Synthesis of novel trithiocarbonate and allyl sulfide containing monomers

Fenoli, Christopher R.; Bowman, Christopher N.

doi:10.1039/c3py00709j

Cited by 22 publications

(29 citation statements)

References 19 publications

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“…See Supporting Information, Section S1 for the complete synthetic detail as well as the NMR analysis of the product. 2‐methylene‐propane‐1,3‐(thioethyl acrylate) was synthesized according to a method described in the literature . All the other compounds were obtained from Sigma–Aldrich.…”

Section: Methodsmentioning

confidence: 99%

Photoinduced Diffusion Through Polymer Networks

et al. 2014

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Photomediated addition-fragmentation chemistry is applied to demonstrate the precisely controlled diffusion of chemical species through polymer networks. Fluorescent groups connected to polymer networks by allyl sulfide moieties become mobile upon irradiation with UV light due to radical-mediated addition-fragmentation bond exchange. Photoinduced transport through the bulk, into solution, and across film interfaces is demonstrated.

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Section: Methodsmentioning

confidence: 99%

Photoinduced Diffusion Through Polymer Networks

et al. 2014

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“…Phenyl TTC diacrylate was synthesized following a previously published methodology. 20 To a solution of potassium carbonate (2 eq) in acetonitrile was added 1 equivalent of carbon disulfide. The reaction was heated to 40 C for 30 min as the solution turned a deep red color.…”

Section: Methodsmentioning

confidence: 99%

“…Bisphenol A ethoxylate diacrylate (BisEDA, Sigma Aldrich), pentaerythritol tetrakis(3‐mercaptopropionate) (PETMP, Bruno Bock), and 2,2‐dimethoxy‐2‐phenylacetophenone (DMPA, Sigma Aldrich) were used as received. Phenyl TTC diacrylate was synthesized following a previously published methodology . To a solution of potassium carbonate (2 eq) in acetonitrile was added 1 equivalent of carbon disulfide.…”

Section: Methodsmentioning

confidence: 99%

Influence of small amounts of addition‐fragmentation capable monomers on polymerization‐induced shrinkage stress

Wydra

Fenoli

Cramer

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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The effects of the addition of small amounts of multifunctional monomers that contain functional groups capable of undergoing addition-fragmentation during radical polymerizations are investigated. Specifically, up to 6 wt % of phenyl trithiocarbonate (TTC)-containing diacrylate was added to conventional thiol-multiacrylate photopolymerizations where its addition led to up to 60% reduction in polymerization-induced shrinkage stress. The higher levels of TTC achieve the lowest stress though they also significantly depress the polymerization rate. Using up to 0.5 wt % phenyl TTC successfully reduces the stress by nearly 20%, demonstrating the effectiveness of the phenyl TTC, while minimizing the influence that the RAFT activity of the TTC unit has on the polymerization rate. When the polymerization rates of the TTC-containing resins are increased by changing the incident light intensity, complete acrylate conversion is achieved and the stress remains up to 40% lower in the TTC-containing resins.

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“…The chain exchange offered by the allyl sulfide functional group is limited to the consumption of the activating radical spices. [ 201 ] To overcome this limit in reversibility, “living” hydrogels (i.e. hydrogels where the activating radical species regenerate by themselves) were produced by patterning peptides and proteins, introducing a cycle of two thiol‐ene photo‐induced click chemistry reactions.…”

Section: Fabrication Of Patterns By Precise Chemical Designmentioning

confidence: 99%

3D Patterning within Hydrogels for the Recreation of Functional Biological Environments

Primo

Mata

2021

Adv Funct Materials

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Biological structures are inherently complex in nature. Structural hierarchy, chemical anisotropy, and compositional heterogeneity are ubiquitous in biological systems and play a key role in the functionality of living systems. For decades, methods such as soft lithography have enabled recreation of such arrangements through precise spatial control of molecular patterns in 2D. With technological advances and increasing understanding of molecular and structural biology, there has been an increasing interest in recreating such spatial organizations in 3D. In this review, a comprehensive summary of the latest technologies being used to create 3D patterns of functional molecules within hydrogels for tissue engineering applications is presented. The review is divided into five groups of technologies defined according to the main driving force used to fabricate the patterns including light, precise chemical design, microfluidics, 3D printing, and non‐contact forces (i.e. electric, magnetic, or acoustic fields and self‐assembly).

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Synthesis of novel trithiocarbonate and allyl sulfide containing monomers

Cited by 22 publications

References 19 publications

Photoinduced Diffusion Through Polymer Networks

Photoinduced Diffusion Through Polymer Networks

Influence of small amounts of addition‐fragmentation capable monomers on polymerization‐induced shrinkage stress

3D Patterning within Hydrogels for the Recreation of Functional Biological Environments

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