Introduction of a (Ph<sub>3</sub>P)<sub>2</sub>Pt group into the rim of an open-cage fullerene by breaking a carbon–carbon bond

Gralinski, Steven; Roy, Mrittika; Baldauf, Lilia M.; Olmstead, Marilyn M.; Balch, Alan L.

doi:10.1039/d1cc04336f

Cited by 4 publications

(5 citation statements)

References 26 publications

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“…The surface contact angle of TpDMB-COPs-MMM was increased due to the hydrophobic nature of the carbon-carbon double bond skeleton of TpDMB-COPs. These results confirmed the successful synthesis of TpDMB-COPs-MMM [38].…”

Section: Characterization Of Tp-dmb-cops and Tp-dmb-cops-mmmsupporting

confidence: 81%

Preparation of COPs Mixed Matrix Membrane for Sensitive Determination of Six Sulfonamides in Human Urine

Liu,

Zhang,

Wang

et al. 2023

Molecules

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In this study, TpDMB-COPs, a specific class of covalent organic polymers (COPs), was synthesized using Schiff-base chemistry and incorporated into a polyvinylidene fluoride (PVDF) polymer for the first time to prepare COPs mixed matrix membranes (TpDMB-COPs-MMM). A membrane solid-phase extraction (ME) method based on the TpDMB-COPs-MMM was developed to extract trace levels of six sulfonamides from human urine identified by high-performance liquid chromatography (HPLC). The key factors affecting the extraction efficiency were investigated. Under the optimum conditions, the proposed method demonstrated an excellent linear relationship in the range of 3.5–25 ng/mL (r2 ≥ 0.9991), with the low limits of detection (LOD) between 1.25 ng/mL and 2.50 ng/mL and the limit of quantification (LOQ) between 3.50 ng/mL and 7.00 ng/mL. Intra-day and inter-day accuracies were below 5.0%. The method’s accuracy was assessed by recovery experiments using human urine spiked at three levels (7–14 ng/mL, 10–15 ng/mL, and 16–20 ng/mL). The recoveries ranged from 87.4 to 112.2% with relative standard deviations (RSD) ≤ 8.7%, confirming the applicability of the proposed method. The developed ME method based on TpDMB-COPs-MMM offered advantages, including simple operation, superior extraction affinity, excellent recycling performance, and easy removal and separation from the solution. The prepared TpDMB-COPs-MMM was demonstrated to be a promising adsorbent for ME in the pre-concentration of trace organic compounds from complex matrices, expanding the application of COPs and providing references for other porous materials in sample pre-treatment.

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Section: Characterization Of Tp-dmb-cops and Tp-dmb-cops-mmmsupporting

confidence: 81%

Preparation of COPs Mixed Matrix Membrane for Sensitive Determination of Six Sulfonamides in Human Urine

Liu,

Zhang,

Wang

et al. 2023

Molecules

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“…Cyclic voltammetry in o-dichlorobenzene reveals that (Ph 3 P) 2 Pt-MMK-9 undergoes a one-electron reduction at a potential considerably more negative than that of MMK-9 itself. 37 Two other related oxidative addition reactions involving C-C bond breaking and oxidative addition to Pt(0) are outlined in Scheme 2. Both require higher temperatures and longer reaction times than needed for the addition of (Ph 3 P) 4 Pt to MMK-9.…”

Section: Reaction With (Ph 3 P) 4 Ptmentioning

confidence: 99%

“…Addition of (Ph 3 P) 4 Pt to MMK-9 in dioxygen-free toluene produced the adduct (Ph 3 P) 2 Pt-MMK-9 in 46% yield after 90 minutes of stirring at room temperature. 37 The structure of the adduct is shown in Fig. 5.…”

Section: The Unexpected Reactivity Of the Open-cage Fullerene Mmk-9mentioning

confidence: 99%

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Open-cage fullerenes as ligands for metals

Balch

2024

Dalton Trans.

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“…Over the past few years, rhombicuboctahedron C 60 @Cu 24 and metal-chain-wired fullerene (Pd 4 ) 2 C 60 were prepared as a novel type of metal–carbon nanocomposite materials which exhibit strong absorption in the visible region or chiroptical properties. With these mature synthetic methodologies in hand, however, preparation of transition metal complexes based on open-[60]fullerenes still remains challenging, and only a few examples have been reported, with less attention paid to their electronic properties thus far. − Herein, we showcase the synthesis of near-infrared (NIR) absorbing cobalt-functionalized open-[60]fullerenes, i.e., mono- and dinuclear complexes, the former of which was suggested to lead to a characteristic redox behavior (Figure ).…”

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confidence: 99%

Cobalt-Functionalized Open-[60]Fullerenes

Hashikawa,

Murata

2024

Organometallics

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Redox noninnocent ligands have drawn considerable attention owing to effective interplay with metal(s) via π−d interactions, enabling magnetic on/off switching as well as redox-controlled catalytic reactions. Herein, we showcase the synthesis of [Co] 2 and [Co] 1 complexes bearing open-[60]fullerene ligands, whose absorption edges reached 1000 and 1500 nm, respectively. During the reaction, o-dichlorobenzene (solvent) was partly transformed to 2-chlorophenol, with which the Co complexes are most likely to participate in a reductive elimination step. While [Co] 2 contains a Co−Co bond identifiable by hybridized d z 2 orbitals, [Co] 1 possesses a fulveneconjugated open-[60]fullerene ligand which was generated by a ring-opening metathesis. Theoretical calculations suggested that [Co] 1 shows characteristic redox behavior where the ligand works as an electron reservoir.

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Introduction of a (Ph₃P)₂Pt group into the rim of an open-cage fullerene by breaking a carbon–carbon bond

Abstract: Treatment of an open-cage fullerene, designated as MMK-9, with (Ph3P)4Pt in toluene solution at room temperature allows a Pt(PPh3)2 unit to be incorporated into the rim of the cage so...

Cited by 4 publications

References 26 publications

Preparation of COPs Mixed Matrix Membrane for Sensitive Determination of Six Sulfonamides in Human Urine

Preparation of COPs Mixed Matrix Membrane for Sensitive Determination of Six Sulfonamides in Human Urine

Open-cage fullerenes as ligands for metals

Cobalt-Functionalized Open-[60]Fullerenes

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Introduction of a (Ph3P)2Pt group into the rim of an open-cage fullerene by breaking a carbon–carbon bond

Abstract: Treatment of an open-cage fullerene, designated as MMK-9, with (Ph3P)4Pt in toluene solution at room temperature allows a Pt(PPh3)2 unit to be incorporated into the rim of the cage so...

Cited by 4 publications

References 26 publications

Preparation of COPs Mixed Matrix Membrane for Sensitive Determination of Six Sulfonamides in Human Urine

Preparation of COPs Mixed Matrix Membrane for Sensitive Determination of Six Sulfonamides in Human Urine

Open-cage fullerenes as ligands for metals

Cobalt-Functionalized Open-[60]Fullerenes

Contact Info

Product

Resources

About

Introduction of a (Ph₃P)₂Pt group into the rim of an open-cage fullerene by breaking a carbon–carbon bond