Self-Assembled Fluorinated Organogelators for Surface Modification

Raghavanpillai, Anilkumar; Franco, Vincent A.

doi:10.3390/app2010175

Cited by 10 publications

(4 citation statements)

References 40 publications

(45 reference statements)

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“…Slight variations on the polarity of the gelator may either improve or reduce its gelling ability depending on the solvent used for the process [ 14 , 19 , 20 ]. Several works reported the influence of fluorine on the physical properties and self-assembly ability of different types of compounds [ 21 , 22 , 23 , 24 ]. Nilsson reported the efficient hydrogelation of Fmoc-protected pentafluorophenylalanine (Fmoc-F 5 -Phe) [ 25 ].…”

Section: Introductionmentioning

confidence: 99%

Fluorine Effect in the Gelation Ability of Low Molecular Weight Gelators

Ravarino

Domenico

Barbalinardo

et al. 2022

Gels

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The three gelators presented in this work (Boc-D-Phe-L-Oxd-OH F0, Boc-D-F1Phe-L-Oxd-OH F1 and Boc-D-F2Phe-L-Oxd-OH F2) share the same scaffold and differ in the number of fluorine atoms linked to the aromatic ring of phenylalanine. They have been applied to the preparation of gels in 0.5% or 1.0% w/v concentration, using three methodologies: solvent switch, pH change and calcium ions addition. The general trend is an increased tendency to form structured materials from F0 to F1 and F2. This property ends up in the formation of stronger materials when fluorine atoms are present. Some samples, generally formed by F1 or F2 in 0.5% w/v concentration, show high transparency but low mechanical properties. Two gels, both containing fluorine atoms, show increased stiffness coupled with high transparency. The biocompatibility of the gelators was assessed exposing them to fibroblast cells and demonstrated that F1 and F2 are not toxic to cells even in high concentration, while F0 is not toxic to cells only in a low concentration. In conclusion, the presence of even only one fluorine atom improves all the gelators properties: the gelation ability of the compound, the rheological properties and the transparency of the final materials and the gelator biocompatibility.

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Section: Introductionmentioning

confidence: 99%

Fluorine Effect in the Gelation Ability of Low Molecular Weight Gelators

Ravarino

Domenico

Barbalinardo

et al. 2022

Gels

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“…[ 26,46 ] The fl uorinated isocyanates were synthesized in two steps using a procedure described in the literature. [ 47 ] The synthesis involves the reaction of the fl uorinated acids in the presence of PCl 5 to lead to acyl chlorides, following by a reaction with trimethylsilyl chloride to produce after heating the fl uorinated isocyanates.…”

Section: Methodsmentioning

confidence: 99%

Highly Polar Linkers (Urea, Carbamate, Thiocarbamate) for Superoleophobic/Superhydrophobic or Oleophobic/Hydrophilic Properties

Darmanin

Guittard

2015

Adv Materials Inter

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Due to the much lower surface tension of oils in comparison to water, it is extremely difficult to obtain superoleophobic properties and also both oleophobic and hydrophilic properties. While the obtaining of superoleophobic properties needs extremely complex surface structures such as reentrant structures to impede the oil wetting, the obtaining of both oleophobic and hydrophilic properties needs the use of both oleophobic materials (fluorinated materials) and hydrophilic materials (charged or polar species). Here, by electropolymerization of original 3,4‐ethylenedioxythiophene derivatives containing both fluorinated chains (C8F17, C6F13, or C4F9) and highly polar linkers (thiocarbamate SCONH, carbamate OCONH, and urea NHCONH), the possibility to obtain superoleophobic properties and also both oleophobic and hydrophilic properties is reported for the first time. More precisely superoleophobic properties are obtained with different fluorinated chain lengths and linkers while the obtaining of both oleophobic and hydrophilic properties is possible only with the most polar urea NHCONH linkers.

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“…The fluorinated isocyanate was synthesized from a fluorinated acid chloride in the presence of trimethylsilyl azide . 2‐(2,3‐Dihydro‐[1,4]dioxino[2,3‐ c ]pyrrol‐6‐yl)ethanol (EDOP‐OH) was synthesized in ten steps from iminodiacetic acid using a procedure reported in the literature (Scheme ) …”

Section: Methodsmentioning

confidence: 99%

Bioinspired Rose‐Petal‐Like Substrates Generated by Electropolymerization on Micropatterned Gold Substrates

et al. 2016

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optimization of physical chemical methods to characterize nano-materials and nanostructures in order to study their interactions with cells and biomolecules and thereby assess their safety/bio-compatibility.S ubsequently,D r. Darmanin was made associate professor in the group of Prof. FrØdØric Guittard (NICE Lab, UniversitØ Côte d'Azur (UCA)). The focus of the group is to design novel su-perhydrophobic/superoleophobic surfaces by controlling the surface nanostructures (nanofibers, nanotubes, nanosheets) through electropolymerization. Moreover,t he adhesion of various liquids on these structured surfaces is studies. For such investigations, it is often necessary to combine two techniques to create micro-and nanoscale structures, in order to enhance the surface properties. Hence, collaboration was necessary to develop micro-patterned gold substrates by soft lithography (carried out at JRC) and to elec-tropolymerization on these substrates (carried out at NICE Lab). What are the main challengesi nthe broad area of your research? The main challenge in our field is the control of surface structures at both am icro-and nanoscale. Control of the surface is crucial to better understand the surface wetting properties from atheoretical point of view.V arious methods can be used to create micro-and nanostructures, lithographic techniques are probably the most flexible and can be applied to the design of well-defined, micropat-terned substrates. Electropolymerization is also au nique technique which induces the growth surface structures of various shapes (nanofibers, nanotubes, nanosheets, nanoparticles). What was the biggest surprise (on the way to the results presentedi nthis paper)? The biggest surprise was the huge influence of the micropattern-ing specifications (pillar diameter and pitch) and the electrochemi-cal parameters on the surface hydrophobicity and water adhesion. Moreover,i sw as possible to obtain the characteristics of extremely high apparent contact angles (up to 1608)a nd extremely high water adhesion, as observed in nature on rose petals. Such materials are extremely interesting for applications such as water harvesting and oil/water separation membranes. Invited for this month'sc over are the collaborating groups of Dr.T hierry Darmanin at UniversitØ Côte d'Azur,F rance and Dr.F ranÅois Rossi at JRC European Commission, Italy.T he cover picture shows an ovel strategy for preparing substrates having ar ose-petal effect (high water adhesion). The micropatterning specifications (pillar diameter and pitch) and the elec-tropolymerization parameters are key to obtaining both high water apparent contacta ngles and ah igh hysteresis. Read the full text of the article at

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Self-Assembled Fluorinated Organogelators for Surface Modification

Cited by 10 publications

References 40 publications

Fluorine Effect in the Gelation Ability of Low Molecular Weight Gelators

Fluorine Effect in the Gelation Ability of Low Molecular Weight Gelators

Highly Polar Linkers (Urea, Carbamate, Thiocarbamate) for Superoleophobic/Superhydrophobic or Oleophobic/Hydrophilic Properties

Bioinspired Rose‐Petal‐Like Substrates Generated by Electropolymerization on Micropatterned Gold Substrates

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