Green light LED activated ligation of a scalable, versatile chalcone chromophore
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De Bruycker, Kevin
Micallef, Aaron S
Walden, Sarah L
Frisch, Hendrik
Barner-Kowollik, Christopher
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Abstract
Herein we introduce a photoreactive chalcone moiety that can be synthesized at a scale of several grams with ease, and efficiently undergoes a [2 + 2] photocycloaddition with light up to just below 500 nm as determined by an action plot. The peak chalcone reactivity is at 440 nm which is red-shifted by 25 nm compared to the absorption maximum at 415 nm. The chalcone was attached to a RAFT agent enabling reversible deactivation radical polymerization. The resulting polymer subsequently took part in a photoligation triggered by light from an LED centered at 505 nm. Thus, we introduce a chalcone that is capable of overcoming the synthetic disadvantages associated with styrylpyrenes and can readily undergo [2 + 2] photocycloadditon with visibile light.
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Polymer Chemistry
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12
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34
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Distributed under the terms of the Creative Commons Attribution-NonCommercial 4.0 International License, which permits unrestricted, non-commercial use, distribution and reproduction in any medium, providing that the work is properly cited.
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Macromolecular and materials chemistry
Physical chemistry
Nanotechnology
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Irshadeen, IM; De Bruycker, K; Micallef, AS; Walden, SL; Frisch, H; Barner-Kowollik, C, Green light LED activated ligation of a scalable, versatile chalcone chromophore, Polymer Chemistry, 12 (34), pp. 4903-4909