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Usage

Uses

Used in Polymer Synthesis:
Bis[2-(2′-bromoiso-butyryloxy)ethyl]disulfide is used as an ATRP initiator for the preparation of biodegradable polymers. This application is crucial for creating environmentally friendly materials that can break down over time, reducing the environmental impact of plastic waste.
Used in Gold Surface Adhesion:
In the field of materials science, Bis[2-(2′-bromoiso-butyryloxy)ethyl]disulfide is used as an ATRP initiator to produce polymers that adhere to gold surfaces. This property is valuable for applications such as the development of sensors, electronic devices, and other technologies that require stable and durable gold-polymer interfaces.
Used in Temperature and Light Sensitive Polymers:
Bis[2-(2′-bromoiso-butyryloxy)ethyl]disulfide is also used to introduce a temperature and light-sensitive cleavable region into polymers. This feature allows for the controlled degradation or alteration of the polymer's properties under specific conditions, which can be beneficial in various applications, such as drug delivery systems or self-healing materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Bis[2-(2′-bromoiso-butyryloxy)ethyl]disulfide can be used as a component in the development of drug delivery systems. Its ability to introduce temperature and light-sensitive cleavable regions into polymers can enable the design of smart drug delivery systems that release their payload in response to specific environmental triggers.
Used in Environmental Applications:
Bis[2-(2′-bromoiso-butyryloxy)ethyl]disulfide's role in the synthesis of biodegradable polymers makes it a valuable component in the development of eco-friendly materials. These materials can be used in various environmental applications, such as biodegradable packaging or agricultural films, to reduce plastic pollution and promote sustainability.

Upstream product

• 1892-29-1 bis(2-hydroxyethyl) disulfide 
• 2052-01-9 2-bromo-2-methylpropionic acid 
• 20769-85-1 2-bromoisobutyric acid bromide 

Relevant academic research and scientific papers

A facile route to end-functionalised polymers synthesised by SET-LRP via a one-pot reduction/thiol-ene Michael-type addition

We report the facile synthesis of well defined, disulfide containing polymers via SET-LRP. A one-pot reduction/conjugation reaction enables post polymerisation modification with functional (meth)acrylates and acrylamides.

Plasmonic vesicles of amphiphilic gold nanocrystals: Self-assembly and external-stimuli-triggered destruction

We have developed a new class of plasmonic vesicular nanostructures assembled from amphiphilic gold nanocrystals with mixed polymer brush coatings. One major finding is that the integration of gold nanocrystals (nanoparticles and nanorods) with two types of chemically distinct polymer grafts, which are analogous to block copolymers as a whole, creates a new type of hybrid building block inheriting the amphiphilicity-driven self-assembly of block copolymers to form vesicular structures and the plasmonic properties of the nanocrystals. In contrast to other vesicular structures, the disruption of the plasmonic vesicles can be triggered by stimulus mechanisms inherent to either the polymer or the nanocrystal. Recent advances in nanocrystal synthesis and controlled surface-initiated polymerization have opened a wealth of possibilities for expanding this concept to other types of nanocrystals and integrating different types of nanocrystals into multifunctional vesicles. The development of multifunctional vesicles containing stimuli-responsive polymers could enable their broader applications in biosensing, multimodality imaging, and theragnostic nanomedicine.

Antibacterial effects of poly(2-(dimethylamino ethyl)methacrylate) against selected gram-positive and gram-negative bacteria

Antimicrobial coatings can reduce the occurrence of medical device-related bacterial infections. Poly(2-(dimethylamino ethyl)methacrylate) (pDMAEMA) is one such polymer that is being researched in this regard. The aims of this study were to (1) elucidate pDMAEMA's antimicrobial activity against a range of Gram-positive and Gram-negative bacteria and (2) to investigate its antimicrobial mode of action. The methods used include determination of minimum inhibitory concentration (MIC) values against various bacteria and the effect of pH and temperature on antimicrobial activity. The ability of pDMAEMA to permeabilise bacterial membranes was determined using the dyes 1-N-phenyl-naphthylamine and calcein-AM. Flow cytometry was used to investigate pDMAEMA's capacity to be internalized by bacteria and to determine effects on bacterial cell cycling. pDMAEMA was bacteriostatic against Gram-negative bacteria with MIC values between 0.1-1 mg/mL. MIC values against Gram-positive bacteria were variable. pDMAEMA was active against Gram-positive bacteria around its pKa and at lower pH values, while it was active against Gram-negative bacteria around its pKa and at higher pH values. pDMAEMA inhibited bacterial growth by binding to the outside of the bacteria, permeabilizing the outer membrane and disrupting the cytoplasmic membrane. By incorporating pDMAEMA with erythromycin, it was found that the efficacy of the latter was increased against Gram-negative bacteria. Together, the results illustrate that pDMAEMA acts in a similar fashion to other cationic biocides.

A new class of biochemically degradable, stimulus-responsive triblock copolymer gelators

(Graph Presented) To rub gel into the wound: A thermoresponsive ABA triblock copolymer gelator with A=N-isopropylacrylamide and B=2- (methacryloyloxy)ethyl phosphorylcholine has been synthesized by atom transfer radical polymerization by using a bifunctional disulfide-based initiator. This triblock copolymer forms free-standing peptide-degradable micellar gels under physiologically relevant conditions.

Preparation of stimuli responsive polycaprolactone membranes of controllable porous morphology via combined atom transfer radical polymerization, ring-opening polymerization and thiol-yne click chemistry

Linear di-block copolymers of poly(N-isopropylacrylamide) (PNIPAM) with a center disulfide linkage were prepared by atom transfer radical polymerization (ATRP) of N-isopropylacrylamide (NIPAM) using a bifunctional disulfide-based initiator. The center disulfide bond was cleaved by reduction with excess dl-1,4-dithiothreitol (DTT) to form thiols. The resulting thiol-terminated PNIPAM chains were conjugated to alkyne-terminated poly(ε-caprolactone) (PCL) via UV-initiated thiol-yne click reaction to produce the PCL-click-PNIPAM AB2-type copolymers. The PCL-click-PNIPAM copolymers were cast by phase inversion in an aqueous medium into microporous membranes of well-defined and uniform pores. The PNIPAM content in the PCL-click-PNIPAM copolymers could be used to control the pore size and porosity of the resulting membranes. The PCL-click-PNIPAM-b-PNaSS membrane was prepared via surface-initiated ATRP of sodium 4-styrenesulfonate (NaSS) from the PCL-click-PNIPAM membrane and pore surfaces. The temperature and electrolyte responsive characteristics of the PCL-click-PNIPAM and PCL-click-PNIPAM-b-PNaSS membranes were illustrated in the swelling behavior and controlled glucose transport through the membranes. These stimuli responsive membranes with controllable morphology and low cytotoxicity have potential applications in biomedical engineering, drug delivery and tissue engineering. The Royal Society of Chemistry 2012.

Effect of disulphide loop length on mechanochemical structural stability of macromolecules

In Nature, numerous proteins have evolved to perform similar roles, such as mechanical energy dispersion in different tissues. These biological macromolecules obtain their function from their tertiary structure, but proteins with similar roles can be quite different from each other, making it hard to define what structural features could be mimicked in synthetic materials in order to improve their performance. Here, we introduce an important protein feature-disulphide loops-into synthetic polymers and study the role of the loop size on mechanical energy dispersion. By stressing these polymers in solution, we were able to show, experimentally, that the loop size, up to a certain level, has a significant effect on the chain mechanochemical fragmentation rate, indicating it is affecting the polymer unfolding in solution prior to mechanochemical scission of the polymer backbone. Importantly, this experimental study uses homopolymers, providing information on an individual parameter-loop size-which cannot be obtained from comparing different proteins. This research emphasises the use of tailor-designed polymer-peptide hybrids to study fundamental questions on protein tertiary structures.

Enzymatically Degassed Surface-Initiated Atom Transfer Radical Polymerization with Real-Time Monitoring

Polymer brush coatings are frequently prepared by radical polymerization, a notoriously oxygen sensitive process. Glucose oxidase (GOx) can inexpensively enable radical polymerization in solution by enzymatically consuming oxygen as it oxidizes glucose. Here, we report the growth of polymeric brushes using GOx-assisted atom transfer radical polymerization (ATRP) from a surface while open to air. Specifically, we grew a set of biomedically relevant polymer brushes, including poly(oligo(ethylene glycol) methacrylate) (POEGMA), poly(2-dimethylaminoethyl methacrylate) (PDMAEMA), poly(sulfobetaine methacrylate) (PSBMA), and poly(2-(methylsulfinyl)ethyl acrylate (PMSEA). For each of these polymers, we monitored GOx-assisted and GOx-free ATRP reaction kinetics in real time using quartz crystal microbalance (QCM) and verified findings with localized surface plasmon resonance (LSPR). We modeled brush growth kinetics considering bimolecular termination. This model fit our data well (r2 > 0.987 for all samples) and shows the addition of GOx increased effective kinetic chain lengths, propagation rates, and reproducibility. We tested the antifouling properties of the polymer brush coatings against human blood plasma and were surprised to find that coatings prepared with GOx repelled more plasma proteins in all cases than their GOx-free counterparts.

Combining atom transfer radical polymerization and disulfide/thiol redox chemistry: A route to well-defined (bio)degradable polymeric materials

Linear well-defined degradable polymethacrylates with internal disulfide link were prepared by atom transfer radical polymerization (ATRP) of methyl, terf-butyl, and benzyl methacrylate using bis[2-(2-bromoisobutyryloxy)ethyl] disulfide as the initiator and CuBr/2,2'-bipyridine as the catalyst at 50°C. The disulfide bond was cleaved to thiol by reduction with tributylphosphine, yielding polymers of half the molecular weight of the starting materials. Degradable gels were prepared by the copolymerization of methyl methacrylate and a disulfide-containing difunctional methacrylate, bis(2-methacryloyloxyethyl) disulfide, using similar reaction conditions. The produced gels were reduced with tributylphosphine to form soluble, low molecular weight linear polydnethyl methacrylate) fragments containing thiol groups at the chain end and along the backbone, originating from the disulfide difunctional initiator and monomer, respectively. The disulfide-cross-linked gels were further used as "supennacroinitiators" for the bulk ATRP of styrene at 90°C, employing CuBr/N,N,N'N'',N''-pentamethyldiethylenetriamine as the catalyst. The length of the polystyrene pendant chains could be controlled by varying the reaction time. The prepared gels with segmented structure swelled more than the starting polymethacrylate gels in both THF and toluene. Degradation experiments confirmed the high degree of chain-end bromine functionalization of the "supermacroinitiators".

Directing self-assembly of nanoparticles at water/oil interfaces

Finding the right angle: The contact angle of nanoparticles at the water/oil interface can be engineered close to 90° by capping with ligands containing carboxylic ester terminal groups. This drives the nanoparticles to self-assemble into close-packed films (see picture), and thus provides the opportunity to create two- or three-dimensional homo- or heterogeneous nanostructures for electronic, optoelectrical, and magnetic applications.