Synthesis of Nanometer‐Sized, Rigid, and Hydrophobic Anions

Türp, David; Wagner, Manfred; Enkelmann, Volker; Müllen, Kläus

doi:10.1002/anie.201007070

Cited by 38 publications

(13 citation statements)

References 53 publications

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“…[48][49][50][51][52][53][54][55][56][57][58][59] Anionic PPDs have been synthesized up to the 3 rd generation from an ethynyl functionalized tetraphenylborate core, as seen in Figure 3, which lead to the formation of weakly coordinating anions (WCAs). 60 The boron core had to be stabilized by four electron withdrawing tetrafluorophenyl groups in order to enable the build-up for higher generations. The introduction of fluorine atoms to the inner phenylene rings caused the appearance of several conformational isomers (atropisomers), which hampered the crystallization of higher generation borate salts.…”

Section: Dendrimer Corementioning

confidence: 99%

“…Finally, a further enhancement of ion dissociation was observed when pentafluorophenyl-or 3,5-bis(trifluoromethyl)phenyl units were attached to the dendrimer surface (see Figure 4). 60 Thus, the powerful concept of dendronization is reflected by its versatile ability to tailor ion dissociation and solubility for both cationic and anionic species. The size of the PPD scaffold, the degree of branching (A 2 B or A 4 B growth step) as well as surface functionalization (fluorination, CF 3 decoration) can be specifically addressed in order to control electrolyte properties in organic solvents.…”

Section: Dendrimer Corementioning

confidence: 99%

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The polar side of polyphenylene dendrimers

et al. 2015

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Polyphenylene dendrimers (PPDs) represent a unique class of dendrimers based on their rigid, shape persistent chemical structure. These macromolecules are typically looked at as nonpolar precursors for conjugated systems. Yet over the years there have been synthetic achievements that have produced PPDs with a range of polarities that break the hydrophobic stereotype, and provide dendrimers that can be synthetically tuned to be used in applications such as stable transition metal catalysts, nanocarriers for biological drug delivery, and sensors for volatile organic compounds (VOCs), among many others. This is based on strategies that allow for the modification of PPDs at the core, scaffold, and surface to introduce numerous different groups, such as electrolytes, ions, or other polar species. This review is aimed to demonstrate the versatility of PPDs through their site-specific chemical functionalization to produce robust materials with various polarities.

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Section: Dendrimer Corementioning

confidence: 99%

Section: Dendrimer Corementioning

confidence: 99%

The polar side of polyphenylene dendrimers

et al. 2015

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“…The following compounds were synthesized by adaptation and modification of the literature procedures; Me-TEG-Mesyl [ 51 ], Me-TEG-N 3 [ 52 ], HO-TEG-mesyl [ 53 ], HO-TEG-N 3 [ 53 ], 1 [ 54 ], and 4 – 6 [ 55 , 56 , 57 ]. Details of the synthesis of compounds 7 – 14 , and SPIONs stabilized by oleic acid (OA) [ 30 ], are provided in the supplementary materials section .…”

Section: Methodsmentioning

confidence: 99%

Fabricating Water Dispersible Superparamagnetic Iron Oxide Nanoparticles for Biomedical Applications through Ligand Exchange and Direct Conjugation

et al. 2016

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Stable superparamagnetic iron oxide nanoparticles (SPIONs), which can be easily dispersed in an aqueous medium and exhibit high magnetic relaxivities, are ideal candidates for biomedical applications including contrast agents for magnetic resonance imaging. We describe a versatile methodology to render water dispersibility to SPIONs using tetraethylene glycol (TEG)-based phosphonate ligands, which are easily introduced onto SPIONs by either a ligand exchange process of surface-anchored oleic-acid (OA) molecules or via direct conjugation. Both protocols confer good colloidal stability to SPIONs at different NaCl concentrations. A detailed characterization of functionalized SPIONs suggests that the ligand exchange method leads to nanoparticles with better magnetic properties but higher toxicity and cell death, than the direct conjugation methodology.

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“…[43,44] Similar to many other tetraaryl-substituted cyclopentadienones, the torsion angle of the two phenyl rings bound to the C2 and C5 is smaller than for the two rings bound to C3 and C4. [15,[43][44][45][46][47][48] This can be explained by the fact, that the C2 and C5 substituents possess access to "open space" around the C=O group, whereas the C3 and C4 substituents experience steric pressure from two neighboring aryl rings.…”

Section: Crystal Structure Analysismentioning

confidence: 99%

Tetraaryl Cyclopentadienones: Experimental and Theoretical Insights into Negative Solvatochromism and Electrochemistry

Meitinger¹,

Mengele²,

Witas³

et al. 2020

Eur J Org Chem

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The synthesis of a series of tetraaryl cyclopentadienones comprising different substitution patterns is reported. Their photophysical and electrochemical properties are investigated by UV/Vis spectroscopy and cyclic voltammetry as well as by supporting quantum chemical simulations and reveal a distinct effect of substituents on the redox behavior of the molecules as well as the absorption properties of this class of compounds. While electrochemical data display a shift in reduction potential of up to 200 mV between the differently substituted cyclopentadienones, their photophysical investigations in differently polar solvents suggest a negative solvatochromic effect, although protic solvents induce a bathochromic shift. Crystal structure analyses of some derivatives confirm similarity with related cyclopentadienones while providing insight into intermolecular C–H···O and C–H···π interactions in the solid state.

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Synthesis of Nanometer‐Sized, Rigid, and Hydrophobic Anions

Cited by 38 publications

References 53 publications

The polar side of polyphenylene dendrimers

The polar side of polyphenylene dendrimers

Fabricating Water Dispersible Superparamagnetic Iron Oxide Nanoparticles for Biomedical Applications through Ligand Exchange and Direct Conjugation

Tetraaryl Cyclopentadienones: Experimental and Theoretical Insights into Negative Solvatochromism and Electrochemistry

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