Modification Pathways for Copoly(2‐oxazoline)s Enabling Their Application as Antireflective Coatings in Photolithography

Fimberger, Martin; Behrendt, Andreas; Jakopič, Georg; Stelzer, Franz; Kumbaracı, Volkan; Wiesbrock, Frank

doi:10.1002/marc.201500589

Cited by 8 publications

(4 citation statements)

References 25 publications

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“…Hydrogels from synthetic polymers and biopolymers can be useful in many biomedical applications, such as drug delivery, tissue engineering, wound healing, regenerative medicine, cell therapies, and ophthalmology. The majority of studies on synthetic polymer hydrogels are based on the use of PEG [ 93 ], PVP [ 94 ], poly(vinyl alcohol) (PVA) [ 95 ], poly(hydroxyethyl methacrylate) (PHEMA) [ 96 ], and, more recently, poly(2-oxazoline)s (POx) [ 97 , 98 , 99 , 100 ].…”

Section: Poly(2-isopropenyl-2-oxazoline) In Biomedical Applicationsmentioning

confidence: 99%

Poly(2-isopropenyl-2-oxazoline) as a Versatile Functional Polymer for Biomedical Applications

Kronek,

Minarčíková,

Kroneková

et al. 2024

Polymers

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Functional polymers play an important role in various biomedical applications. From many choices, poly(2-isopropenyl-2-oxazoline) (PIPOx) represents a promising reactive polymer with great potential in various biomedical applications. PIPOx, with pendant reactive 2-oxazoline groups, can be readily prepared in a controllable manner via several controlled/living polymerization methods, such as living anionic polymerization, atom transfer radical polymerization (ATRP), reversible addition–fragmentation transfer (RAFT) or rare earth metal-mediated group transfer polymerization. The reactivity of pendant 2-oxazoline allows selective reactions with thiol and carboxylic group-containing compounds without the presence of any catalyst. Moreover, PIPOx has been demonstrated to be a non-cytotoxic polymer with immunomodulative properties. Post-polymerization functionalization of PIPOx has been used for the preparation of thermosensitive or cationic polymers, drug conjugates, hydrogels, brush-like materials, and polymer coatings available for drug and gene delivery, tissue engineering, blood-like materials, antimicrobial materials, and many others. This mini-review covers new achievements in PIPOx synthesis, reactivity, and use in biomedical applications.

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Section: Poly(2-isopropenyl-2-oxazoline) In Biomedical Applicationsmentioning

confidence: 99%

Poly(2-isopropenyl-2-oxazoline) as a Versatile Functional Polymer for Biomedical Applications

Kronek,

Minarčíková,

Kroneková

et al. 2024

Polymers

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“…Light-emitting diodes (LEDs) [154], solar cells [155] (including thin-film ones [156]), thermophotovoltaics [157], lasers [158], displays [32] and photolithography [159], are among the main emerging applications of ARCs.…”

Section: Applicationsmentioning

confidence: 99%

Antireflective Coatings: Conventional Stacking Layers and Ultrathin Plasmonic Metasurfaces, A Mini-Review

2016

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Reduction of unwanted light reflection from a surface of a substance is very essential for improvement of the performance of optical and photonic devices. Antireflective coatings (ARCs) made of single or stacking layers of dielectrics, nano/microstructures or a mixture of both are the conventional design geometry for suppression of reflection. Recent progress in theoretical nanophotonics and nanofabrication has enabled more flexibility in design and fabrication of miniaturized coatings which has in turn advanced the field of ARCs considerably. In particular, the emergence of plasmonic and metasurfaces allows for the realization of broadband and angular-insensitive ARC coatings at an order of magnitude thinner than the operational wavelengths. In this review, a short overview of the development of ARCs, with particular attention paid to the state-of-the-art plasmonic- and metasurface-based antireflective surfaces, is presented.

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“…These functionalities are of interest for various click reactions, such as copper(I)-catalyzed azide cycloaddition as well as thiol–ene and thiol–yne reactions, which enable facile postfunctionalization of the resulting polymers. Click reactions on PAOx are typically performed by using copolymers and have found many practical applications, such as the introduction of targeting molecules on polymeric chains, coatings of nanoparticles − or stainless steel, − creation of biocompatible materials with anode-selective deposition behavior, , and many others. ,− In addition, postpolymerization modification readily enables the introduction of side-chains that are not compatible with the CROP of 2-oxazolines . Moreover, cross-linking of alkene- and/or alkyne-functionalized PAOx has been applied for the development of hydrogels or core–shell cross-linked nanoparticles. ,,− …”

Section: Introductionmentioning

confidence: 99%

Cation−π Interactions Accelerate the Living Cationic Ring-Opening Polymerization of Unsaturated 2-Alkyl-2-oxazolines

et al. 2020

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Cation−dipole interactions were previously shown to have a rate-enhancing effect on the cationic ring-opening polymerization (CROP) of 2-oxazolines bearing a side-chain ester functionality. In line with this, a similar rate enhancementvia intermolecular cation−π interactionswas anticipated to occur when π-bonds are introduced into the 2-oxazoline side-chains. Moreover, the incorporation of π-bonds allows for facile postfunctionalization of the resulting poly(2-oxazoline)s with double and triple bonds in the side-chains via various click reactions. Herein, a combined molecular modeling and experimental approach was used to study the CROP reaction rates of 2oxazolines with side-chains having varying degrees of unsaturation and side-chain length. The presence of cation−π interactions and the influence of the degree of unsaturation were initially confirmed by means of regular molecular dynamics simulations on pentameric systems. Furthermore, a combination of enhanced molecular dynamics simulations, static calculations, and a thorough analysis of the noncovalent interactions was performed to unravel to what extent cation−π interactions alter the reaction kinetics. Additionally, the observed trends were confirmed also in the presence of acetonitrile as solvent, in which experimentally the polymerization is performed. Most intriguingly, we found only a limited effect on the intrinsic reaction kinetics of the CROP and a preorganization effect in the reactive complex region. The latter effect was established by the unsaturated side-chains and the cationic center through a complex interplay between cation−π, π−π, π−induced dipole, and cation−dipole interactions. These findings led us to propose a two-step mechanism comprised of an equilibration step and a CROP reaction step. The influence of the degree of unsaturation, through a preorganization effect, on the equilibration step was determined with the following trend for the polymerization rates: n-ButylOx < ButenOx < ButynOx ≥ PentynOx. The trend was experimentally confirmed by determining the polymerization rate constants.

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Modification Pathways for Copoly(2‐oxazoline)s Enabling Their Application as Antireflective Coatings in Photolithography

Cited by 8 publications

References 25 publications

Poly(2-isopropenyl-2-oxazoline) as a Versatile Functional Polymer for Biomedical Applications

Poly(2-isopropenyl-2-oxazoline) as a Versatile Functional Polymer for Biomedical Applications

Antireflective Coatings: Conventional Stacking Layers and Ultrathin Plasmonic Metasurfaces, A Mini-Review

Cation−π Interactions Accelerate the Living Cationic Ring-Opening Polymerization of Unsaturated 2-Alkyl-2-oxazolines

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