Search results for "CLICK CHEMISTRY"

Combining Spontaneous Polymerization and Click Reactions for the Synthesis of Polymer Brushes: A "Grafting Onto" Approach

2013

Two novel benzofulvene monomers bearing propargyl or allyl groups have been synthesized by means of readily accessible reactions, and were found to polymerize spontaneously by solvent removal, in the apparent absence of catalysts or initiators, to give the corresponding polybenzofulvene derivatives bearing clickable propargyl or allyl moieties. The clickable propargyl and allyl groups were exploited in appropriate click reactions to develop a powerful and versatile "grafting onto" synthetic methodology for obtaining tailored polymer brushes.

2018

Hard corona (HC) protein, i.e., the environmental proteins of the biological medium that are bound to a nanosurface, is known to affect the biological fate of a nanomedicine. Due to the size, curvature, and specific surface area (SSA) 3-factor interactions inherited in the traditional 3D nanoparticle, HC-dependent bio-nano interactions are often poorly probed and interpreted. Here, the first HC-by-design case study in 2D is demonstrated that sequentially and linearly changes the HC quantity using functionalized graphene oxide (GO) nanosheets. The HC quantity and HC quality are analyzed using NanoDrop and label-free liquid chromatography-mass spectrometry (LC-MS) followed by principal compon…

Highly Ordered Nanoporous Thin Films from Photocleavable Block Copolymers

2011

Poly(styrene-block-ethylene oxide) with an o-nitrobenzyl ester photocleavable junction (PS-hν-PEO) was synthesized by a combined RAFT polymerization and “click chemistry“ approach and represents the first report utilizing this method for the synthesis of photocleavable block copolymers. After solvent annealing, highly ordered thin films were prepared from PS-hν-PEO. Following a very mild UV exposure and successive washing with water, PS-hν-PEO thin films were transformed into highly ordered nanoporous thin PS films with pore diameters of 15–20 nm and long range ordering (over 2 μm × 2 μm). Afterwards the pores were filled with PDMS by spin-coating in combination with capillary forces. After…

Dynamic Model Metallo‐Supramolecular Dual‐Network Hydrogels with Independently Tunable Network Crosslinks

2020

Transition to Reinforced State by Percolating Domains of Intercalated Brush-Modified Cellulose Nanocrystals and Poly(butadiene) in Cross-Linked Compo…

2013

The classic nanocomposite approach aims at percolation of low fraction of exfoliated individual reinforcing nanoscale elements within a polymeric matrix. By contrast, many of the mechanically excellent biological nanocomposites involve self-assembled and space-filled structures of hard reinforcing and soft toughening domains, with high weight fraction of reinforcements. Here we inspect a new concept toward mimicking such structures by studying whether percolation of intercalated domains consisting of alternating rigid and reinforcing, and soft rubbery domains could allow a transition to a reinforced state. Toward that, we present the functionalization of rigid native cellulose nanocrystals …

Tetrazine Linkers as Plug-and-Play Tags for General Framework Functionalization and C60 Conjugation

2022

The value of covalent post-synthetic modification in expanding the chemistry and pore versatility of reticular solids is well documented. Here we use mesoporous crystals of UiO-68-TZDC to demonstrate the value of tetrazine connectors for all-purpose inverse electron-demand Diels-Alder ligation chemistry. Our results suggest a positive effect of tetrazine reticulation over its reactivity for quantitative one-step functionalization with a broad scope of alkene or alkyne dienophiles into pyridazine and dihydropyridazine frameworks. This permits generating multiple pore environments with diverse chemical functionalities and the expected accessible porosities, that is also extended to the synthe…

N‐Terminal Modification of Gly‐His‐Tagged Proteins with Azidogluconolactone

2021

Site-specific protein modifications are vital for biopharmaceutical drug development. Gluconoylation is a non-enzymatic, post-translational modification of N-terminal HisTags. We report high-yield, site-selective in vitro α-aminoacylation of peptides, glycoproteins, antibodies, and virus-like particles (VLPs) with azidogluconolactone at pH 7.5 in 1 h. Conjugates slowly hydrolyse, but diol-masking with borate esters inhibits reversibility. In an example, we multimerise azidogluconoylated SARS-CoV-2 receptor-binding domain (RBD) onto VLPs via click-chemistry, to give a COVID-19 vaccine. Compared to yeast antigen, HEK-derived RBD was immunologically superior, likely due to observed diffe…

Click chemistry-assisted bioconjugates for hapten immunodiagnostics

2020

Bioorthogonal reactions have revolutionized the way low molecular weight compounds are coupled to biomolecules. Organic chemistry, polymer science, and chemical biology are among the disciplines that are benefited the most from this breakthrough. Despite the reliability of the click chemistry concept for the efficient and chemoselective functionalization of biomacromolecules with haptens at preferred positions, the fact that azide–alkyne cycloaddition reactions originate new chemical moieties as part of the linker may have delayed their application in the immunodiagnostic field. Using the mycotoxin ochratoxin A as a model compound, we herein demonstrate for the first time that bioconjugates…

A new family of "clicked" estradiol-based low-molecular-weight gelators having highly symmetry-dependent gelation ability.

2011

Reported herein is the discovery of a novel family of "clicked" estradiol-based LMWGs whose gelation ability highly depends on the gelator symmetry. These LMWGs that gel different organic solvents in the presence of H(2)O even at concentrations as low as 0.04 wt% are readily accessible using "click" chemistry.

Bioinspired manganese(II) complexes with a clickable ligand for immobilisation on a solid support.

2014

International audience; Clickable ligands like N,N′-bis((pyridin-2-yl)methyl)prop-2-yn-1-amine (L1) and N-((1-methyl-1H-imidazol-2-yl)methyl)-N-(pyridin-2-ylmethyl)prop-2-yn-1-amine (L2) have been used to synthesise a series of manganese(II) complexes for grafting onto appropriate solid supports. These ligands mimic the 2-His-1-carboxylate facial chelation present in the active site of the manganese-dependent dioxygenase (MndD), while the alkyne side function allows grafting of the ligand onto an azido-functionalised support using “click chemistry” methodologies. Such synthetic analogues of the MndD crystallise in the solid state as double halide or pseudohalide-bridged dinuclear manganese(…