Organogel formation rationalized by Hansen solubility parameters: dos and don'ts

Bonnet, Julien; Suissa, Gad; Raynal, Matthieu; Bouteiller, Laurent

doi:10.1039/c4sm00244j

Cited by 70 publications

(68 citation statements)

References 70 publications

(131 reference statements)

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“…Over the seventeen tested solvents, nine proved to be gelled by compound 1 (Figure 1 and Table S1), with moderate critical gelation concentrations comprised between 10 and 50 mg.mL -1 (2.10 -2 -10 -1 mol.L -1 ). Though no obvious correlation between the physicochemical properties of the solvents and the obtaining of a gel phase could be highlighted (See Table S1 and Figure S1), 24 these results confirm the relevance of our strategy to design gelator 1. The corresponding solid materials obtained after evaporation of the solvent, i.e.…”

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confidence: 66%

Promoting Spontaneous Second Harmonic Generation through Organogelation

et al. 2016

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-An organogelator based on the Disperse Red NLO-phore was synthesized according to a simple and efficient three-step procedure. The supramolecular gel organization leads to xerogels which display a spontaneous second harmonic generation (SHG) response without any need for pre-processing and this SHG activity appears stable over several months. These findings, based on an intrinsic structural approach are supported by favorable intermolecular supramolecular interactions, which promote a locally noncentrosymmetric NLO-active organization. This is in sharp contrast with most materials designed for SHG purposes, which generally require the use of expensive or heavy-tohandle external techniques for managing the dipoles alignment.Tremendous efforts are continuously dedicated to the development of better organic and SHG active materials for various applications in the fields of photonics, 1 optoelectronics, 2,3 or anti-counterfeiting. 4 Two major requirements have to be fulfilled in order to prepare these materials. Firstly, the corresponding molecules have to display strong hyperpolarizabilities. In this direction, hundreds of publications report the synthesis and characterizations of organic push-pull conjugated NLO-phores. 5,6 Secondly, the latter have to be organized in a non-centrosymmetric fashion in order to prevent destructive interferences between second harmonicgenerated photons. As a consequence, various approaches have been successfully considered in order to prepare SHGactive materials. These include the utilization of chiral compounds, 7,8 Langmuir-Blodgett films, 9 self-assembled layers, 10,11 elaborated matrices, 12 or corona poling. 13 Though efficient, these strategies require expensive conditions (i.e. chiral NLO-phores) or heavy-to-handle pre-treatments (e.g. corona poling) that impede their transfer at larger scales. Therefore, it appears of utmost interest to develop new methodologies to process SHG-active materials, by designing derivatives with specific functions able to promote the required organization for instance. The present work falls within this approach with the utilization of an organogelator. Gel-based materials have already shown their strong potential in the context of optoelectronics and photonics, 14-17 notably thanks to their high degree of organization at the supramolecular scale and their user-friendly processing. Various external methodologies have been developed in the past to promote the alignment of the micro-and nanofibers responsible for the gel state, be that through application of electric or magnetic fields along their formation or for instance shear stress.18-21 Conversely, our approach consisted in constraining SHG-active units in the desired non-centrosymmetric headto-head arrangement without any additional external mediation. This could be accomplished thanks to the use of urea moieties, well-known for both their narcissistic character in supramolecular chemistry and their ability to promote gelation.22 This proof-of-concept study was led on the Disperse Re...

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confidence: 66%

Promoting Spontaneous Second Harmonic Generation through Organogelation

et al. 2016

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“…In this case, the concentric sphere approach provides neither a good representation of the range of liquids that the gelator is (and is not) able to gelate nor the locations of the sphere centers. Also, there are only 3 and 4 solution data points for trans ‐9,10‐diol and trans ‐13,14‐diol, respectively; therefore, it is not possible to build creditable solution spheres for them either,4a and it is not known whether their centers match those of the gel spheres 3a. 46…”

Section: Resultsmentioning

confidence: 99%

Salicylato Titanocene Complexes as Cooperative Organometallic Lewis Acid and Brønsted Acid Catalysts for Three‐Component Mannich Reactions

Chen

Jia

et al. 2014

Chemistry A European J

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A binary acid system has been developed that features an air-stable organometallic precursor, titanocene dichloride, and simple organic cooperative Brønsted acids, which allowed for mild and highly efficient Mannich reactions of both aryl and alkyl ketones with excellent yields and satisfactory diastereoselectivity. Mechanistic studies, including (1) H NMR titration, X-ray structure analyses as well as isolation of catalytically active species, elucidated the dramatic synergistic effects of this new binary acid system.

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“…Among the different solubility models 33 , Hansen Solubility Parameters are widely used to predict material properties such as the affinity of substances to each other, gelation behavior of organogels 34 , encapsulation efficiency of drugs 35 , barrier function of release systems 36 as well as good and poor solvents for polymers 30, 37 .…”

Section: Introductionmentioning

confidence: 99%

Steering surface topographies of electrospun fibers: understanding the mechanisms

Yazgan

Dmitriev

Tyagi

et al. 2017

Sci Rep

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A profound understanding of how to tailor surface topographies of electrospun fibers is of great importance for surface sensitive applications including optical sensing, catalysis, drug delivery and tissue engineering. Hereby, a novel approach to comprehend the driving forces for fiber surface topography formation is introduced through inclusion of the dynamic solvent-polymer interaction during fiber formation. Thus, the interplay between polymer solubility as well as computed fiber jet surface temperature changes in function of time during solvent evaporation and the resultant phase separation behavior are studied. The correlation of experimental and theoretical results shows that the temperature difference between the polymer solution jet surface temperature and the dew point of the controlled electrospinning environment are the main influencing factors with respect to water condensation and thus phase separation leading to the final fiber surface topography. As polymer matrices with enhanced surface area are particularly appealing for sensing applications, we further functionalized our nanoporous fibrous membranes with a phosphorescent oxygen-sensitive dye. The hybrid membranes possess high brightness, stability in aqueous medium, linear response to oxygen and hence represent a promising scaffold for cell growth, contactless monitoring of oxygen and live fluorescence imaging in 3-D cell models.

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Organogel formation rationalized by Hansen solubility parameters: dos and don'ts

Cited by 70 publications

References 70 publications

Promoting Spontaneous Second Harmonic Generation through Organogelation

Promoting Spontaneous Second Harmonic Generation through Organogelation

Salicylato Titanocene Complexes as Cooperative Organometallic Lewis Acid and Brønsted Acid Catalysts for Three‐Component Mannich Reactions

Steering surface topographies of electrospun fibers: understanding the mechanisms

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