Synthesis of Processable Inorganic‐Organic Hybrid Polymers Based on Poly(silsesquioxanes): Grafting from Polymerization Using ATRP

Kessler, Daniel; Teutsch, Carmen; Théato, Patrick

doi:10.1002/macp.200800146

Cited by 20 publications

(13 citation statements)

References 34 publications

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“…In order to install polymeric α‐amino phosphonic acids onto substrates surfaces, surface KF‐PMR and subsequent deprotection of α‐amino phosphonates have to be conducted on aldehyde‐functionalized substrates surfaces. For this, aldehyde‐functionalized surfaces were prepared by coating of organic–inorganic hybrid polymers featuring aldehyde moieties onto substrates, following our recently reported method . In this context, poly(methylsilsesquioxane)‐poly(4‐vinyl‐benzaldehyde) (PMSSQ–PStCHO) was prepared via reversible addition–fragmentation chain transfer (RAFT) polymerization.…”

Section: Resultsmentioning

confidence: 99%

Installation of Zwitterionic α‐Amino Phosphonic Acid Moieties on Surfaces via a Kabachnik‐Fields Post‐Polymerization Modification

Wagner

Schneider

Michelswirth

et al. 2015

Macro Chemistry & Physics

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An organic-inorganic hybrid polymer, composed of poly(methylsilsesquioxane) (PMSSQ) and poly(4-vinyl benzaldehyde) (PStCHO), is prepared by reversible addition-fragmentation chain transfer (RAFT) polymerization of 4-vinyl benzaldehyde (StCHO) using a macro-chain transfer agent (CTA) based on PMSSQ. The obtained PMSSQ-PStCHO is spin-coated on substrates such as silicon wafers or copper plates to afford aldehyde-functionalized surfaces. Successful Kabachnik-Fields post-polymerization modifi cation (KF-PMR) of the aldehyde-functionalized surfaces is conducted with amines and dialkyl phosphonates, and characterized by surface analysis techniques including IR, energy-dispersive X-ray (EDX), and X-ray photoelectron spectroscopy (XPS) measurements, documenting the installation of α-amino phosphonates onto surfaces with practically quantitative conversion of aldehydes. In addition, the generated α-amino phosphonates are successfully deprotected to afford the corresponding α-amino phosphonic acids on surfaces, which make this route a reliable tool-enabling surface functionalization with α-amino phosphonic acids.surfaces. To expand the scope of functional materials featuring designed surface characteristics, a number of highly reactive and selective reactions, so-called "click reactions", have been employed. This includes Cu(I)-catalyzed and metal-free 1,3-dipolar cycloaddition (CuCAAC) reaction of organo-azides and alkynes, [ 1,2 ] thiol-ene, thiol-maleimide, [ 3 ] nucleophile-isocyanate, [ 4 ] and activated ester-amine reactions, which all realize a facile functionalization of substrate surfaces. [5][6][7][8] In spite of the fact that these click reactions have been employed in surface modifi cation chemistry, the intrinsic drawbacks of these conventional "click reactions" are: 1) only one functionality per one reaction can be achieved and 2) no functionality owing to linkages that are generated via reactions. In order to target material surfaces featuring more sophisticated functionalities, chemists need to propose a synthetic strategy realizing installation two or more functional molecules per single reactive site accompanied with a generation of an attracting linkage.

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Section: Resultsmentioning

confidence: 99%

Installation of Zwitterionic α‐Amino Phosphonic Acid Moieties on Surfaces via a Kabachnik‐Fields Post‐Polymerization Modification

Wagner

Schneider

Michelswirth

et al. 2015

Macro Chemistry & Physics

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“…Theato and coworkers introduced an alternative, yet convenient, method for fabrication of reactive polymer brushes on surfaces by simply spin-coating a precursor hybrid reactive copolymer. For this purpose, poly (methylsilsesquioxane)-poly(pentafluorophenyl acrylate) (PMSSQ-PPFPA) hybrid polymers were comprehensively investigated by the group [56,57]. PMSSQ-PPFPA hybrid polymers were synthesized by RAFT polymerization using a PMSSQ-based inorganic chain transfer agent.…”

Section: Reactive Polymer Brushesmentioning

confidence: 99%

Post-polymerization Modification of Surface-Bound Polymers

Théato

2015

Controlled Radical Polymerization at and From Solid Surfaces

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Surfaces that have been intricately functionalized with reactive polymers have attracted scientific attention recently because of their potential use in a broad range of applications. Polymers containing chemically reactive functional groups can be utilized for subsequent modification of various surfaces. Reactive polymeric surfaces can be produced by surface-initiated polymerization, such as atom transfer radical polymerization, nitroxide-mediated polymerization, and ring-opening metathesis polymerization. Such surfaces can subsequently undergo postpolymerization modification to alter their physicochemical properties. Postpolymerization modification has a number of advantages, including the fact that diverse polymer structures are rapidly accessible without individual synthesis; polymerization of new functional monomers can produce a variety of surfaces and interfaces; and other materials can be easily modified, which would be difficult using conventional direct polymerization. In addition, the libraries of chemical reactions and materials that can be used in post-polymerization modifications are abundant. Therefore, post-polymerization modification opens up new platforms for the facile and versatile modification of various surfaces. This chapter focuses on a discussion of post-polymerization modification of various surface-bound polymers, from planar surfaces to three-dimensional objects, and on the extended applications of the reactive surfaces.

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“…In the present study, we report on the generation of zwitterionic moieties on the poly(methylsilsesquioxane)‐poly(4‐vinyl‐benzaldehyde) (PMSSQ–PStCHO)‐modified silicon surfaces based on surface Kabachnik–Fields reaction ( sur ‐KFR) to install polymeric α‐aminophosphonates and the subsequent deprotection of phosphonate groups (Scheme ) …”

Section: Introductionmentioning

confidence: 99%

Investigation of Antifouling Properties of Surfaces Featuring Zwitterionic α‐Aminophosphonic Acid Moieties

Wagner

Zimmermann

Heisig

et al. 2015

Macromolecular Bioscience

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Zwitterionic thin films containing α-amino phosphonic acid moieties were successfully introduced on silicon surfaces and their antifouling properties were investigated. Initially, the substrates were modified with a hybrid polymer, composed of poly(methylsilsesquioxane) (PMSSQ) and poly(4-vinyl benzaldehyde) (PStCHO). Next, a Kabachnik-Fields post-polymerization modification (sur-KF-PMR) of the functionalized aldehyde surfaces was conducted with different amines and dialkyl phosphonates. After subsequent deprotection reaction of dialkyl phosphonates, the obtained zwitterionic surfaces were characterized by various techniques and we found excellent antifouling properties of the resulting films.

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Synthesis of Processable Inorganic‐Organic Hybrid Polymers Based on Poly(silsesquioxanes): Grafting from Polymerization Using ATRP

Cited by 20 publications

References 34 publications

Installation of Zwitterionic α‐Amino Phosphonic Acid Moieties on Surfaces via a Kabachnik‐Fields Post‐Polymerization Modification

Installation of Zwitterionic α‐Amino Phosphonic Acid Moieties on Surfaces via a Kabachnik‐Fields Post‐Polymerization Modification

Post-polymerization Modification of Surface-Bound Polymers

Investigation of Antifouling Properties of Surfaces Featuring Zwitterionic α‐Aminophosphonic Acid Moieties

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