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Usage

Uses

Used in Polymer Synthesis:
Bis(dodecylsulfanylthiocarbonyl) disulfide is used as a RAFT agent for the controlled radical polymerization of certain monomers. It allows for the precise control of molecular weight and polydispersity, which is crucial for producing polymers with specific characteristics and applications.
Used in Material Science:
In the field of material science, Bis(dodecylsulfanylthiocarbonyl) disulfide is employed to synthesize polymers with tailored properties. These polymers can be used in various applications, such as coatings, adhesives, and composite materials, where controlled polymerization ensures optimal performance.
Used in Pharmaceutical and Biomedical Applications:
Bis(dodecylsulfanylthiocarbonyl) disulfide is utilized in the synthesis of biocompatible and biodegradable polymers for drug delivery systems and medical devices. The controlled polymerization enabled by this RAFT agent allows for the creation of polymers with specific degradation rates and drug release profiles, improving the efficacy and safety of pharmaceutical products.
Used in Environmental Applications:
This RAFT agent is also used in the development of environmentally friendly polymers, such as those designed for water treatment or bioremediation. The controlled polymerization process allows for the synthesis of polymers with specific adsorption or degradation properties, contributing to the development of sustainable solutions for environmental challenges.

Upstream product

• 26960-77-0 sodium dodecanethiolate 
• 112-55-0 1-dodecylthiol 
• 75-15-0 carbon disulfide 

Relevant academic research and scientific papers

Activating ATRP Initiators to Incorporate End-Group Modularity into Photo-RAFT Polymerization

Heterogeneous photocatalysis is increasingly used in reversible deactivation radical polymerization (RDRP). In this study, we found that alkyl bromide redox chemistry typically found in atom transfer radical polymerization (ATRP) can be incorporated in concert with dithiocarbonyl disulfide chemistry into the reversible addition-fragmentation chain transfer (RAFT) process via bismuth oxide photocatalysis. This amalgamation of mechanisms introduces end-group modularity - a new layer of control - into RAFT polymers uniquely enabled by photoredox catalysis. We found that a diversity of functionality can be installed at the α-end group via alkyl bromides, while the molecular weight distribution can be tuned seamlessly at the ω-end group through the simultaneous addition of multiple disulfides.

Synthesis of a new triple-responsive biocompatible block copolymer: Self-assembled nanoparticles as potent anticancer drug delivery vehicle

There has been a continuous effort towards a synthesis of new stimuli-responsive polymer nanoparticle systems for improved cancer chemotherapy over the last decade. In this context, we have presently developed a temperature, pH, and redox-responsive amphiphilic block-copolymer capable of forming nanoparticles in the aqueous medium, targeted towards drug delivery applications. The copper-catalyzed azide-alkyne cycloaddition reaction was utilized to tie the ends of two copolymers - a thermo-responsive poly(N-isopropylacrylamide) based copolymer with an azide end group and a pH-responsive hydrophobic polymer with redox responsive disulfide bond and an alkyne end group, producing a new triple responsive amphiphilic block copolymer (PHNP) that self-assemble in water to produce nanoparticles. Upon heating above the cloud point of poly(N-isopropylacrylamide), these nanoparticles experienced further aggregation to produce larger sized particles as measured by dynamic light scattering, UV–visible spectroscopy, and scanning electron microscopy techniques. PHNP was found to be capable of encapsulating drugs like doxorubicin (DOX) and also fluorescent probes alike Nile Red. The drug release kinetics divulged that in a period of 24 h more than 90percent of the encapsulated DOX was released in pH 5.4 buffer having 10 mM glutathione (GSH) at 40 °C, an environment prevailing in cancer tissues. In vitro studies including live-dead assay and rhodamine-DAPI staining showed that PHNP was non-cytotoxic. DOX-loaded PHNP was observed to be more effective in prohibiting bone cancer cell (MG63) line in comparison to free DOX, demonstrated by the significant reduction of IC50 values. The uptake studies showed that DOX-encapsulated PHNP was more effective for morphometric distortion of MG63 cells in comparison to bare DOX. Therefore, the present research on the development of a biocompatible thermal, pH, and redox-responsive polymer opens up new opportunities in the area of polymeric carrier systems for drug delivery to cancer cells.

CO2-Activated Reversible Transition between Polymersomes and Micelles with AIE Fluorescence

Fluorescent polymersomes with both aggregation-induced emission (AIE) and CO2-responsive properties were developed from amphiphilic block copolymer PEG-b-P(DEAEMA-co-TPEMA) in which the hydrophobic block was a copolymer made of tetraphenylethene functionalized methacrylate (TPEMA) and 2-(diethylamino)ethyl methacrylate (DEAEMA) with unspecified sequence arrangement. Four block copolymers with different DEAEMA/TPEMA and hydrophilic/hydrophobic ratios were synthesized, and bright AIE polymersomes were prepared by nanoprecipitation in THF/water and dioxane/water systems. Polymersomes of PEG45-b-P(DEAEMA36-co-TPEMA6) were chosen to study the CO2-responsive property. Upon CO2 bubbling vesicles transformed to small spherical micelles, and upon Ar bubbling micelles returned to vesicles with the presence of a few intermediate morphologies. These polymersomes might have promising applications as sensors, nanoreactors, or controlled release systems.

Synthesis of block and graft copolymers of styrene by raft polymerization, using dodecyl-based trithiocarbonates as initiators and chain transfer agents

A series of dodecyl-based monofunctional trithiocarbonate chain transfer agents (CTAs) were successfully synthesized, toward the reversible addition-fragmentations chain transfer (RAFT) polymerization of styrene. The CTAs were used as initiators for RAFT

Facile preparation of bis(thiocarbonyl)disulfides via elimination

A robust facile synthetic preparation of bis(thiocarbonyl)disulfides is presented. The route follows an elimination mechanism rather than the more common oxidation. Addition of p-tosyl chloride to a thiocarbonyl thiolate results in the elimination of the chloride by the trithiocarbonate anion and subsequent elimination of the tosyl leaving group (by a second thiocarbonyl thiolate). The side products of the reaction are bis(4-methylphenyl)disulfone and tosylate salts/acids.

SYNTHESIS OF TRITHIOCARBONATE RAFT GENTS AND INTERMEDIATES THEREOF

This invention provides an efficient method for synthesizing trithiocarbonate RAFT agents, RSC(S)SR’, that can be used in the living polymerization of methacrylates and other olefinic monomers. This invention also provides an efficient method of synthesizing bis(alkylsulfanylthiocarbonyl) disulfides that are useful as intermediates in the synthesis of trithiocarbonate RAFT agents.

Redox Reactions in Non-aqueous Media. Determination of Xanthates and Organotrithiocarbonates (Thioxanthates) with Iron(III) in Acetonitrile

The use of iron(III) perchlorate (in acetonitrile) for the visual, potentiometric and spectrophotometric determination of xanthates and organotrithiocarbonates (thioxanthates) in acetonitrile medium is described.The proposed methods are simple, accurate and reliable and show the promise of wide applicability.