A light-activated reaction manifold

Hiltebrandt, Kai, Elies, Katharina, D'hooge, Dagmar R., Blinco, James P., & Barner-Kowollik, Christopher (2016) A light-activated reaction manifold. Journal of the American Chemical Society, 138(22), pp. 7048-7054.

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Abstract

We introduce an efficient reaction manifold where the rate of a thermally induced ligation can be controlled by a photonic field via two competing reaction channels. The effectiveness of the reaction manifold is evidenced by following the transformations of macromolecular chain termini via high-resolution mass spectrometry and subsequently by selective block copolymer formation. The light-controlled reaction manifold consists of a so-called o-quinodimethane species, a photocaged diene, that reacts in the presence of light with suitable enes in a Diels–Alder reaction and undergoes a transformation into imines with amines in the absence of light. The chemical selectivity of the manifold is controlled by the amount of ene present in the reaction and can be adjusted from 100% imine formation (0% photo product) to 5% imine formation (95% photo product). The reported light-controlled reaction manifold is highly attractive because a simple external field is used to switch the selectivity of specific reaction channels.

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ID Code: 95699
Item Type: Journal Article
Refereed: Yes
DOI: 10.1021/jacs.6b01805
ISSN: 1520-5126
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Copyright Owner: Copyright 2016 American Chemical Society
Deposited On: 05 Jul 2016 22:24
Last Modified: 06 Jul 2016 23:39

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