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UV initiated thiol-ene chemistry: a facile and modular synthetic methodology for the construction of functional 3D networks with tunable properties
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
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2013 (English)In: Journal of Materials Chemistry A, ISSN 2050-7488, Vol. 1, no 44, 13732-13737 p.Article in journal (Refereed) Published
Abstract [en]

A facile methodology for the fabrication of functional crosslinked three dimensional (3D) networks has herein been explored via the benign and UV initiated thiol-ene coupling (TEC) chemistry. The careful selection of monomers or polymers and their feed ratio resulted in straightforward design of organic, inorganic and hydrogel networks with readily available alkenes or thiol functional groups. All crosslinked networks were fabricated within 1 second of UV exposure at wavelengths of 320-390 nm and generally exhibited excellent gel fractions around 90%. By introducing off-stoichiometric thiol and ene (OSTE) monomer feed ratios the window of mechanical properties could be manipulated. For the organic triazine system, the Young's modulus was altered from 780 MPa at an equimolar monomer ratio to soft 106 kPa for 2.5 equiv. with excess of thiol compared to enes. Postfunctionalizations with hydrophilic polyethylene glycols or acrylic acid and hydrophobic heneicosa-fluorododecyl acrylate were explored for the manipulation of functional networks. In this case, the rigid networks with excess of thiols were used as model substrates of which the initial contact angle (CA) of 60 degrees was decreased to 43 degrees by the introduction of acrylic acid and increased to 140 degrees by successful attachment of fluorinated molecules. Finally, amalgamating micropatterning strategy with simple postfunctionalizations of hydrophobic groups resulted in superhydrophobic rigid surfaces with a CA of 173 degrees.

Place, publisher, year, edition, pages
2013. Vol. 1, no 44, 13732-13737 p.
Keyword [en]
Microfluidic Devices, Poly(Dimethylsiloxane), Strategies
National Category
Materials Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-136533DOI: 10.1039/c3ta12963bISI: 000326463400005Scopus ID: 2-s2.0-84886447725OAI: oai:DiVA.org:kth-136533DiVA: diva2:677061
Funder
Swedish Research Council, 2010-453
Note

QC 20131209

Available from: 2013-12-09 Created: 2013-12-05 Last updated: 2017-05-30Bibliographically approved
In thesis
1. Advanced polymeric scaffolds for functional materials in biomedical applications
Open this publication in new window or tab >>Advanced polymeric scaffolds for functional materials in biomedical applications
2014 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Advancements in the biomedical field are driven by the design of novel materials with controlled physical and bio-interactive properties. To develop such materials, researchers rely on the use of highly efficient reactions for the assembly of advanced polymeric scaffolds that meet the demands of a functional biomaterial. In this thesis two main strategies for such materials have been explored; these include the use of off-stoichiometric thiol-ene networks and dendritic polymer scaffolds. In the first case, the highly efficient UV-induced thiol-ene coupling (TEC) reaction was used to create crosslinked polymeric networks with a predetermined and tunable excess of thiol or ene functionality. These materials rely on the use of readily available commercial monomers. By adopting standard molding techniques and simple TEC surface modifications, patterned surfaces with tunable hydrophobicity could be obtained. Moreover, these materials are shown to have great potential for rapid prototyping of microfluidic devices. In the second case, dendritic polymer scaffolds were evaluated for their ability to increase surface interactions and produce functional 3D networks. More specifically, a self-assembled dendritic monolayer approach was explored for producing highly functional dendronized surfaces with specific interactions towards pathogenic E. coli bacteria. Furthermore, a library of heterofunctional dendritic scaffolds, with a controllable and exact number of dual-purpose azide and ene functional groups, has been synthesized. These scaffolds were explored for the production of cell interactive hydrogels and primers for bone adhesive implants. Dendritic hydrogels decorated with a selection of bio-relevant moieties and with Young’s moduli in the same range as several body tissues could be produced by facile UV-induced TEC crosslinking. These gels showed low cytotoxic response and relatively rapid rates of degradation when cultured with normal human dermal fibroblast cells. When used as primers for bone adhesive patches, heterofunctional dendrimers with high azide-group content led to a significant increase in the adhesion between a UV-cured hydrophobic matrix and the wet bone surface (compared to patches without primers).

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2014. 72 p.
Series
TRITA-CHE-Report, ISSN 1654-1081 ; 2014:1
Keyword
Dendrimer, hydrogel, PEG, dendritic monolayers, thiol-ene networks, off-stochiometric
National Category
Polymer Technologies Medical Materials Materials Chemistry Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-139944 (URN)978-91-7501-978-9 (ISBN)
Public defence
2014-01-31, F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (English)
Opponent
Supervisors
Note

QC 20140116

Available from: 2014-01-16 Created: 2014-01-15 Last updated: 2014-01-16Bibliographically approved
2. Advanced Functional Thin Films and Networks towards Biological Applications
Open this publication in new window or tab >>Advanced Functional Thin Films and Networks towards Biological Applications
2015 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Functional polymeric scaffolds have been employed in biological applications as several utilities, from nano-sized drug delivery systems to concrete implants. The progression in biological fields essentially relies on finding an appropriate material to fulfil the critical requirements for various types of applications with great potential for tuning functionality and mechanical properties. Therefore, the generation of new materials in extensive libraries is desirable for researchers. In this thesis, two main varieties of functional scaffolds have been constructed; these include i) periodic structure isoporous membranes and ii) three dimension (3D) crosslinked networks with programmable functionalities and mechanical properties. In the first case, a library of linear dendritic (LD) block copolymers was synthesised from biocompatible 2,2-bis(methylol)propionic acid (bis-MPA) dendrons and 2- hydroxyethyl methacrylate (HEMA) derivatives. These materials were successfully employed for the fabrication of isoporous membranes via the facile Breath Figure (BF) method. The dendritic periphery end groups control the manipulation of film morphology, as well as introduction of desired functionalities, either pre- or post- film formation. The introduction of azide functional group along the polymer backbone allows crosslinking reaction, which enhances the stability of the isoporous films. The stability towards temperature was improved from around its glass transition temperature (Tg) to 400 °C after crosslinking; simultaneously the porosity is maintained after immersion in the whole range of pH (1-14). These materials show great potential use as high performance isoporous membranes in futuristic applications such as micro-reactors, sensors and cell patterning platforms. In the second case, the facile fabrication of functional networks employs off-stoichiometric crosslinking, which resulted in residual reactive functional groups after film formation and networks with different crosslinking density. This straightforward off-stoichiometric concept is applied with commercially available materials and well-controlled dendritic-linear-dendritic (DLD) hybrid polymers, generating functional networks with different properties from high stiffness film to soft hydrogels. The network post-modification can be performed topologically and throughout the scaffold. Several crosslinking chemistries were employed for construction of hydrogels from DLD hybrid polymers. The Copper(I) Catalysed Azide-Alkyne Cycloaddition (CuAAC) click reaction results in hydrogels with higher compressive modulus compared to other hydrogels constructed from thiol-ene, thiol-yne and amine-N-hydroxysuccinimide (NHS) esters coupling methods with similar building blocks. These functional crosslinked networks are suitable for numerous applications including fabrication of microfluidic devices, cell culture platforms and bone adhesives.

 

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2015. 72 p.
Series
TRITA-CHE-Report, ISSN 1654-1081 ; 2015:23
National Category
Polymer Chemistry
Research subject
Chemistry
Identifiers
urn:nbn:se:kth:diva-166600 (URN)978-91-7595-552-0 (ISBN)
Public defence
2015-06-05, F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (English)
Opponent
Supervisors
Funder
VINNOVA
Note

QC 20150520

Available from: 2015-05-20 Created: 2015-05-12 Last updated: 2015-05-20Bibliographically approved

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