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Issue 42, 2020, Issue in Progress
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Thiol–ene coupling reaction achievement and monitoring by “in situ” UV irradiation NMR spectroscopy

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Abstract

In this study, the possibilities of a new “in situ” LED UV illumination NMR spectroscopic technique for performing an initiator-free thiol–ene “click” coupling reaction of an allyl-functionalized poly(allyl glycidyl ether) (PAGE) prepolymer with a number of mono- and di-oligo polyethylene glycol (PEG) thiols is demonstrated. The state-of-the-art setup constructed with LEDs as UV light sources that illuminate through optical fibers directly into an NMR testing tube at a fixed wavelength of 365 nm is appropriate for various polymeric materials and biologically active substances. The selected experimental protocol uses a series of periods of irradiation and dark periods, thus providing opportunities to conduct an effective thiol–ene “click” reaction and simultaneously study the kinetics of the photochemical reaction with the exposure time, as well as macromolecular association directly in a solution applying the whole types of NMR methods: from conventional 1H or 13C NMR to diffusion NMR spectroscopy (DOSY). In addition, the molecular mass characteristics of the prepared copolymers were studied by gel-permeation chromatography (GPC). The observed differences in the reaction rates as well as in the size of species formed (the corresponding hydrodynamic radiuses Rh of aggregates) as a result of the coupling process of parent PAGE prepolymers and model PEG thiols were thoroughly discussed and the reaction pathway proposed.

Graphical abstract: Thiol–ene coupling reaction achievement and monitoring by “in situ” UV irradiation NMR spectroscopy

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Article information


Submitted
30 Apr 2020
Accepted
18 Jun 2020
First published
02 Jul 2020

This article is Open Access

RSC Adv., 2020,10, 25214-25222
Article type
Paper

Thiol–ene coupling reaction achievement and monitoring by “in situ” UV irradiation NMR spectroscopy

N. Toncheva-Moncheva, M. Dangalov, N. G. Vassilev and C. P. Novakov, RSC Adv., 2020, 10, 25214
DOI: 10.1039/D0RA03902K

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