Addition of azomethine ylides to carbon-encapsulated iron nanoparticles

Kasprzak, Artur; Nowicka, Anna M.; Sęk, Jakub P.; Fronczak, Maciej; Bystrzejewski, M.; Koszytkowska‐Stawińska, Mariola; Popławska, Magdalena

doi:10.1039/c7dt03689b

Cited by 9 publications

(7 citation statements)

References 37 publications

(33 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The first weight loss up to 110 °C is related to the presence of moisture in the studied sample. The next weight loss, which starts at 120 °C and is completed at 500 °C, is associated with the presence of the organic moieties attached to CEINs ,,,. Please note that the latter weight loss is not observed for the pristine CEINs.…”

Section: Resultsmentioning

confidence: 96%

“…On a contrary, a dark‐green supernatant was observed for material 10 (Figure , c). This shows that Fc + was formed, and Fc was released from its inclusion complex with βCD . 5‐Fluorouracil (5‐FU) was then complexed inside the as‐formed “free” βCD's inner cavity.…”

Section: Resultsmentioning

confidence: 99%

“…Carbon‐encapsulated iron nanoparticles (CEINs) have the core‐shell structure. The metallic iron core is encapsulated in the tight carbon coating which is made of few‐layer graphene . The carbon coating in CEINs is to protect the metallic core against oxidation and agglomeration or aggregation.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Folic Acid‐Navigated and β‐Cyclodextrin‐Decorated Carbon‐Encapsulated Iron Nanoparticles as the Nanotheranostic Platform for Controlled Release of 5‐Fluorouracil

et al. 2018

Self Cite

View full text Add to dashboard Cite

The theranostic probe based on carbon‐encapsulated iron nanoparticles (CEINs) is presented. First, the conjugates of CEINs and polyethylenimine (PEI) were obtained to modify the surface of CEINs with amino groups. It was archived either by means of direct radical addition of PEI to CEINs (CEINs‐NH‐PEI material) or the amidation‐type reaction between CEINs∼COOH and the polymer (CEINs∼CONH‐PEI material obtained). β‐Cyclodextrin (βCD) was selected as the drug delivery vector. βCD was covalently anchored to the PEI‐functionalized CEINs via the 1,1’‐carbonyldiimidazole‐mediated reaction. The synthesis included the conjugation of folic acid (FA; targeting ligand) to CEINs via the carbodiimide‐mediated amidation‐type process. The innovative method for excluding a side process of the FA@βCD complex formation during the FA conjugation to PEI, was developed. 5‐Fluorouracil (5‐FU) was chosen as the representative drug molecule. 5‐FU was anchored to the CEINs∼PEI∼βCD∼FA nanoplatforms employing the host‐guest chemistry of βCD. The success of the reactions was confirmed by infrared spectroscopy and thermogravimetry. The content of anchored organic compounds depends on the type of linkage between PEI and CEINs. Additionally, 5‐FU release profile was examined at various pH. The highest release of 5‐FU was observed at pH 9.0, whilst the lowest at pH 4.7. This work sheds a new light on application of carbon‐encapsulated iron nanoparticles in nanomedicine as the novel drug delivery theranostic systems.

show abstract

Section: Resultsmentioning

confidence: 96%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Folic Acid‐Navigated and β‐Cyclodextrin‐Decorated Carbon‐Encapsulated Iron Nanoparticles as the Nanotheranostic Platform for Controlled Release of 5‐Fluorouracil

et al. 2018

Self Cite

View full text Add to dashboard Cite

show abstract

“…It should be noted that the materials differ in the type of linker between the CEINs and Fc as well as in content of the Fc moiety (21.2, 16.3, and 6.3 wt % for CEINs-Fc-1 , CEINs-Fc-2 , and CEINs-Fc-3 , respectively). Importantly, cyclic voltammetry studies revealed the electrochemical activity of the nanoconjugates, as the fully reversible redox processes of the Fc ligand attached to CEINs were observed. − It should be noted that transmission electron microscopy studies of various functionalized CEINs (including CEINs-Fc-2 ) revealed that the core–shell morphology of the obtained materials is retained after their surface modification, and no surface degradation after the functionalization is observed. ,,, …”

Section: Resultsmentioning

confidence: 96%

“…The structures of the materials (CEINs-Fc-1−CEINs-Fc-3) are presented in Figure 1. The materials were obtained via the one-step cycloaddition reaction (CEINs-Fc-1 47 and CEINs-Fc-2 48 ) or the three-step protocol (CEINs-Fc-3). 49 It should be noted that the materials differ in the type of linker between the CEINs and Fc as well as in content of the Fc moiety (21.2, 16.3, and 6.3 wt % for CEINs-Fc-1, CEINs-Fc-2, and CEINs-Fc-3, respectively).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Ferrocene-Labeled Carbon-Encapsulated Iron Nanoparticles: The First Magnetic Nanocatalysts for C–H Arylation toward 1,1′-Biphenyl Formation

Kasprzak

Bystrzejewski

Popławska

2019

Org. Process Res. Dev.

Self Cite

View full text Add to dashboard Cite

The first magnetic nanocatalysts for C–H arylation toward 1,1′-biphenyl formation are described. The nanocatalysts are based on conjugates of ferrocene and carbon-encapsulated iron nanoparticles. The highest catalytic activity was found for ferrocene conjugated to carbon-encapsulated iron nanoparticles via the N-methylpyrrolidine moiety. In the presence of the nanocatalyst, various 1,1′-biphenyls can be obtained in high yields (84–90%). The effect of substitution of the aniline’s phenyl ring on the reaction yield is also included in this work. The nanocatalyst can be easily separated from the reaction mixture and can be reused in up to four reaction cycles without any loss of its high catalytic activity. Our work sheds light on a potential application of functionalized carbon-encapsulated iron nanoparticles in modern industrial organic processes toward more economical manufacturing of organic compounds.

show abstract