In this article, we report the formation of micelles from a tetrathiafulvalene (TTF) end-functionalized poly(N-isopropylacrylamide) (poly(NIPAM)) derivative (1). We have determined the critical aggregation concentration (CAC) and average diameter of the micelles using fluorescence spectroscopy and dynamic light scattering experiments, respectively. We have exploited the NIPAM backbone of the polymer to thermally transform the swollen hydrophilic poly(NIPAM) derivative to a more globular hydrophobic state at the lower critical solution temperature (LCST). Finally, we have shown that we can exploit the chemical oxidation and complexation properties of the TTF unit to disrupt the micelle architecture to release the hydrophobic dye Nile Red from the interior of the micelle.
An easy and environmentally friendly chemical method for the simultaneous reduction and noncovalent functionalization of graphene oxide (GO) using dopamine derivatives is described. The reaction takes place at room temperature under ultrasonication of an aqueous suspension of GO and a dopamine derivative. X-ray photoelectron spectroscopy, FT-IR spectroscopy, and cyclic voltammetry characterizations revealed that the resulting material consists of graphene functionalized with the dopamine derivative. This one-step protocol is applied for simultaneous reduction and functionalization of graphene oxide with a dopamine derivative bearing an azide function. The chemical reactivity of the azide function was demonstrated by a postfunctionalization with ethynylferrocene using the Cu(I) catalyzed 1,3-dipolar cyloaddition.
The synthesis of multifunctional magnetic nanoparticles (MF-MPs) is one of the most active research areas in advanced materials as their multifunctional surfaces allow conjugation of biological and chemical molecules, thus making it possible to achieve target-specific diagnostic in parallel to therapeutics. We report here a simple strategy to integrate in a one-step reaction several reactive sites onto the particles. The preparation of MF-MPs is based on their simultaneous modification with differently functionalized dopamine derivatives using simple solution chemistry. The formed MF-MPs show comparable magnetic properties to those of naked nanoparticles with almost unaltered particle size of around 25 nm. The different termini, amine, azide and maleimide functions, enable further functionalization of MF-MPs by the grafting-on approach. Michael addition, Cu(i) catalyzed « click » chemistry and amidation reactions are performed on the MF-MPs integrating subsequently 6-(ferrocenyl)-hexanethiol, horseradish peroxidase (HRP) and mannose.
The article reports on the strong linking of dopamine derivatives as a simple and a versatile strategy for the surface functionalization of hydroxyl-terminated nanodiamond (ND-OH) particles. Azide- (ND-N(3)) or poly-N-isopropylacrylamide-terminated (ND-PNIPAM) particles were obtained from ND-OH particles through the reaction with the corresponding dopamine derivatives. The azide-terminated ND particles were further derivatized with a fluorescent probe, alkynyl-pyrene, via copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition. The modified ND particles were characterized using transmission Fourier transform infrared (FTIR) spectroscopy, UV-vis spectroscopy, electrochemical measurements, thermogravimetric analysis (TGA), and particle size measurements. The surface loading of ND particles with dopamine was estimated from TGA and UV-vis spectroscopy and was found to be around 0.27 mmol g(-1). Because of its simple, gentle nature and versatility, the chemistry developed in this work can be used as an avenue for the preparation of functional nanodiamond particles for various applications.
Well-defined dopamine end-functionalized polymers were synthesized by employing the reversible addition–fragmentation chain transfer (RAFT) polymerization technique. tert-Butyl acrylate, N-isopropylacrylamide, and styrene monomers were polymerized in the presence of azobis (isobutyronitrile) and a new catechol-based biomimetic RAFT agent incorporating a trithiocarbonate unit. All RAFT polymerizations exhibited pseudofirst-order kinetics, a linear increase of the number-average molar mass (M
n SEC) with conversion and narrow molar mass distributions (polydispersity <1.2). The resulting homopolymers exhibited the electroactive catechol and the ω-trithiocarbonyl end groups. Subsequent immobilization of dopamine end-functionalized polymers on titanium surfaces was monitored by using a surface plasmon resonance (SPR) sensor, and the resulting films were characterized by contact angle, infrared ATR spectroscopy, atomic force microscopy (AFM), and X-ray photoelectron spectroscopy (XPS).
This paper describes the label-free detection of carbohydrate-lectin interactions. The sensor consists of a boron-doped diamond (BDD) electrode terminated with alkynyl surface groups, which have been functionalized via the CuACC (copper(I)-catalyzed azide-alkyne cycloaddition) "click" reaction with carbohydrate analogues bearing an azido-terminating arm. In this work, electrochemical impedance spectroscopy (EIS) was used as an effective technique to probe the specific interactions of the surface-bound carbohydrates with their complementary lectin partners, and the response was found to be dependent on the relative density of sugar units immobilized on the BDD surface. A BDD interface with 60% surface-bound mannose showed a detection limit of ∼5 ± 0.5 nM for Lens culinaris lectin, with an affinity constant of K(A) = (2.63 ± 0.5) × 10(6) M(-1).
A new class of polymeric thermometers with a memory function is reported that is based on the supramolecular host–guest interactions of poly(N‐isopropylacrylamide) (PNIPAM) with side‐chain naphthalene guest moieties and the tetracationic macrocycle cyclobis(paraquat‐p‐phenylene) (CBPQT4+) as the host. This supramolecular thermometer exhibits a memory function for the thermal history of the solution, which arises from the large hysteresis of the thermoresponsive LCST phase transition (LCST=lower critical solution temperature). This hysteresis is based on the formation of a metastable soluble state that consists of the PNIPAM–CBPQT4+ host–guest complex. When heated above the transition temperature, the polymer collapses, and the host–guest interactions are disrupted, making the polymer more hydrophobic and less soluble in water. Aside from providing fundamental insights into the kinetic control of supramolecular assemblies, the developed thermometer with a memory function might find use in applications spanning the physical and biological sciences.
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