses the utilisation of numerous catalysts such as viologen‐based ionic porous organic polymer, [13] Amberlyst 15, [14] nanocatalysts, [15] Mohr's Salt, [16] ionic liquids, [15c,17] Aegle marmelos fruit ash, [18] carbon‐based acid catalyst, [2a] thiamine hydrochloride, [19] biosurfactants, [20] Meglumine, [21] trityl bromide, [22] Phosphotungstic acids, [23] melamine, [24] deep eutectic solvents (DES), [25] choline hydroxide, [26] and so on for the synthesis of biscoumarin. Although most of the stated methods are useful, yet holds several drawbacks, such as critical reaction conditions, expensive catalyst preparation process, low yields, longer reaction durations, and complex work‐up procedures.…”

Section: Introductionmentioning

confidence: 99%

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Facile Synthesis of Bis‐Coumarins Using [BCMIM][Cl] Zwitter Ionic Liquid and Their Binding with Bovine Serum Albumin

et al. 2023

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Herein, we report a novel synthetic pathway for synthesizing bis‐coumarins using 5 mol% [BCMIM][Cl] ionic liquid via the facile, one‐pot, metal‐free synthesis in aqueous ethanol at room temperature. A series of 24 derivatives were furnished in up to 94% yields in 15 min to 1.5 h and were characterized using different spectroscopic techniques. The photophysical properties of bis‐coumarin derivatives were explored through UV‐Visible and fluorescence spectroscopy. The absorption and emission spectra demonstrate a peak wavelength (λmax), within the range of 297–311 nm and 486–505 nm, respectively. An analogous pattern to the experimental results is seen in density functional calculations. The binding affinities of all the synthesised derivatives with Bovine Serum Albumin (BSA) were determined using AutoDock Vina which exhibited a range from −8.4 to −11.5 kcal mol−1. The computed binding constant (KBSA) by tryptophan (Trp) emission quenching values illustrate strong binding interactions of the selected ligands in the order of 104. The calculated binding affinities were validated by performing molecular dynamics simulations of the best docking pose using GROMACS software over a period of 1 ns for studying the stability of protein‐ligand complexes.

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Section: Resultssupporting

confidence: 77%

Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Facile Synthesis of Bis‐Coumarins Using [BCMIM][Cl] Zwitter Ionic Liquid and Their Binding with Bovine Serum Albumin

et al. 2023

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“…[23][24][25][26] In general, the performances of catalytic materials are controlled by the kind of support employed, the porous structure and physiochemical properties. In our continuing investigations on porous MOFs [27][28][29][30][31] and POPs, [32][33][34] we specifically sought to explore the catalytic performances of POPs endowed with carboxy functionalities. Herein, we report the synthesis of a carboxy-functionalized porous organic polymer, that is, Carboxy-POP, by Friedel-Crafts polyalkylation followed by hydrolysis, and its application for facile catalytic synthesis of biologically-active xanthenes and acridine derivatives.…”

Section: Introductionmentioning

confidence: 99%

Porous Organic Polymer with Free Carboxylic Acids (Carboxy‐POP) for Heterogeneous Catalytic One‐Pot Synthesis of Xanthenes and Acridines

Karn,

Yadav,

Kumar Sahoo

et al. 2023

ChemCatChem

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Porous organic polymers (POPs) – the emergent hydrothermally stable, amorphous and porous materials – have proven to be invaluable for catalytic applications. Through a rational bottom‐up design, we have developed a Carboxy‐POP, a POP that is adorned by Bronsted acid (COOH) functionalities, for heterogeneous catalysis. The Carboxy‐POP has been comprehensively characterized by FT‐IR, solid‐state 13C NMR, SEM, TEM, etc. It exhibits a moderate porosity with a BET surface area of 381 m2 g‐1 and acidic concentration of 1.67 mmol/g. Its functional utility as an efficient heterogeneous catalyst for one‐pot synthesis of a variety of xanthenes and acridines in excellent isolated yields (up to 90%) is demonstrated. In contrast to the conventional methods, the advantages of the reported metal‐free catalytic protocol include ease of operation, excellent isolated yields of the products, facile workup, and shorter reaction times. It is shown that the heterogeneous catalyst can be repetitively used with the catalytic activity almost intact even after 16 reaction cycles.

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Porous Organic Polymers (POPs) Based on Acridone as Heterogeneous Photocatalysts for Oxidative Dimerization and Cyclocondensation Reactions

Tamuly,

Sahoo,

Yadav

et al. 2024

ChemCatChem

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Porous organic polymers (POPs) are emergent tailor‐made materials, which can be accessed by covalent polymerization of diligently designed molecular building blocks in a bottom‐up fashion. Acridone, a well‐known chromophore that undergoes intersystem crossing (ISC) with near‐unity quantum yield akin to benzophenone, was structurally elaborated into a building block and subjected to Friedel‐Crafts polyalkylation to afford a series of POPs, namely, Ac‐MePOP, Ac‐OMePOP, and Ac‐CBPOP. These POPs exhibit remarkable porosity and significant absorption in the visible region. Of the three polymers, Ac‐CBPOP with the highest BET surface area of ca. 1027 m2/g is shown to serve as an excellent heterogeneous photocatalyst for visible light‐mediated oxidative transformations, that is, oxidative coupling of benzylamines to imines and cyclocondensation of o‐phenylenediamines with aldehydes to benzimidazoles under oxygen atmosphere. It is further shown that Ac‐CBPOP can be reused for several reaction cycles without any loss of catalytic activity with its stability intact. Mechanistic studies show that 1O2 serves as the key reactive oxygen species, formed by the energy transfer from Ac‐CBPOP to 3O2, in the photocatalytic oxidation reactions. The results demonstrate the development of stable photocatalytic POP materials with tailor‐made properties by a bottom‐up covalent polymerization of programmed molecular building blocks.

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Ionic porous organic polymer (IPOP) based on twisted biphenyl Scaffold: Green and efficient heterogeneous catalytic synthesis of β-Arylthioketones and biscoumarins

Cited by 11 publications

References 77 publications

Facile Synthesis of Bis‐Coumarins Using [BCMIM][Cl] Zwitter Ionic Liquid and Their Binding with Bovine Serum Albumin

Facile Synthesis of Bis‐Coumarins Using [BCMIM][Cl] Zwitter Ionic Liquid and Their Binding with Bovine Serum Albumin

Porous Organic Polymer with Free Carboxylic Acids (Carboxy‐POP) for Heterogeneous Catalytic One‐Pot Synthesis of Xanthenes and Acridines

Porous Organic Polymers (POPs) Based on Acridone as Heterogeneous Photocatalysts for Oxidative Dimerization and Cyclocondensation Reactions

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