Issue 34, 2021

Green light LED activated ligation of a scalable, versatile chalcone chromophore

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.

Graphical abstract: Green light LED activated ligation of a scalable, versatile chalcone chromophore

Supplementary files

Article information

Article type
Paper
Submitted
08 رمضان 1442
Accepted
11 ذو القعدة 1442
First published
11 ذو القعدة 1442

Polym. Chem., 2021,12, 4903-4909

Green light LED activated ligation of a scalable, versatile chalcone chromophore

I. M. Irshadeen, K. De Bruycker, A. S. Micallef, S. L. Walden, H. Frisch and C. Barner-Kowollik, Polym. Chem., 2021, 12, 4903 DOI: 10.1039/D1PY00533B

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