Synthesis of novel coumarin containing conjugated fluorescent polymers by Suzuki cross-coupling reactions and their chemosensing studies for iron and mercury ions

Bhaumick, Prabhas; Jana, Asim Kumar; Choudhury, Lokman H.

doi:10.1016/j.polymer.2021.123415

Cited by 14 publications

(9 citation statements)

References 56 publications

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“…This indicates the occurrence of Hg(II)-induced deprotection of dithioacetal SC62, and an aldehyde 99 was formed on the addition of Hg 2 + (Scheme 78). While SC63 also undergoes the same reaction mechanism as SC62 on adding Hg 2 + enhancing the fluorescence by 340-folds with LOD of 9.0 × 10 À 8 M. It can successfully sense Hg 2 + ions in HeLa cells with the help of fluorescent ratiometric techniques Bhaumick et al synthesized a conjugated coumarin-containing fluorescent co-polymer SC64 [123] from monomer 101 with Pd catalyzed Suzuki-Miyaura cross-coupling reaction where benzene-1, 4-diboronic acid was replaced with 9, 9-dioctylfluorene-2,7-diboronic acid (Scheme 79). The polymer SC64 displayed similar absorption at 345 nm in different solvents i. e., dimethyl sulfoxide (DMSO), dimethyl formamide (DMF), chloroform (CHCl 3 ), and tetrahydrofuran (THF).…”

Section: Mercury Ions (Hg 2 + )mentioning

confidence: 99%

“…Synthetic route of polymer SC64. [123] nisms for processing transition metals include neurological diseases, Alzheimer's and Parkinson's, anemia, and hemochromatosis.…”

Section: Coumarin Derivatives As Chemosensors For Transition Metal Ionsmentioning

confidence: 99%

“…[ [104][105][106][107][108][109][110][111][112][113][114][115][116][117][118][119][120][121][122][123] 9.…”

Section: Sc37-sc64unclassified

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Coumarin‐based Chemosensors for Metal Ions Detection

et al. 2022

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Coumarins, due to their intense and persistent emission of fluorescence, structural flexibility, and excellent biocompatibility, have become a popular choice in developing new fluorescent chemosensors. Coumarins have long been used for sensing anions, cations, chemically reactive nitrogen, oxygen, sulfur-containing species, and small molecules. They have also been shown to have applicability in imaging, biology, and medical research. Due to the widespread use and excellent biological activity, hundreds of such coumarin motifs have either been isolated from nature or synthesized in a laboratory. This review covers all the developments pertaining to the synthesis and use of coumarin for sensing a variety of metal ions (alkali, alkaline earth, transition, heavy, and noble metal ions). This comprehensive review includes an overview of the coumarin-based chemosensor's pH limit, detection limit, and binding mode. A brief explanation of the stoichiometric ratio between metal and chemosensor moiety and the applicability of each chemosensor is also given.

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Section: Mercury Ions (Hg 2 + )mentioning

confidence: 99%

“…Synthetic route of polymer SC64. [123] nisms for processing transition metals include neurological diseases, Alzheimer's and Parkinson's, anemia, and hemochromatosis.…”

Section: Coumarin Derivatives As Chemosensors For Transition Metal Ionsmentioning

confidence: 99%

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Coumarin‐based Chemosensors for Metal Ions Detection

et al. 2022

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“…Conjugated polymers (CPs) with a conjugated long π-electron in their backbone system enable charges to effectively transport the polymer backbones. , They have been widely utilized in conductors, energy stores, and sensors. − Recently, compared with the monomers or other traditional small molecules, CP-based fluorescent sensors have drawn considerable interest in the field of biosensors owing to their unique and effective “molecular wire effect” properties. , Meanwhile, this kind of fluorescent sensor shows excellent capabilities in light-harvesting and signal amplifying, which closely impacts its final properties and applications . Generally, the photochemical properties of these sensors are dependent on repeating units .…”

Section: Introductionmentioning

confidence: 99%

Amino Acid Groups Enable Electrosynthesized Polyfluorenes to Specifically Recognize Cr₂O₇^2–

Zhang

Zou

et al. 2022

ACS Appl. Polym. Mater.

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The unique “molecular wire effect” property of conjugated polymers (CPs) enables them to own signal amplification. Therefore, they are good candidates for constructing fluorescent sensors with high sensitivity. In this work, two water-soluble polyfluorene derivatives P(Fmoc-Arg-OH) and P(Fmoc-Glu-OH) were synthesized using electrochemical polymerization in boron trifluoride diethyl etherate–trifluoroacetic systems. Absorption and emission spectra showed that the two polymers were blue emitters. In order to specifically target dichromate ions (Cr2O7 2–), we introduced amino acid groups in the side chain of the two polymers. A series of selective and competitive experiments in a pH = 7.00 PBS solution showed that both polymers had high selectivity toward Cr2O7 2–. Thanks to their signal amplification effect, the limits of detection of P(Fmoc-Arg-OH) and P(Fmoc-Glu-OH) could reach 16.67 pM and 3.33 μM, respectively. All results showed that CPs are a good platform for designing fluorescent sensors with high selectivity and sensitivity.

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“…The synthesis of substituted coumarins is still dominated by classical methods, such as the Knoevenagel, Perkin, and Pechmann reactions [ 12 , 13 , 14 ], which although powerful and proven, have limited scope in terms of functional group compatibility. Recent studies have centered on the use of palladium-catalyzed cross-coupling C–C bond formation leading to the 3-, 4- and 6-substituted coumarins [ 15 , 16 , 17 , 18 , 19 ]; thus the number of Pd-catalyzed approaches for obtaining coumarins is constantly growing [ 20 , 21 , 22 ]. However, most of these synthetic protocols are focused on monosubstituted coumarins.…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions

Lyapchev

Koleva

et al. 2022

Molecules

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Quantum-chemical calculations on the spectral properties of some aryl substituted 3-phosphonocoumarins were performed, and the effect of the substituents in the aryl moiety was evaluated. The structures possessing promising fluorescent properties were successfully synthesized via Suzuki and Sonogashira cross-coupling. The synthetic protocol was also applied for the phosphorous chemoisomer of 3-phosphonocoumarin, 1,2-benzoxaphosphorin, and their carboxylate analogues. The optical properties of the arylated and alkynylated products were experimentally determined. The obtained quantum-chemical and experimental results give the possibility for a fine tuning of the optical properties of phosphorous-containing coumarin systems by altering the substituent at its C-6 position.

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Synthesis of novel coumarin containing conjugated fluorescent polymers by Suzuki cross-coupling reactions and their chemosensing studies for iron and mercury ions

Cited by 14 publications

References 56 publications

Coumarin‐based Chemosensors for Metal Ions Detection

Coumarin‐based Chemosensors for Metal Ions Detection

Amino Acid Groups Enable Electrosynthesized Polyfluorenes to Specifically Recognize Cr₂O₇^2–

Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions

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Synthesis of novel coumarin containing conjugated fluorescent polymers by Suzuki cross-coupling reactions and their chemosensing studies for iron and mercury ions

Cited by 14 publications

References 56 publications

Coumarin‐based Chemosensors for Metal Ions Detection

Coumarin‐based Chemosensors for Metal Ions Detection

Amino Acid Groups Enable Electrosynthesized Polyfluorenes to Specifically Recognize Cr2O72–

Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions

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Amino Acid Groups Enable Electrosynthesized Polyfluorenes to Specifically Recognize Cr₂O₇^2–