Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 40, Pages 12195-12199Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201606425
Keywords
near infrared; NITEC; photoinduced cycloaddition; polymer coupling; upconversion
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Funding
- DAAD/ATN
- German Research Council (DFG) [Sonderforschungsbereich 1176, GRK 2039]
- Queensland University of Technology (QUT)
- KIT
- CSC
- DFG [WU 787/2-1]
- Fonds der Chemischen Industrie (FCI) [661548]
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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 (lambda(abs, max) = 346 nm) and UCNPs are irradiated with near-infrared light at 974 nm, 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 in vivo 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 974 nm irradiation.
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