Near-Infrared Photoinduced Coupling Reactions Assisted by Upconversion Nanoparticles

Lederhose, P., Chen, Z., Müller, R., Blinco, J. P., Wu, S., & Barner-Kowollik, C. (2016) Near-Infrared Photoinduced Coupling Reactions Assisted by Upconversion Nanoparticles. Angewandte Chemie - International Edition.

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Abstract

We introduce nitrile imine-mediated tetrazole-ene cycloadditions (NITEC) in the presence of upconversion nanoparticles (UCNPs) as a powerful covalent coupling tool. When a pyrene aryl tetrazole derivative (λabs, max=346nm) and UCNPs are irradiated with near-infrared light at 974nm, rapid conversion of the tetrazole into a reactive nitrile imine occurs. In the presence of an electron-deficient double bond, quantitative conversion into a pyrazoline cycloadduct is observed under ambient conditions. The combination of NITEC and UCNP technology is used for small-molecule cycloadditions, polymer end-group modification, and the formation of block copolymers from functional macromolecular precursors, constituting the first example of a NIR-induced cycloaddition. To show the potential for invivo applications, through-tissue experiments with a biologically relevant biotin species were carried out. Quantitative cycloadditions and retention of the biological activity of the biotin units are possible at 974nm irradiation. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Impact and interest:

5 citations in Scopus
4 citations in Web of Science®
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ID Code: 99471
Item Type: Journal Article
Refereed: Yes
Additional Information: Export Date: 5 September 2016
Article in Press
CODEN: ACIEF
Correspondence Address: Blinco, J.P.email: j.blinco@qut.edu.au
Keywords: Near infrared, NITEC, Photoinduced cycloaddition, Polymer coupling, Upconversion, Bioactivity, Block copolymers, Coenzymes, Cyanides, Cycloaddition, Nanoparticles, Nitrogen compounds, End-group modification, Macromolecular precursors, Photo-induced, Tetrazole derivatives, Up-conversion, Upconversion nanoparticles, Infrared devices
DOI: 10.1002/anie.201606425
ISSN: 14337851
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 23 Sep 2016 04:42

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