Synthesis and Linker‐Controlled Self‐Assembly of Dendritic Amphiphiles with Branched Fluorinated Tails

Singh, Abhishek Kumar; Schade, Boris; Rosati, Marta; Rashmi, Rashmi; Dichiarante, Valentina; Cavallo, Gabriella; Metrangolo, Pierangelo; Haag, Rainer

doi:10.1002/mabi.202200108

Cited by 6 publications

(19 citation statements)

References 47 publications

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“…[27] As a consequence of its electroneutrality, its removal efficiency of cationic, neutral, and zwitterionic PFAs was comparable to the removal efficiency of the most commonly addressed negatively charged PFOS. Broadening and a slight shift of the 19 F NMR signal from the CF 3 group of the studied PFAs was only observed in the presence of fluorous poly(methacrylamide) particles. No changes in the 19 F NMR spectra of the PFAs were observed when the PFAs were mixed with the corresponding non-fluorous poly(methacrylamide) particles, a result that instead indicates there is a fluorous interaction in the adsorption process of PFAs onto the fluorous particles of the hydrogel.…”

Section: Fluorous Adsorption Of Fluorinated Amphiphiles At Surfacesmentioning

confidence: 85%

Interfaces with Fluorinated Amphiphiles: Superstructures and Microfluidics

et al. 2023

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This Minireview discusses recent developments in research on the interfacial phenomena of fluorinated amphiphiles, with a focus on applications that exploit the unique and manifold interfacial properties associated with these amphiphiles. Most notably, fluorinated amphiphiles form stable aggregates with often distinctly different morphologies compared to their nonfluorinated counterparts. Consequently, fluorinated surfactants have found wide use in high-performance applications such as microfluidic-assisted screening. Additionally, their fluorine-specific behaviour at solid/liquid interfaces, such as the formation of superhydrophobic coatings after deposition on surfaces, will be discussed. As fluorinated surfactants and perfluorinated materials in general pose potential environmental threats, recent developments in their remediation based on their adsorption onto fluorinated surfaces will be evaluated.

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Section: Fluorous Adsorption Of Fluorinated Amphiphiles At Surfacesmentioning

confidence: 85%

Interfaces with Fluorinated Amphiphiles: Superstructures and Microfluidics

et al. 2023

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“…Singh et al [19] . berichteten von zwei nichtionischen verzweigten Amphiphilen mit zwei unterschiedlichen chemischen Ansätzen (Amid‐ und Triazol‐Kupplung), um das gleiche fluorierte Dendron mit einem G2‐Oligoglycerin‐Dendron zu verbinden.…”

Section: Flüssig/flüssig‐grenzflächenunclassified

“…Von Berlepsch et al [17] Ein ähnlicher Übergang von Überstrukturen von fluorierten dendritischen Amphiphilen vom Janus-Typ wurde in einer aktuellen Arbeit von Rosati und Mitarbeitern beobachtet. [18] Singh et al [19] berichteten von zwei nichtionischen verzweigten Amphiphilen mit zwei unterschiedlichen chemischen Ansätzen (Amid-und Triazol-Kupplung), um das gleiche fluorierte Dendron mit einem G2-Oligoglycerin-Dendron zu verbinden. Beide Verbindungen zeigten die Bildung gut definierter Vesikel, aber bedingt durch die verschiedenen Linker ein leicht unterschiedliches Aggregationsverhalten.…”

Section: Flüssig/flüssig-grenzflächen 21 Supramolekulare Architekture...unclassified

Grenzflächen mit fluorierten Amphiphilen: Überstrukturen und Mikrofluidik

et al. 2023

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Abbildung 4. a) Allgemeine chemische Struktur der Gelatoren auf der Grundlage des Cyclohexyl-Diamid-Kerns. b) Vorgeschlagener Aufbaumechanismus für den C 7 F 15 -substituierten Gelator. [31] c)-e) Zweistufige hierarchische Struktur der selbstorganisierten Strukturen von Gelatoren mit verschiedenen Seitenketten. [31,32] f)-h) Selbstreinigung gegenüber Blut auf geschmierter gleitfähiger Oberfläche. [31] i) und j) Lichtmikroskopische Aufnahmen, die das unterschiedliche Ausmaß der Beeinträchtigung während der Wasserflussstabilitätstests der hergestellten Beschichtungen zeigen. [32] k) und l) Veränderung des makroskopischen Aussehens der Beschichtungen in (i) bzw. (j), analysiert anhand der Pixelhelligkeit. [32] Abbildung adaptiert mit Genehmigung von Wei et al. [31] und Lee et al. [32]

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“…When the linker between the fluorinated and hydrophilic sides was changed, self-assembly in water of these nonionic branched amphiphiles gave either multivesicular and multilamellar vesicles, or smaller unilamellar vesicles. In all cases, the resulting supramolecular architectures showed negligible cytotoxicity and good potential for drug delivery applications …”

Section: Multibranched Partially Fluorinated Perfecta Derivativesmentioning

confidence: 99%

“…In all cases, the resulting supramolecular architectures showed negligible cytotoxicity and good potential for drug delivery applications. 50…”

Section: F27 Functionalized Molecules and Macromoleculesmentioning

confidence: 99%

Multibranched-Based Fluorinated Materials: Tailor-Made Design of ¹⁹F-MRI Probes

et al. 2022

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Conspectus Future medicine is primarily aiming at the development of novel approaches for an early diagnosis of diseases and a personalized therapy for patients. For achieving these objectives, a key role is played by medical imaging. Among available noninvasive imaging techniques, Fluorine-19 (19F) Magnetic Resonance Imaging (MRI) is emerging as a powerful quantitative detection modality for clinical use both for molecular imaging and for cell tracking. The strength of using 19F-MRI is mainly related to the lack of endogenous organic fluorine in tissues, with no background, enabling the visualization of fluorinated tracers as hot-spot images, adding secondary independent information to the anatomical features provided by the grayscale 1H-MRI. The main challenge for 19F-MRI clinical application is the intrinsic reduced sensitivity of MRI. To improve sensitivity, undoubtedly the use of a high field MRI scanner and cryogenic radiofrequency probes is advantageous, but there is a clear need of developing increasingly effective fluorinated tracers. The ideal tracer should bear as many as possible magnetically equivalent fluorine atoms and show optimal magnetic resonance relaxivity properties (i.e., T 1 and T 2), which enable reduced acquisition time with the possibility to apply fast imaging methods. Moreover, it should be biocompatible with reduced tendency to bioaccumulate in tissues, which is one of the main drawbacks in using perfluorocarbons (PFCs), together with their difficulty to be chemically modified with functional groups. In fact, PFCs such as perfluorooctyl bromide (PFOB), perfluoro-15-crown-5-ether (PFCE), and linear perfluoropolyethers (PFPE) are currently the most used tracers in 19F-MRI preclinical and clinical studies, with the above-mentioned limitations. In this regard, molecules bearing short branched fluorinated chains gained a lot of attention for their high number of equivalent fluorines and expected capability of reducing bioaccumulation concerns. A valuable building block for branched fluorinated tracers is perfluoro-tert-butanol (PFTB), with nine magnetically equivalent fluorines and easy availability and modification. In this Account we will discuss the main challenges that 19F-MRI has to overcome for increasing its clinical use, highlighting on one hand the need of developing customized fluorinated materials for increasing sensitivity and enabling multimodal properties, and on the other hand, the importance of the ultrastructure of the final formulation for the final biological response (i.e., clearance). In this context, our group has been focusing on the synthesis and development of branched fluorinated tracers, for which the originator is a molecule called PERFECTA (from suPERFluorinatEdContrasT Agent), bearing 36 equiv 19F atoms, which showed not only optimal relaxometry properties but also a very specific and intense Raman signal. Thus, PERFECTA and its derivatives represent a new family of multimodal tracers enabling multiscale analysis, from whole body imaging (19F-MRI) to microsco...

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Synthesis and Linker‐Controlled Self‐Assembly of Dendritic Amphiphiles with Branched Fluorinated Tails

Cited by 6 publications

References 47 publications

Interfaces with Fluorinated Amphiphiles: Superstructures and Microfluidics

Interfaces with Fluorinated Amphiphiles: Superstructures and Microfluidics

Grenzflächen mit fluorierten Amphiphilen: Überstrukturen und Mikrofluidik

Multibranched-Based Fluorinated Materials: Tailor-Made Design of ¹⁹F-MRI Probes

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Synthesis and Linker‐Controlled Self‐Assembly of Dendritic Amphiphiles with Branched Fluorinated Tails

Cited by 6 publications

References 47 publications

Interfaces with Fluorinated Amphiphiles: Superstructures and Microfluidics

Interfaces with Fluorinated Amphiphiles: Superstructures and Microfluidics

Grenzflächen mit fluorierten Amphiphilen: Überstrukturen und Mikrofluidik

Multibranched-Based Fluorinated Materials: Tailor-Made Design of 19F-MRI Probes

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Multibranched-Based Fluorinated Materials: Tailor-Made Design of ¹⁹F-MRI Probes