Dataset Information

Thiol-ene/oxidation tandem reaction under visible light photocatalysis: synthesis of alkyl sulfoxides.

ABSTRACT: The photocatalyzed synthesis of sulfoxides from alkenes and thiols has been carried out using Eosin Y. This is a metal-free method which uses a low catalyst loading, atmospheric oxygen as the oxidant, and visible light conditions (green light). A mechanism has been proposed that is consistent with the experimental results.

SUBMITTER: Guerrero-Corella A

PROVIDER: S-EPMC5779077 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Thiol-ene/oxidation tandem reaction under visible light photocatalysis: synthesis of alkyl sulfoxides.

Guerrero-Corella Andrea A María Martinez-Gualda Ana A Ahmadi Fereshteh F Ming Enrique E Fraile Alberto A Alemán José J Alemán José J

Chemical communications (Cambridge, England) 20170901 75

The photocatalyzed synthesis of sulfoxides from alkenes and thiols has been carried out using Eosin Y. This is a metal-free method which uses a low catalyst loading, atmospheric oxygen as the oxidant, and visible light conditions (green light). A mechanism has been proposed that is consistent with the experimental results. ...[more]

PMID: 28890975

Similar Datasets

Project description:The mechanical properties of synthetic hydrogels traditionally have been controlled with the concentration, molecular weight, or stoichiometry of the macromolecular building blocks used for hydrogel formation. Recently, the rate of formation has been recognized as an important and effective handle for controlling the mechanical properties of these water-swollen polymer networks, owing to differences in network heterogeneity (e.g., defects) that arise based on the rate of gelation. Building upon this, in this work, we investigate a rate-based approach for controlling mechanical properties of hydrogels both initially and temporally with light. Specifically, synthetic hydrogels are formed with visible light-initiated thiol-ene 'click' chemistry (PEG-8-norbornene, dithiol linker, LAP photoinitiator with LED lamp centered at 455 nm), using irradiation conditions to control the rate of formation and the mechanical properties of the resulting hydrogels. Further, defects within these hydrogels were subsequently exploited for temporal modulation of mechanical properties with a secondary cure using low doses of long wavelength UV light (365 nm). The elasticity of the hydrogel, as measured with Young's and shear moduli, was observed to increase with increasing light intensity and concentration of photoinitiator used for hydrogel formation. In situ measurements of end group conversion during hydrogel formation with magic angle spinning (MAS 1H NMR) correlated with these mechanical properties measurements, suggesting that both dangling end groups and looping contribute to the observed mechanical properties. Dangling end groups provide reactive handles for temporal stiffening of hydrogels with a secondary UV-initiated thiol-ene polymerization, where an increase in Young's modulus by a factor of ~ 2.5x was observed. These studies demonstrate how the rate of photopolymerization can be tuned with irradiation wavelength, intensity, and time to control the properties of synthetic hydrogels, which may prove useful in a variety of applications from coatings to biomaterials for controlled cell culture and regenerative medicine.

Dataset Information

Thiol-ene/oxidation tandem reaction under visible light photocatalysis: synthesis of alkyl sulfoxides.

Publications

Thiol-ene/oxidation tandem reaction under visible light photocatalysis: synthesis of alkyl sulfoxides.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets